I sat outside of Pixar’s main building in late April 2009, tears welling in my eyes. I had just learned that my internship would not be turning into a full-time position—the only intern of the bunch set free. I was being consoled by one of my in-house mentors, Sally (@garbidoll), who assured me that exciting things were ahead, despite my not getting the job I so desperately wanted. “You might be the luckiest intern here,” she told me. “You don’t need to get what you want the first thing out of school. And besides, how do you even know this is what you want? You convinced yourself of it, but now you can try other things, and then decide with a little more experience.” It wasn’t what I wanted to hear; I had spent five years of my life plotting how to get that internship, and even graduated early so that I could work in the Story Department of Toy Story 3, under the studio’s brightest minds, under Oscar-winning screenwriters, and with the idea that I would never in my life have to leave the company. Everything was planned on getting that internship—every extracurricular, every screenwriting class—on staying put, on concepting and producing films with the best of the best. As a bumbling idiot kid from South Dakota, I had already come so far, and this felt like I was the first person voted out in some cruel reality show competition. “I don’t know what the hell to do now,” I said between sobs. “I was supposed to get a job. I was supposed to be here forever.” Bless Sally for being so patient with me then, because I’m embarrassed at how entitled I felt, at how naive I was to think things would pan out so simply at 22. If I were her, I’d have said “Get over your fucking self and grow up, kid.” I was such an idiot.
During that internship, I was secretly seeking out men for hookups on Craigslist. This was all pre-Grindr, pre-Scruff. I drove into San Francisco’s Marina one night. I met a man named Joe—that’s what he called himself, while sounding unsure of it—and told him my name was Leonard (my actual middle name). It’s funny two closeted men felt comfortable having sex but not sharing real names. And of the sex: this was my first time going so far. How romantic that he was a stranger, and that I let him do it without a condom. I left feeling stupid, but mostly just glad I knew what sex felt like, even if it lacked intimacy. When the Pixar internship ended—six weeks after this encounter—my lymph nodes swelled to the size of chickpeas, and I woke each morning in a sweat-soaked bed. I had pink eye twice in a week, and my tongue was furry with candida. I knew what was wrong, and recorded a video on my laptop saying goodbye to my family, sniffling through my apologies for any hurt I would cause them. I planned to disappear; to what degree I did not yet know. It would be the easiest way to escape my own shame, because I hadn’t even convinced myself that I was gay yet (despite the hookups) and now I would have to tell people I was HIV-positive, too. First, though, I needed an official diagnosis. I made an appointment with a testing clinic five days out—unaware that San Francisco is filled with walk-in clinics—and suffered through the week. At the appointment, I showed the counselor my symptoms, and saw great concern wash over his face. We did a rapid test, and he came back with my results: HIV-negative. “Are you having a nervous breakdown, a panic attack? Is everything ok with work?” he asked. I sobbed in his arms for 20 minutes. He was patient. Understanding. He held my hand the entire time, and urged me to please take time off, to grow into myself, to love myself, to be well. To talk to my parents soon. I walked three miles home, with a second chance to do things properly, to not be ashamed. I deleted the pathetic 10-minute video without rewatching it, then vowed to never be so miserable—or so secretive—ever again. I didn’t want to be that version of myself anymore.
To center myself, I drove alone 4,200 miles to Maine. I applied for a summer camp job—as staff photographer—and spent the next two months teaching 11-year-old boys how to not wet the bed and how to use a point-and-shoot camera. (“OK, use auto-focus. Just aim it at whatever. Click the button. Nice. Great pic, kiddo.”) I made out with a few female counselors, still coming to terms with my accepted sexuality. I turned my cell phone off for weeks at a time, and checked my email and Facebook just once a day, shutting out all my friends’ updates of new jobs and good fortune. I needed to not compare myself to them. Instead, I helped kids muster up the courage to ask their crushes to the dance, wrote campfire songs, survived two bouts of bed lice, and hiked the backwoods of New Hampshire. Sometime mid-summer, I realized my lymph nodes had shrunk to their normal size, and that I felt an intoxicating wave of content from having no expectations or saturated plans. How foreign, to feel settled and free of ambition. That calm was short-lived, though, because next came New York, on the $500 I had in savings. I moved in with my college pal Abbey (@afaris24) for a month, rent-free, and a temp agency promised that I would have a job in the entertainment industry in no time. The next day, they offered me a crossing guard position at the Friends Seminary School for $12/hour, helping the children of many famous actors cross safely from the main building to the high school annex. The worst days were when it would downpour, though it at least complemented my mood and the renewed sense of failure. After learning about my writing ambitions, I got an unofficial offer to help teach drama classes to kindergartners. I was offended they would assume it was what I wanted, that teaching drama to privileged children was at all related to screenwriting. I declined, and they didn’t beg me to reconsider. I quit the crossing guard gig after a few weeks, realizing I had approached this move entirely wrong: with no plans or realistic expectations. So I pointed my car home to South Dakota, a terrific place for a closeted man and aspiring screenwriter. I was such an idiot.
When I left Sioux Falls for college in 2005, I vowed to never move back again. I had no plans for such a static, homogenous place in my future. I spent summers at school in hip Lawrence, KS, or interning in San Francisco. So, asking my parents for help and haven at age 23 was a bit humiliating, but they were happy to have me back. And luckily, I had numerous childhood friends who were in the same boat; that’s the Class of 2008 and 2009 for you. I took a job bartending for a restauranteur who had employed me throughout high school. Then one Friday, I got a call from a Vice Principal of a middle school across the street, asking if I wanted to teach seventh grade social studies for the remainder of the year (the current teacher was gravely ill, and they needed a replacement who wouldn’t have to get hired full time the next year. In South Dakota, long-term public substitutes only need a bachelor’s degree, in anything. Seriously.) The following Monday—three days later—I was in the classroom, writing lessons, grading tests, disciplining punk teenagers, and still bartending nights and weekends. Meanwhile, I started exchanging sexual emails with the father of a former classmate. (Thanks, Craigslist.) I nearly met up with him, but backed out when he said “I just need a man to cuddle with sometimes, you know? That’s hard to find here.” It validated why I couldn’t stay in Sioux Falls, why I could never be happy there. Then, I started hanging out with another former classmate—one I had a secret crush on all through middle and high school. He was living at home too, also teaching, also closeted, also wanting out. Seven consecutive days of sexual tension turned into five months of sneak-out-of-the-house-at-2am-and-back-in-at-6am sex, plus cuddling, late night dinners, and validation for having moved home. It was the high school romance I never got; he was my first boyfriend, my impetus for finally coming out to my friends. We broke up after the school year ended, when I had saved enough money to return to the Bay. I knew that breakup was coming, because I was nearly 24 and needed to get the hell out of my dead-end South Dakota. I vowed to never move back again…again.
I drove with my likeminded North Dakotan cousin Jenny (@approximately) across Canada, then south to the Bay. She would spend her collegiate summer living with our aunt Amy (@amycleonard) in her vacant Russian Hill in-law unit (as I had twice done). Amy was the youngest sister of both of our mothers, and had herself fled Dakota for blue oceans, blue politics, and blue jeans; at the time she was heading Levi’s product development. She was proof that we could make a sound and unprescribed living for ourselves. I moved to Berkeley for the summer with childhood friend Britta (@runbmcee), who had also flown the South Dakota coop after a year at home. We house sat for Amy’s colleague, where he and his husband lived with their two biological sons—very Berkeleyan, too: one boy from each father, but from the same mother, who was also present in their lives. We looked after their 13 chickens for the summer. One of them was crippled, which is worth mentioning only because it felt just as Berkeleyan for them to spare her life. She—Clarice—died while I was watching her, of course, because I was still a fuck-up. I spent the summer months holding a production internship with the Telluride Film Festival (based in Berkeley), and my reticent aunt connected me with a modeling agency because I wanted to try fit modeling at Levi’s. With fit modeling, you just try on clothes for the designers, to see how they fit; it seemed so easy and lucrative. The agency said no, since a bunch of firefighters already held the post and weren’t giving it up any time soon. But, they wanted to send me on other calls. So I wasted lots of time in waiting rooms, for no ambitious reason whatsoever. At one call, I heard a group of wannabe models congratulating one guy: “Thad, congrats on the Colgate ad!” Replied Thad: “Thanks. Seven years of waiting tables and going on calls, finally validated. Feels good.” I shook my head subtly and held back my laughter; that was my last waiting room. After summer, I swapped cousin Jenny for the no-rent studio, and took a video-rental-clerk job in North Beach for $7/hour, 12 hours/week. For four months. Because I was still a fuck-up.
Things turned around in December 2010: My aunt convinced me to take a government-run Americorps job with the Bay Area Red Cross. (“You’ve got free rent, they’ll hold your loans, and above all, it’s applicable job experience.”) So, I started managing projects and developing youth programs across six counties, working 40+ hours each week for a $9,000 salary. I count that year a major victory, mostly because I didn’t switch jobs or move. Another win: I was coming into my life as an out gay man. I told my entire family back home, knowing I had the spirited support of my aunt and her family in San Francisco. Luckily, nobody in South Dakota melted into a puddle like I had predicted. I still didn’t talk about my gay life with any of them, though, because I didn’t see how they could possibly relate. There wasn’t exactly a parade held in my honor, either, so you can understand why I shut that part of my life off to anyone less than enthusiastic. In a way I created a whole new version of myself that they didn’t get to meet. I was happy. I had a terrific boyfriend who made me happy—God, that’s not the ticket to happiness, don’t get me wrong, but it played a big part here. He was four years older and, like my aunt, showed me the life I could have, the blissful reality I deserved. He took me to restaurants, to hidden corners of the city, to parties with his friends. He helped me pick out nice clothes, introduced me to his family, and gave me this mold of a life that I knew I wanted. Suddenly, my entire existence in SF was framed by the parameters he and my aunt had built for me. Our boyfriendship lasted six months, and although we sustained it on and off for the next couple seasons, we never were fully on again. That’s because, as my Americorps year ended, my sights were set back on New York City, on properly and permanently landing a film job this time. On being totally independent, on making my own friends and my own life instead of having it handed to me. So, I flew away from free rent, from my Bay Area family, from another relationship, and from the city that gave me enlightenment—to put an end to my bumbling about.
I met Lindsay Zoladz (@lindsayzoladz) in fall 2007 when we were both college juniors, at the Telluride Film Festival’s Student Symposium. Each year they take 50 students with various film-related interests, and those selected get to meet all the filmmakers, see the top awards contenders, and network with other students who share a love for movies. We formed a small clique of six or seven people, saving seats at each theater, staying up late to talk about the films afterwards, and discussing what we hoped to do with our lives after graduation. I wanted to write films, and Lindsay wanted to write about them. We sort of lost touch in the years after the fest, especially since she keeps a low profile on social media. We tried a few times to connect after she moved to New York from Washington DC in late 2012, but both kept rescheduling due to our busied, social lives; I still didn’t know what she was up to here. One day in September 2014, I got my New York Magazine in the mail, and saw at the top of the cover: “Zoladz on Summer’s Pop Sisters.” Surely, there was no other Zoladz, I thought to myself. It was her column, indeed, and it was about the various multiple-female collaborations that dominated airwaves over the summer (think Iggy + Charli, Nicki + Ariana + Jessie J, Beyonce + Nicki), and the curious, sometimes conflicted undertones behind such collabs. I beamed as I read the column on my morning commute, then sent Lindsay a congratulatory text on her new role at @NYMag: Music wasn’t movies, but this was the same heightened plane. And, to my delight, she had just moved to Clinton Hill, a few blocks from me in Prospect Heights. Our reunion was firmly on the books, and once we finally caught up, I was tickled and stupefied when I learned about her circuitous route to such a prestigious position.
“I’m not a person who plans ahead,” Lindsay admits. “I did no internships. None.” She spent her collegiate summers at a filmmaking camp outside of DC, assuming her bases would be covered. It was how she put her American University film production major to use. Lindsay was humbled to learn that, after her 2009 commencement, she was perfectly unemployable. Dirt broke and lacking any plans, she moved her bed into a friend’s living room, and sectioned it off with a sheet, like in a hospital room. Lindsay grew accustomed to falling asleep as her friend’s roommate watched TV late into the night, and finally came to the conclusion that she would have to move home with her parents—the first in a series of sobering realizations: “I couldn’t find a job, and without a job, I couldn’t afford rent.” So, for the first time since high school, she returned to “the part of Philadelphia that’s in New Jersey” (Washington Township, to be exact). Her life back home fell into a very compromised rhythm: “I have the distinct memory of knowing that there was a second, late-night Happy Hour at TGI Fridays,” she says with laughter, recalling how she frequented the restaurant on weeknights. It was in that Fridays bathroom that she had her next sobering moment: She was examining her singed eyebrows, a sad result of lighting up in the back of a friend’s car as he hit a speed bump. She studied her face in the bathroom mirror while her friends ordered drinks. “I took a cold, hard look at myself, very metaphorically, and thought ‘WHAT ARE YOU DOING HERE?’” It’s almost cringe-worthy, how cliché millennial the whole thing is, like something a Lena Dunham character might do. But Lindsay is ever aware of this, and none too forgiving of her past self, which is why I am instantly in love with my long-lost friend.
Lindsay bolted back to DC, determined to get work and make good. She found a small attic apartment for $500/month in the Van Ness neighborhood. It had no A/C and no heat. It did, however, have a stink bug infestation. “Dozens at a time,” she says. “A friend was over one night and I cried as we peeled like thirty of them off the screen and curtains.” Employers were also peeling her resume out of consideration for various film and writing gigs, and after failing to get any interviews, she once again found herself without any clue for what to do next. “Go figure,” she says now, shaking her head and wondering what that younger version of herself must have been expecting. Then, in October 2009, she got an offer on the spot: with Georgetown Cupcake. As a cupcake clerk. But not the one in Georgetown—the stepsister one in Bethesda, MD. “I couldn’t even get a serving job or a fancy barista job without prior experience, and they were the first place to say yes. I needed money. I had no other choice.” And so, she worked each weekday 10-6, for $10/hour selling $3 confections. Idle time was spent folding boxes—“I could still do this by muscle memory today, I’m sure.”—or making glittery fondant, that weird edible topping that can take the shape of a rabbit or rose or heart. Her colleagues fit one of two molds: other liberal-arts also-rans, and high-achieving high school students whose parents insisted they get a part-time job as a character-building exercise. “You could see the beginning of the millennial dream just crumbling, as they looked at me and the other college graduates. Here, they were stocking up on AP courses preparing for a prescribed life, and my experience was their way of seeing that maybe things won’t go exactly as planned.” Still, she found herself in a mentor role, giving the younger girls advice on who to take to prom or how to get into a good college. That’s as far as her advice could go, really.
Lindsay started writing for the music zine Coke Machine Glow. It was pro bono; the exchange was that she wanted a portfolio, and that they had the platform for publishing her articles. She was already buying these albums and going to the shows, and now she could pair interest with opportunity. She would jot notes and write in the break room at the cupcake shop, hoping the side hustle would lead to something. For the time being, however, she was stuck making fondant, leaving each day covered in glitter and frosting. One afternoon, some television producers came in to meet with her boss, and Lindsay overheard them planning the logistics of a reality TV show about the business—what would become “DC Cupcakes” on TLC. Lindsay connected the dots: a video crew, filming here, at her job…this could be the production gig that validated her private education film degree. She ceased rolling and cutting little carrot fondant shapes, and surreptitiously asked one of the producers if his whole crew had been hired. His response: “Yes, but don’t worry, they’re all really cute guys.” Another sobering moment: she was nothing more than “Cute Cupcake Girl.” She would soon sign a waiver allowing them to include her in the show, when one of her “save-me-from-this-hell” job applications—for an administrative assistant role at AARP—turned into an interview. Her teenage colleague Nina helped her get ready in the back of the shop, coaching Lindsay on her outfit, hair, and talking points. Lindsay left work early for the interview, got the job, and had her one-way ticket out of “DC Cupcakes.” On quitting the role of Cute Cupcake Girl: “It was the best day in a really long time.”
The AARP chapter of Lindsay’s progression is the most interesting, I think. She started as an office assistant and was, of course, unsettled. “But it felt like a respectable thing to tell people I was doing, because I was sitting at a desk with a computer and working for this big, well-known organization.” When a web producer quit unexpectedly, Lindsay was asked to step into the role despite being five years too junior. (Her film production background finally worked for something.) She was assigned to the series “Your Life Calling,” hosted by Jane Pauley, which aired monthly on The TODAY Show. It followed 12 people who, fresh off a mid-life crisis, had reinvented themselves and significantly altered their careers. There was a Broadway dancer who became an acupuncturist and moved into a chicken coop. Another, a lawyer turned chocolatier. “These people on our show, they were miserable for the prime of their lives because they were defining success on something they didn’t believe in their heart,” she says. They were much happier after pursuing whatever synced with their passions and interests, but still pragmatically. It’s why I—and Lindsay, I’m sure—hope that our generation is much happier for the prime of its life. These meanderings and compromises and frustrations that are more common with us often start from a place of entitlement, but they’re sobering, too. And better to be humbled at 25 than at 50. So, after a year at AARP, Lindsay had her biggest realization yet: “I recognized that I was on that path of inaccurately defining my success, too. I didn’t want that to be my life. So, I quit.” She vowed to make ends meet by freelance writing. Considering AARP’s purpose—helping people plan and lead a secure retirement—nobody understood her decision to leave without anything permanent lined up. “These people all hated working there too, but they each thought they had to keep doing it.” To be fair, they were also probably supporting families or nursing tenure. They had something to lose, and being stuck kept all of that preserved.
Lindsay began writing features for the Washington City Paper, and doing reviews for the music site Pitchfork. “I read an article in the Columbia Journalism Review a year ago about ‘the right time to go freelance,’ and they said ‘When you know at least five editors at major publications well enough that they’ll open any pitch email from you.’ I laughed, because that was not at all the case when I went freelance—I just dove right in. I didn’t follow the rules. And yet, looking back, I think that getting in over my head was crucial to succeeding as a freelancer, because it put me in this survivalist, sink-or-swim mindset.” She was tired of sinking further behind her peers who did something practical right out of school, or who had at least derived some pleasure from their day-to-day profession. A visit to New York turned into a little idea that maybe this city could offer her more culturally, and particularly on the music scene. Three months after moving—January 2013 now—Pitchfork offered Lindsay a full time job as Staff Writer. She was finally living one month ahead on her freelance paychecks, and seriously considered declining the role, if only because it might slow her momentum. But, she was rounding 26, and would soon be off of her parents’ health insurance. So she took it, largely for practical reasons. She stayed with Pitchfork until August 2014, having graduated to Associate Editor. New York Mag’s lead music critic Jody Rosen left for the Times earlier that summer, and Lindsay was asked to apply for the vacancy. After enduring numerous intense interviews and writing a slew of “audition articles,” she found herself with a job offer that would make a humiliated, humbled Cute Cupcake Girl very proud. It’s been over a year now, which she counts a feat: “There’s part of me that feels like one year is a really long time. I’ve never made it two years anywhere. When that happens, it will be an achievement because longevity is not something I ever had to value. It never before played into my perception of how my life is going.” And now, the loyalty and practicality matter for something, particularly because she is happy.
I met Buckminster on Scruff—traditionally a gay hookup app, for many a gay dating app—in early 2014. On our first date he disclosed that he’d be returning to grad school in the fall. He was humble about his applications, but knew that he had the pick of whichever architecture program he wanted to attend. In my head, I shouted “Columbia! Pick Columbia!,” so that he wouldn’t have to move, and because I liked him right away. But he was leaning toward Yale, which isn’t far but still two hours by train. Buckminster (not his real name, obviously) was everything I wanted in a significant other: smart, humble, ambitious, charming, handsome, healthy, scruffy. Our first-date chemistry was a synchronized blend of wit, sharing histories, making eyes—all very charged, very jittery. It was that rare, harmonious collision that tells you “This…this is going to be an event.” At risk of growing too attached, I set the countdown timer for his departure in my head, and built a fortress around my heart. Guys like him didn’t come along often, and I wanted to soak him up while I could. After a drink, he walked me to my dinner plans, down Ninth Avenue and into West Village. My buddy was there waiting outside, and I told him to go in and get a table. I wanted to steal a kiss goodnight from Buckminster, and to ask for a second date. I got both.
One thing I adored about Buckminster: he would stop mid-block, on any random street, at any odd hour, and look up to admire a building. He would tell me the architect, the history of the structure, details on the trim or the windows or the foundation, as well as the period in which it was built. He knew the questions I would ask before I knew to ask them. Another thing: he wore dark calf socks with shorts, a style that looked misdirected but that he owned with such confidence, so it worked. I started mimicking him, getting sometimes-curious, sometimes-complimentary comments from colleagues and friends; I’ll never do it as well. He would also wear brightly colored socks under his cuffed work khakis. He was so good with socks. A third thing: he had the best restaurant recommendations, like Bobwhite on Avenue C for dinner, or Eisenberg’s Sandwich Shop for lunch, near both our offices in Flatiron. They always hit the perfect cross-section of New Yorky and Not Pretentious. And he would routinely get food stuck in his beard in an endearing way. Another thing: he was intentional, which is sadly very rare among gay men. For its elusiveness, it is the most attractive quality to me. Buckminster would say what he felt. He would address concerns. He would divulge insecurities. I trusted him wholly from the start.
In my 2.5 years as a New Yorker at this point, I had dated dozens of men—most just once or twice, but three others very meaningfully. For me, “meaningful” meant that they lasted anywhere between two and six months. None of those was ever integrated into my group of friends, however, as I was very cautious about giving anyone the face value until I knew he would stick around, or that I would keep him. Buckminster broke mold, and fast. He always accepted concert invitations, awkward office +1s, or 2 a.m. dancing at Bedlam. And he invited me to parties at his apartment, introduced me to his brother, and showed me around his own office. Like I said, he was intentional, and his actions further expressed his motives. It took me a month, still, to be exclusive with him. I allowed myself to continue seeing other men for a few weeks, but after a couple aimless pursuits, I realized I was taking away from someone who deserved my complete attention, someone I thought about nearly every minute of every day. I wanted to focus all of my energy on him, since he seemed to be giving me his. After all, our togetherness was finite before he would leave the city, before we would yield to unfortunate timing and split ways at the fork just ahead.
One night at Buckminster’s apartment, his close friend introduced me to another as “the boyfriend.” She didn’t think twice of her word choice, but it lingered in my head the rest of the night. We were just two months into dating, and he had only two more in the city before moving to New Haven. We were exclusive—or at least I was to him, and presumed the same of him to me—but I hadn’t once considered any sort of permanence. After all, he was going to be nose-down in books and sketches and projects for the next three years…in New Haven, which is not a charming place, and a haul to get to. And he would be far too busy to get back to New York very often. Plus, I was finally on my feet in the city, with a good job and a solid group of friends. I wanted to be present in the life I had worked hard to earn, to keep, to preserve. I went into things with Buckminster quite protected, but fully excited, because I knew he fit the mold of the partner I wanted. Only now, with an actual title lingering in the air, I felt myself peddling backwards, afraid he might soon use that loaded word, too.
We went to dinner in Williamsburg for his birthday, to a cute New Yorky and Not Pretentious place below the JMZ line that he had suggested. (I forgot the name of the joint in writing this, which irked me since he probably remembers what we both ordered. I tracked down my April 2014 bank statements, saw an ATM withdrawal for the date, and googled the line-item’s address: Café Moto! All better.) After dinner, we walked hand-in-hand up the waterfront and to Baby’s All Right for a Tove Lo concert. She was hardly off the ground back then, and this was her first U.S. show, so she played maybe seven songs. Before the gig, he halted our cutesy, easy talk and, in his intentional way, opened up to me very vulnerably: “I was checked out, ready to go back to school and say goodbye to everything here. But then I met you. And suddenly I don’t want to go. I have to leave, obviously, but I’ve thought a lot about this, and, since I like you a lot and since things are going so well…I think we should be boyfriends. And we’ll make the distance thing work. I’ve thought a lot about it; I know I want to do this.” He said it with such an earnest, heartfelt, warm expression, that it pained me to tell him we should discuss it at another time, since the show was about to begin. My intentions had never been made clear, but now they were emerging. He smiled in humiliation, in shame, in recoil, in hurt. The opening band took the stage: “Ladies and gentlemen, thanks for having us, we are Great Good Fine OK!” What a shitty name. What shitty timing.
It was agreed that Buckminster and I take time apart—a full week—to find common ground. I went to a wedding in Kansas, and was asked numerous times if I had a boyfriend. It seemed too difficult to explain, and unfair to say I was single, so I told them I was seeing Buckminster. A lot of people were very happy for me, equating success with finding a partner, as many in Kansas do. Upon my return, Buckminster and I met to discuss our union. He went first, and had decided that we needed to end things promptly. Go cold turkey. No more contact in any way. It would be the easiest way to move on, he said. I told him I originally thought we could have made it to July, that we could have enjoyed two more months together. But on this night, we found our common ground: my mind was also changed, and I too believed we should cease contact. We embraced one final time in his doorway. A tearful goodbye kiss, a “good luck kiddo,” and a “you too.” I walked very, very slowly down his stairwell, my vision drowned, already missing him, and unsure if I should curse timing or my own stubbornness. At the landing, I found my phone, opened Instagram—the only social network either of us used—and noticed my follower count tick down by one. He had already done the deed, a moment before I was going to do the same. Cold turkey indeed.
“You always sabotage yourself,” says Dan Pelosi (@grossypelosi) of that stifled relationship with Buckminster. “It’s what ruined us, too.” He’s now talking about our own boyfriendship, which started after we met on OKCupid in November 2010. His dating profile was written in his characteristic, self-deprecating humor which I found very endearing. He was 28, and seemed to have a perfect, self-made, well-rounded life in San Francisco. I had gone on a couple dates since moving back to the Bay, but nothing of substance until I met him. I was working at the video rental store at the time, and this was right when I accepted the AmeriCorps job offer to make $9,000 over the next 12 months, so I was certainly a project by most people’s standards. Combined with the facts that I was newly out of the closet and living two stories below my extended family (Uncle Jesse style), I can’t believe he showed any interest at all. After dinner on our first date, we went to a now-closed Marlena’s near his Hayes Valley apartment for drinks and a drag show. That sounds really tacky to me now, but only because most New York drag shows are supremely tacky, whereas San Francisco ones reek of spirit and community. Plus, Dan doesn’t do tacky. Since it was the holidays, there were a thousand Santa Clauses hanging from the ceilings and adorned around the walls. One at a time, a half-dozen queens marched out to lip-synch Top-40 songs and holiday numbers, with dollars being thrown from every which way by smiling, cheerful, not-tacky men and women. When the head queen—Marlena herself, aged 70+—got up to wish everyone happy holidays, she fought back grateful tears and acknowledged the unparalleled, unconditional love in the room. Dan took my hand in his, and squeezed it as a lightness filled my head and then my body. It was the first time I felt like my entire past was behind me, like someone new took my place. Someone with potential. Someone who could learn to be happy. Someone who believed he deserved that for himself.
On our second date, we celebrated Dan’s promotion and raise, which was more than twice my annual AmeriCorps salary. I felt this inferiority wash over me, seeing someone who had compounded five years of real-world work experience so smartly, whereas I had wasted the first two years of mine on being a crossing guard, and watching chickens, and sitting in waiting rooms with idiot models, and working at a video rental store, and now making just four figures. Yet he didn’t seem to care about any of that. “You can equate it to a talent scout, which I know is weird to say,” Dan tells me today, from his West Village apartment. (He moved to New York in 2014.) “I could see the potential. Socially, as our relationship progressed, I could throw you into any situation and never had to worry about you sinking or swimming; you always swam. However, you never saw that in yourself because you felt like I didn’t know who you were, or like you weren’t whatever version of yourself you were most proud of. You had this whole ‘superstar, young Oprah’ persona from college that you claimed was gone, that had been defeated recently, and you allowed it to affect our relationship. And I think you saw in me the thing you wanted to become. I could understand that kind of attraction. It was exciting to you but it also killed us.” We agree that if we had met at the same age—both 24 or 28—we would have had a much longer relationship. “You were at such a different social and economical place than I was,” Dan adds. “And it was like sticking a hot poker into your insecurities. I think the upside of that is that I was able to leave a lasting impression on you in the months we dated. You would take my advice and you still do, but the hard part for me was that I knew, five years later, you were going to be in that same place as me, but it was never going to settle you then.”
So we obviously didn’t last. But between that second date and my psychological dismantling of our union, we really melded our lives together. We went to Austin to meet his best friend and her husband. I met his parents and sister, he met my aunt, uncle, and cousins. My friends from home would visit and, upon leaving, felt sadder to be leaving Dan than they did me. I ate at every notable restaurant in San Francisco, and some in Oakland and Marin, too, because if anything was in good taste, Dan was first to know about it. He called me “Baby Bear” because he convinced me to stop shaving my chest and grow into the proud, self-respecting gay man I needed to be, and because no meal with Dan ended without me having a giant potbelly of food to show off. (And now, like many gay men—and Dan too—I have adopted the bear as my spirit animal.) To this day, Dan is one of the first people I consult for anything, whether it’s restaurant picks, financial advice, dating expertise, or a sartorial opinion. Most of us can think of one person who has had such an impact on us that, in a sliding-door scenario where that person never came along, our life would be almost entirely different. Dan is that for me: He was patient with me when I didn’t deserve it, because he was deserving of someone who could play at his speed, someone who wouldn’t pump the brakes to spare a bruised ego. Where most guys would have lost interest or judged my profession or just wanted to hook up and leave me in the dark, Dan put me in the sun.
We broke up because of Palm Springs. Dan was having his 29th birthday party there, and it was going to cost upwards of $1,000 per person. I couldn’t afford it since each of my paychecks was $400. Dan volunteered to fly me there, to pay for my housing and food, because we were boyfriends and we should be together on his birthday. I said no; I didn’t want to be a financial burden. It was the last straw in a series of smaller, similar moments where I discredited his interest and attraction. I thought it would look bad on me, like he was my sugar daddy who had to tow me along because I was too stupid to get my own life together. I wanted to be around him and learn from him and get all the benefits of dating a cultured, settled man, without any of the social stigmas that might come with it. So, he ended things. “I had expressed that I was completely aware of your vulnerability,” he says. “And thought that my transparent generosity should far outweigh your hesitation.” After we split, though, we didn’t go cold turkey. We continued an on-and-off togetherness for the remainder of my life in San Francisco, which was another six months. It came up a couple more times that maybe we should just be boyfriends again. I enjoyed being less committed, primarily because, when we lost the title, I shed myself of the idea that I belonged to him. My guard came down, and those second six months were much more vivid than the first six. Plus I was moving to New York at the end of 2011, which I decided should prevent us from building anything too serious. However, even after the move, we endured 10 months of long-distance, not-fully-committed connectedness. When I called things off in October 2012, it was because I had met someone I wanted to date seriously. It was unfair for both Dan and me to draw things out while we both searched our own worlds for somebody who could replace the other. I ended it permanently while he was visiting, and I remember watching him saunter away after our final morning together; I felt big enough to go forward without the man who taught me all I knew. His two years of patience, of faith in me, realized. In that moment especially, I didn’t deserve him.
Most people don’t understand why Dan and I remain friends, or why either of us cared so much to get back in touch a few months later so that we could rebuild our relationship platonically. My gay friends are the most understanding of it, though. There’s something ingrained in most gay men, I think, that allows us to herd our exes into a separate category of peers, but a heightened one at that. I remain close with nearly all of my exes—though I use that term generously having only been in two official relationships—as I am grateful for the things each of them taught me and allowed me to experience. I’m not sure how this will affect a significant, long-term relationship in the future, but that man should also be grateful for these ones. They all possess a small part of my history, and while it seems pragmatic to cut someone out of my life when we break up, I strive for a lasting connection, even after a mandated buffer. After all, I chose to invest a lot of thought and care and attention into that person, as he did in me, and I always pick a significant other on that basis: I know he is someone who will continue to impress me for his entire life, because of the dynamic and intelligent decisions he makes. I want to be able to celebrate his wins, even after our chapter has closed. In turn, his support of my endeavors will serve as benchmarks for growth, as if my past lives are converging into the current one. Having that kind of filter on who I date makes everything richer: the conversation, the sex, the quiet moments between the two. Dan sees things the same way: “I was sad for a really long time about us ending things, and I think the sense of loss would be a lot greater if we weren’t communicating still. I don’t get in serious relationships often. It’s rare to find anyone I want to spend that much time with, so any truly significant others will ultimately be in my life forever, unless they do something so horrible to me that I can’t have them around.”
“The playing fields are getting much more even,” says Dan of me, and of why we continue to get along so well. “We can talk about things coming from a similar spot, and that power dynamic that plagued you is gone, partially because we aren’t dating.” Dan lives in a brilliant West Village studio now, which would indicate that the playing fields aren’t really all that even; he’s still master of his craft in the retail design space, pulled to New York by a former boss, and king of his own tightly-knit world here, the same way he was in San Francisco. He’s 33, and I’m 29. I am older than he was when we first met five years ago. That four-year age gap feels a lot less significant, and not just because we’re both older and the ratio of days lived is smaller. I think the bigger reason is that I now frame things with a more settled mind, without concern for where I’ll next move, or what my next job will be, or if I’ll make my own likeminded friends. He can finally ask me for advice, and I can give it from a place of experience, and because I’ve also seen him change so much in these five years and understand his needs. It’s the same reason he can cater his advice to me: our union merely evolved after breakup. “If we had stopped talking,” says Dan, “And I ran into you today, I would be so delighted that you were exactly where I always knew you would be, and that all the things that perhaps sabotaged our relationship and all the things that burdened you—wanting a good job, a great set of friends, the ability to travel—were resolved. Of course, I do get to see this change in you since we hang out all the time. I guess it’s just good to know you’re over those hurdles, and that you feel as comfortable as I do in keeping up our friendship.” I can’t fathom my life without Dan, because I might not have all the things I do—and strong self-worth, above all—had he not been in it.
I have Scruff to thank for most of the men I’ve dated in New York City; Romeo is one of them. I knew who he was before we began speaking in mid-July 2014, which was just a week after Buckminster’s departure from New York. Rather, I didn’t know it was Romeo right away because his photo on the dating app was just a handsome, tanned torso. After saying hello and establishing our flirtatious tone, I asked to see his face. What I got was a face I knew as the ex of my ex. Romeo had dated my ex, Tolliver—a mid-2013 “event”—exactly one year before me. When I dated Tolliver, I always felt like the emotional rebound in a six-month relationship that lasted six months too long. Still, I held a place in my heart and my history for Tolliver, just as I knew he held one for Romeo and for me. “I know who you are,” I wrote to Romeo on Scruff. “I’m Adam. I dated Tolliver after you.” “And I know who you are,” he wrote back. “I’ve seen you on his Instagram. Let’s go for a walk to formally meet? Just because.” It seemed pointless, but also completely harmless. An hour later, I was outside his apartment. An hour later, walking through West Village, looking every direction as if we’d get spotted and hanged, but jiving and laughing like old friends all the while—and flirting a little, too. An hour later, laying casually in the grass of Highline Park well after dark, electricity surging between us. An hour later, back at his apartment, in his bed, keeping our underwear on because we wanted to respect Tolliver—someone I still counted as a friend. (This makes me a very bad friend.) An hour later, on the subway home to Prospect Heights, feeling thrilled, feeling dangerous, feeling bad, but feeling good.
There was no runaround in dating Romeo, no “Are we together or aren’t we?” We just were. I don’t recall ever being anxious about whether or not he liked me or was going to text me, I just knew it was happening and never questioned it. We skipped past courtship, and settled into the vacuum in which we lived for many months. He and I were cursed from the start, though; everywhere we went, I was certain Tolliver would round the corner and bump right into us. We both still cared for him, and knew that he thought highly of each of us. If he found out, it would devastate him, knowing that two very important, emotional parts of his past came together because of that common ground. Romeo and I were both afraid to risk losing that respect from him, too, even though we liked each other enough to start our own unofficial union. We started ordering delivery instead of going out, and would take taxis anywhere we went, to get door to door without risk of awkward run-ins, knowing that Gay New York City is far too small. Only our best friends knew we were together, because Tolliver and his network of friends—which overlapped both of our networks—could be peering out any window or sitting in any restaurant. We kept our Instagram accounts clear of trace, too: no following each other, no posting photos of our joint ventures. That way of documenting romance was forbidden to us. But for these same reasons, we grew close. Every moment was private, was playful, was affectionate, was ours alone. Maybe it wasn’t so cursed after all.
Romeo rented a car and drove us to Connecticut one Saturday afternoon in late summer. We met some of his closest friends for drinks—they were all slightly older, creative-director types like him: owned houses, had families, came from money, or at least made a ton of it now. I felt inferior, given I was a mid-level editor and owned nothing more than a bed and a few nice jackets. I definitely had the best hairline, though. I would certainly NOT be in the same financial wheelhouse as them in the next few years, which made me feel significantly behind them professionally, even if my variables were different, even if my definition of success was already being realized. Romeo saw all of these thoughts unfolding in my head; my quieter demeanor and critical stare must have given me away. Every introduction he made, every conversation he started, he was sure to make me feel equal, to make me feel like I belonged, and that it mattered for nothing that he had money and I did not. I hate that I feel small around people like that. I don’t even want lots of money; I just get uncomfortable because I’ve never had any, and because I make unfair presumptions about people who do, despite the fact that I’ve taken many a handout. After this moment where he introduced me to his friends, I felt understood, and also like the chip on my shoulder was gone, at least around him. Sure, I felt smaller than them, but I also felt deserving of the affection he directed at me—a self-worth test I had failed when dating Dan (@grossypelosi). I loved that weekend, and I loved Romeo that weekend.
During that same weekend in Connecticut, we stopped off the highway at an antique shop. Romeo wanted to browse, hopeful he might find a cool end table or mirror to bring home. I certainly didn’t need anything, seeing as my queen bed took up 90 percent of my bedroom, and my clothes took up the other 10. But then, while he spoke with the owner about a certain piece, something caught my eye: a carved, painted wooden doll, maybe eight inches high. An old woman—a gypsy. Her hair was tucked into a shawl, and she was clutching a bible, smiling. Scribbled m on the bottom was “A.P. 1936.” I turned to the shop owner: “How much for this?” “Uhhh,” he hesitated. “10 bucks?” He stared at me as I stared at her, as if trying to force the sale. My wallet was in the car, so Romeo paid. Back on the road, we named her Heather. It seemed silly enough, and made the eerie idol a bit more innocuous. I set Heather in my windowsill when I got home, and posted an Instagram prompting everyone to say hello to her. A comment, from my friend Ben (@benjaminnyc): “What’s your damage, Heather?” Nothing, yet.
I ran into Tolliver once while all of this was going on. It was near Washington Square Park. We caught up very cordially for a few minutes, and the entire time I thought “I’m sorry. I don’t want to hurt you. He doesn’t want to hurt you. This doesn’t change what he and you had, or what you and I had.” This was one of the few times in my life that I felt like an actual terrible person: being face to face with my ex, feeling like I pulled the ultimate “All About Eve,” only now it was All About Adam, about what I assumed from him. His place in Romeo’s bed. Thoughtful texts. Terrific sex. Romeo had the same guilt, as if he stole me from Tolliver’s memories too. I felt bad for Tolliver, that he was smiling at me, genuinely interested in my goings on, and that he still thought well of me. Then I just felt bad for myself, and for Romeo, for getting ourselves into this predicament, and for not getting out of it on principle alone. But also for being cowards who weren’t willing to give him the momentary grief in order to sustain ourselves. I still wonder if either of us will ever tell Tolliver our secret. I don’t want that truth to alter his memory or opinions. But, before you pity me and Romeo or feel too sorry for Tolliver, trust me here: Romeo and I really were a superb fit, and we can’t help how we met. I often imagine what Tolliver might feel if he found out, since Romeo was his “one who got away.” I think it would be like a sucker punch, doubly so because his heartbreak for Romeo was the sole reason Tolliver and I never got a fair chance when we dated. Or maybe he would think we were despicable, and that we deserved each other. He’d be right, if you asked me.
Since we weren’t public as a couple, Romeo and I were never exclusive. In all the months we dated, we did not vow fidelity, nor did it seem like either of us wanted total commitment to a furtive relationship. But we were committed in some way; we were each other’s first priority, except that the entire time we were both searching for someone more compatible to come along, someone not anchored by guilt or shame. Neither of us made the effort to build toward longevity, to risk having to tell Tolliver. So we continued our weekly cadence of ordering in, having sex before the food arrived, watching a movie while we ate, and passing out promptly thereafter. One morning, as I left his place, I thought to check my Scruff messages, which had been ignored for a week or two, per usual. Then, a text from Romeo: “Two minutes out my door and checking Scruff already?” I was livid: “You had to check yours to even see that I signed in,” I replied. “Plus, it’s 9 in the morning, what do you possibly think I’m looking for?” We both knew the answer, though: Something else.
“We all have a history of falling for people who are unavailable to us,” says TC Milan (@tc_milan). He’s relating to my Romeo-Tolliver love triangle, making me feel not-so shitty. “It’s fucked up in theory, but you never acted out of spite. And at least it’s interesting.” I knew I could count on him for the support. TC is the lead singer of one of my favorite bands, @avanlava, and aside from writing prolific songs and throwing some of the best parties I’ve attended, he gives off a refreshing air that says “be dynamic, or don’t bother.” I first encountered him while visiting DC in 2013. Avan Lava was playing a big Pride party, on the third floor of an old Wonder Bread factory. A thousand men were body to body on the fourth floor to see some Drag Race demi-celebrity, so my friends and I snuck one floor down to check out this band that was unfamiliar to us. We joined a crowd of maybe 200 people who were dancing and spinning to TC’s theatrical voice and the electronica-meets-pop instrumentals. It was the tail end of Avan Lava’s set, right before they launched into their show-stopping “It’s Never Over”; that’s when they always shoot confetti and body surf and rub sweat with the crowd and memorialize the evening. TC and a shirtless Jo Lambert (@jo_equality) came out into the crowd; she jumped into my arms as we twirled around. “Where are you from?” I screamed above TC’s voice. “Crown Heights, Brooklyn,” she yelled back, shaking her tape-covered breasts and locking eyes like she was casting a spell over me. “I’m from Prospect Heights!” I hollered back. “Neighbors!” She planted a kiss on my lips in celebration, then twirled away. I recommended them for a gig nearly one year later—at the concert where I introduced Buckminster to my friends—and befriended TC as we stepped through logistics for the show. That night was memorialized too, as they shot their confetti over the entire crowd, as we danced to TC’s words: “We’ll all be alright // If we stay up all night // Let it feel good // ‘Cause it feels good.” Everything is perfect with TC as MC.
TC got himself in a mum’s-the-word bind recently, too. “I have a tendency to go after straight guys,” he says, expounding on that general pursuit of “unavailable” people. “I’m around a lot of dudes and bros who are music nerds. They’re the type that is open to new experiences.” My eyes are wide as I wait for the details. “This particular guy used to date one of my best girl friends.” I choke on my salad as he laughs to himself. “Yeah…but it was after they broke up. They had been having trouble in the bedroom, which she would tell me all about. So it’s not like I should have been that enamored or curious about him. But he’s really creative. Always working on something, actually creating things for himself and as art, like 24/7. Most people aren’t like that. I’m certainly not like that; if I write a song, it takes a while and then I need a break. But this guy just lived it. I found it really sexy. And after they broke up, he seemed to always be hanging around the studio, lingering after practice, taking photos, smoking pot. Even an occasional back rub. To the common eye, it looked like we were just becoming friends.” I’m giggling like an idiot teenager the entire time. “Oh this is goooooood,” I say as he shakes his head, grinning wide.
“So, this guy was staying two blocks away from me. One night I was hanging out with my ex. We went to dinner then saw a movie, and I assumed we would hook up after. Instead, my ex said ‘So good seeing you, let’s do it again soon.’ I was upset, so I went to my drummer’s house, got drunk and then got a text from my friend’s ex. It said ‘Yo what’s good tonight?’ I replied ‘Drunk, defeated, what’s up with you?’ … ‘Nothing, just gonna chill, smoke. Watch a movie. You should come over.’ So, I hopped in a cab, but when I arrived there was no vibe. I had no idea why I was there. We were talking about absolutely nothing in his bedroom for an hour. I got tired and said I was gonna go. At first he was quiet. Then he just moved to the bed, paused, and said ‘Come here.’ And so…I did. We started making out. Then got naked. Then he said that he had never done anything like this before, which, who knows. But it lasted a few hours. He was asking questions like ‘Should I do it like this? What should I do next?’ He gave me the whole ‘Nobody can know about this’ bit. I was on the same page at first, because I was terrified of telling my friend I had just slept with her ex-boyfriend.” I interject: “Are you sure I can write about this?” “Yeah, I mean, I had to tell her. I care about her, more than I do him. And our group of friends inevitably found out. People know by now, and my friends don’t give a shit. They thought it was awesome that he felt comfortable to do that, and she wasn’t mad because it’s not like they were dating at the time.” “When did you come clean to your friend about it?” “After enough time. Once I was sure she didn’t care about him anymore. If you’re thinking about telling your ex that you dated his significant ex—knowing full well it would hurt him—, well, that information won’t do much good for him for a while. But tell me why you feel so guilty about it anyway? You’re all adults, making your own decisions, and nobody cheated on anyone. The secret seems kind of straining, but after a while it won’t mean anything. I hope you don’t regret losing this Romeo for it.”
TC’s story had me thinking about the “shameful” secrets any one of us carries around, and my mind jumped to 2007: It was the first time I hooked up with a guy. I was 20, a sophomore in college, and had a house in downtown Lawrence, KS. My roommates went to a basketball game so I knew they’d be gone for a while. I invited this stranger over; we had been chatting through the website Adult Friend Finder (ha!). I was excited to finally act out on this secret I had been harboring. This guy was in the closet too, a former military man, 25, super muscled and really boy-next-door. He parked his pickup truck outside my house and came in. We said few words before he was in my bedroom on his knees. We didn’t even kiss, never once exchanged names. He peaked pretty quickly, but I was so nervous that it took me another 20 minutes or so. “I’ve got to hurry into Kansas City,” he said after, while putting his clothes on. “It’s my birthday and my fiancée has been waiting 45 minutes for me at the restaurant already.” He chuckled at the fact, never mind that Kansas City was an hour away. He left, and I felt like a home wrecker. On the one hand, I was happy to have finally acted on my urges, even if it would be another 3.5 years before I came out. On the other hand, though: that poor woman. Even worse, he emailed me the following day saying he wanted to do it again, and, if I was up for it, he could bring me to hang out with this married couple he always had threesomes with. I declined, and deleted that fake email account. I wondered how many people I knew and loved and respected also had terrible, hurtful secrets like this guy. I hate that I still have such anguish over something like my Tolliver-Romeo love triangle, which involved no adultery or dishonesty, while what’s-his-name in Kansas probably has two kids and a dog now with his unassuming wife, fucking college guys off Grindr while she makes up the bed. If he’s still at it, I hope he’s miserable. But more than that, I hope enough time has passed, and that he’s been honest with himself, and with her, and freed of any burden. My trust in people shifted significantly that day. But so did my understanding of them.
“When I was 15, doing Christian theatre, I had a very intimate relationship with one of the instructors, who was in his mid 20s,” TC tells me. “It lasted a year or so. He had a roommate and she was always yelling at him, worried he would go to jail or something.” I sit fascinated at the way he just shares this nonchalantly. And there was another: “When I was 16, I started seeing this 32-year-old man in San Diego,” he tells me. “He directed a show in my hometown, and my best friend and I went to see it. We had fake IDs so we snuck into a gay bar afterwards, and these guys approached us, and they were the director and producer. They started flirting with us, so we lied and told them we were 18 and 19, which still means we would have snuck in. They invited us back to the hotel and we each hooked up with one of them. Then, for like nine months, I would drive down to San Diego, under wraps.” I ask TC what he thinks of this now, the idea that these guys were twice his age and sleeping with a minor. “I think we all knew better, but I very willingly went into both situations,” he replies. “Those relationships were an escape from my family, from any high school drama, and felt like an intriguing passage into adulthood. They were as secretive as my sexuality itself, so I was stoked to explore them. Either way, my being young forced us to be quieter, which kept things very intimate and private. I’m not encouraging relationships with minors, but am just saying that what you and Romeo did probably forced you to realize that you both want something substantial. Even as I have fun stories like hooking up with that straight guy, they just make me more grateful when something natural and long-term comes around. I like a challenge, yes, but I’m really looking for someone who challenges me, not for a good story. It’s fun to have something interesting like that, but more than anything, I want someone I can easily integrate into my life. It’s good to first experience the contrast to that…to know what you actually need for personal betterment.”
“I obviously don’t often get into relationships that are easy,” TC says. “My last boyfriend was getting his PhD while we dated, and had very little time to invest in the relationship. I would ride my bike an hour to his house and we would have dinner just so we could spend time together. I fell for him partially, I think, because it shouldn’t have worked at all. I surprised myself at what I was willing to do. And just like you with the architect, we knew our time was limited because he was going to have to move for his program. So we broke up a year early, to spare that drawn-out goodbye.” I think for a second about the handful of men I would consider my “significants,” whether they had a title or not. They’re the class of men I feel has most impacted me in the last five years of being out. There’s Dan (@grossypelosi); I knew while dating him I’d be leaving San Francisco for NYC. My first boyfriend, in South Dakota, got dumped because I was leaving there for San Francisco. My first NYC love—the one for whom I left Dan—was bound for Amsterdam and emotionally unavailable as he plotted his move. Tolliver was a challenge because he was never over Romeo. Romeo and I were doomed because we didn’t want to hurt Tolliver. Buckminster was moving so I never let my guard down for him. There was also a 48-year-old penthouser who spent most of his time away from the city, and a 21-year-old who lived in Montreal. See a pattern? Nobody who just…made it easy, nor anybody for whom I let my guard down when it made one bit of sense. If you gave me an agreeable, hardworking, handsome, intentional 30-year-old man who is settled in New York with a good job, friends, apartment, and the works, well, I’d probably consider myself unworthy and have a nervous breakdown.
While it’s important to surround yourself with exceptional people and to do fulfilling work, nothing can keep you as grounded as having a home that you love. This is the cardinal rule for surviving NYC, too; the days and people and cost are so unforgiving, that having a sanctuary to which you can retreat, relax, and rejuvenate should be every person’s top priority. When I moved here, I knew I would probably end up in Brooklyn; most of my friends suggested I try Williamsburg. I looked at a half-dozen terrible, not-worth-the-cost arrangements there, when my ex Dan (@grossypelosi)—always looking out for me—asked for leads from his friends. His high school pal replied that she had an opening in her rent-stabilized, $750/month Prospect Heights 3-bedroom. I hustled to the 2/3 train later that night, and took it for 30 minutes into foreign territory. I popped out in the crisp January evening, with no clue as to where I was, but humbled by the very first thing I saw: the majestically lit Brooklyn Museum. I walked down Eastern Parkway, which, with the enormous Soldiers’ and Sailors’ Arch at one end, feels like Champs-Élysées minus any commercialism. There’s also Prospect Park, the Brooklyn Library, and Botanic Garden all on one side, across from a never-ending row of stunning pre-war apartments. “Do people in Manhattan realize this is here?” I wondered, already enamored—and even before I discovered the brownstones, charming restaurants, buzzing pubs, and quiet coffee shops. The room was in a row-house building, a first-floor unit. It was in the very back of the apartment, removed from any noise and with a large window that opened into the private backyard—which was only accessible through this space. It was a small room, big enough for a bed and a shelf, but at this point I only had three bags of belongings. I knew I needed this place, no hesitations. I charmed my potential roommates—two witty, intellectual best friends—over wine, and got a phone call an hour later with an invitation to move in. I knew this apartment would finally keep me anchored, and that Prospect Heights would be the foundation for the fruitful years ahead.
The more stories I heard about other people’s housing misfortunes—from bad roommates to stubborn landlords, from bug infestations to rent hikes—the more I realized how lucky I was to have landed where I did. Many of my friends were paying twice as much as me to have even less space in noisy corners of Manhattan, a tradeoff that seemed entirely illogical. Not only did they have to pay way more, but they didn’t have quiet nights and weekends, nor did they have pristine, enormous Prospect Park just minutes from their stoop. It had all the perks of Central Park—even the same architects—minus any touristy gimmicks like pedicabs and horse-drawn carriages and street performers. My commute was 30 minutes, which is probably the average for most New Yorkers, even those living in lower Manhattan, and after any long work day, the stress melted away as soon as my eye caught the Prospect Heights brownstones. I had the best setup of nearly everyone my age, or at least those who had to earn their own keep and pay their own bills. For three years I stayed there, tolerating minor things like fussy radiators and occasional mice in the kitchen—nothing was so bad that I ever thought of leaving, especially for the price I paid. However, when my close friend Daniel (@danielseunglee) had a bedroom open up in his apartment in Crown Heights in November 2014, I decided to gamble my sanctuary and move slightly east. It was just $100 more for twice as much space, which was timely since my tiny room was now brimming with accumulated belongings. This new place was a third-floor walkup, still rent-stabilized, still a row-house, and still back-of-house, away from any noise. Plus, I’d have only one roommate, who was also a best friend. It all made perfect sense, like I’d be trading the old haven for new. I had it good, but I still thought I could do better, so, I rolled the dice and cut myself free of that three-year anchor.
My move took place a few weeks after I got that wooden gypsy idol, Heather, from a roadside antique shop. I set her up on the desk in my new room—I had space for a desk!—alongside various trinkets and candles and whatnot, and just below a framed drawing of a friendly, burly bear. My room came together very quickly, as I didn’t want to waste time settling in and calling it home. One morning in early December, I woke to the sound of a man screaming bloody murder, and I jolted upright just as the framed bear illustration leapt off the wall and shattered onto my desk. I jumped from my bed and tiptoed carefully to examine the scene, and there, underneath the face-down bear and broken glass, was Heather. Nothing else on the desk had been affected by the fall, despite the fact that she was neighbored by other objects; the bear somehow came off its mount and leapt atop her. I tried making sense of it, wondering what could have possibly caused this. And what of the man screaming in agony? I picked up Heather and examined her closely again. No tarnishes. She stared back, smiling and clutching her bible. I felt goosebumps everywhere. All of this happened in the span of 30 seconds, and then, to make matters even more curious, my alarm went off while I clutched her in my hands. I had been setting the buzzer for 7:09 a.m. each day, since July 9 was the day I met and fell for Romeo. So on this morning, everything had happened at 7:08, waking me just moments before my assigned 7:09: a scream, a leap, a crash, an alarm.
Daniel and I smudged the apartment with sage, cleansing each room with smoke to ward away any bad spirits that Heather carried with her. Daniel believes in ghosts and the supernatural, and he worried about what sort of curse I had brought to the apartment. I found it a little silly, but played along because whatever had happened in my bedroom was disconcerting. Romeo was unsettled by it too, but pointed out that the black bear must have played some part in protecting me. I really loved Heather though; she was unique, a memento on my desk, a reminder of Romeo. I refused to actually rid of her, and picked her up that next night, while the sage still lingered in the air, to tell her this: “Whatever baggage you’ve got, it ends with me. I’m going to win this one.” It was a challenge, really, and maybe an acknowledgment that I believed in the supernatural, too. Try me, old woman; nothing can shake me. I’ve been weak, and I’m not going back. I positioned her where she stood before, as if to prove to this silly doll that I had order. I re-framed the bear drawing the same day, and hung it above her again. She had a new neighbor, too: a small black bear figurine that Romeo bought for me, to look over her shoulder and keep me safe. I think Romeo felt some guilt, as if our togetherness created some sort of bad juju: “This bear is for your peace of mind, bub. Or maybe mine.”
I harassed the landlord daily to get us a new lease, one with my name on it that I could sign, one that fixed me to the stabilized rent and that would keep me there just as long as I had been in Prospect Heights. The tenants below us had recently moved out, which allowed him to hike the rent on the new guys moving in. Given the increasing popularity of the neighborhood, I understood why he didn’t want my name on the lease, why he hoped we would also leave. So, I bugged him regularly, hoping that the nagging would have him finally deliver the document he owed us. Soon, I had a second complaint, too: Our top-floor unit housed the release valves of the building’s heat pipes, which steamed out into our kitchen and bathroom. It wasn’t just hot air, though; it also exhausted a pungent, sulfur-meets-burnt-plastic smell. I dreaded going home every day, since my stomach would turn over the second I walked in the door. I would get takeout to avoid using the kitchen, and would sprint to my bedroom to eat it. Showers were short, and I would have to breathe through my mouth to avoid feeling uneasy. Daniel’s sense of smell must be compromised, because it only added to my angst that he didn’t find any harm in the matter; I must be crazy. Paranoid, I suspected foul play from the landlord, like maybe this was some old building owner’s trick for smoking out unwanted tenants. Perhaps I was just getting what I was paying for; I assumed the smell would eventually wear. At least I still had my room, which was free of pipes and instead heated by a radiator that I could control. I didn’t have to worry, so long as I had that reprieve. So long as I had some control.
One morning in mid-January 2015, I woke to the radiator spilling hot water; in a few minutes it had already lost a half-gallon. I was used to this happening a few times each winter at my old Prospect Heights abode, and knew how to bleed the pipes in order to get the steam flowing through. I received a text later that day from the landlord: the water had leaked into the apartment below mine, where the new tenants were living (and paying much more). He asked me to leave a key under the mat so he could examine the radiator while I was at work. I obliged, asking him to please bring a new lease (as I had been requesting) and to finally address the stench (as I had been requesting). He agreed to handle both. I returned home that night to the familiar rancid smell, and found exactly zero leases. Furious, I hurried to my bedroom and slammed the door, only something was different about my sanctuary: it was hot…boiling hot, in fact. The radiator was on full blast, and I could feel the searing metal from across the room. I tried turning it off, only now it was locked on. I texted the landlord: “What did you do to my radiator? Why is it locked? And where is the lease? And did you even look at the pipes to fix the stench?” His response: “Is the radiator leaking?” Now I was boiling: “No, you seemed to have fixed that. Congratufuckinglations.” Then him again: “If it’s not leaking, then there is no issue.” I screamed when I saw that text. I was livid, but could do nothing. I plugged in the air conditioner, which had a built-in temperature gauge. It said that my room was 116 degrees Fahrenheit (roughly 47 degrees Celsius), and the cold air it generated was doing little to combat the internal heat source. I felt even more helpless now. There was a pit in my stomach, a desperation I had not felt in over five years, ever since that panic attack in San Francisco. This was supposed to be my home, my sanctuary.
My cousin Jenny Christen (@approximately) arrived in New York just three weeks after me; she initially moved for an unpaid design internship to round out her fine arts degree, and nearly backed out, but bought a one-way ticket that would force her to uproot every security in Moorhead, Minnesota: the academic bubble, a new car, a cheap rental home, a boyfriend who loved her. When she landed at LaGuardia late on January 3, 2012, Jenny took her 38-lb. suitcase (“I remember that because I had gone to the airport the night before, nervous that it would be over the 50-lb. limit.”) and gave the cabbie her Brooklyn cross streets. Of all the Craigslist outreach she did to find an apartment in New York, this was the only listing for which she got a reply. All she had seen was one photo with a brief description of the 98-square-foot Prospect Heights room, but at $650/month, it was one of the few affordable options, too. “The photo showed some sunlight coming in,” Jenny says. “It looked so quaint, so I kept going back to it. I followed up over and over, badgering her, and when the woman picked me, she said I seem led like I really needed it.” Jenny grew fearful as the car crept south through each pitch-black neighborhood. She wondered where it would stop, when the driver would deliver her to her new home, her new life, and a lot of uncertainty. For a starry-eyed 23-year-old from Minot, North Dakota, it was terrifying to pass abandoned warehouses, police cars on every fifth corner, and to be dropped on a snowy stoop in what felt like the middle of nowhere. The woman from the emails was there, and let Jenny upstairs to pass off the keys. She left behind two towels and a tiny child’s bed. “My feet hung over the end,” says Jenny, who is all of 5’1″. The room was cold, so Jenny put on her coat, pulled a towel over herself like a blanket, and tried to fall asleep. “I was trying not to freak myself out,” she laughs. “I knew that if things were bad the next day, I could be skeptical, but because she left me a bed and towels, at least I had something for the first night. At least I could start with that.” And hopefully, come morning, a sliver of sunlight, as advertised.
In the morning, Jenny woke and mapped the nearest grocery store. She walked outside, passed row houses and brownstones—okay, Brooklyn, not so bad—and found charm on that gritty January day. A Jamaican man catcalled to her: “Hey, pretty lady, you wanna have some zebra babies?” Okay, Brooklyn, you’re luckily unlike Minnesota or North Dakota, and that was a funny reminder. At the store, she bought a loaf of Wonder Bread and a jar of peanut butter: “That’s what I ate for all three meals for the next week. I had quit my college-student job, and moved with hardly any savings. I had an unpaid internship and put half of my money toward my first month’s rent, so….” She came into Manhattan that night—I was couch surfing in Alphabet City—and we met near my offices in Flatiron for a Thai comfort dinner, to toast to our new life sans Wonder Bread. Jenny described her place, sounding tepid but optimistic, and recounted her night on the child’s bed wrapped in a towel for warmth. I’ve known this darling woman for her entire life, and after our road trip across Canada and down into San Francisco two summers prior—where we spent the season acclimating to life outside Dakota, where I saw her smile wider than I thought she was capable, before she went warily back home to finish college for another 18 months—I worried she might never allow herself that added meandering to New York, that leap of fear and faith and weightlessness. But here she was, with next to nothing in her name, freezing cold, completely broke, and terrified, slurping coconut soup and trying to stay calm but seeming, above all, freed. What a blessing to have my cousin here, sharing this transition. Even better, when I snagged my own Prospect Heights apartment two weeks later, it was, coincidentally, on the opposite corner of the same block (thus making her “Jenny from the block”). Both of our mothers breathed a sigh of relief when they got that news. Jenny helped me pick out shale gray paint for my bedroom walls, and together we blanketed the space in its new color, manifesting a prosperous, hard-earned life.
Jenny’s and my aunt Amy (@amycleonard) graduated from Minot State University in North Dakota in 1986, the year I was born. Armed with a business degree, she has worked in the sourcing side of retail, holding VP and SVP roles at Gap, J. Jill, Levi’s, JCPenney, and Banana Republic, traveling around the world to farms and production factories. To a lot of hard-working people, this probably seems par for the course—move to a big city, land a job with one global name, put in the labor, get promoted—but from my roost in Sioux Falls, and from Jenny’s in Minot, Amy was remarkable. She broke mold. I couldn’t believe she did all of that, given my small scope on things, given that she started as humbly as I. Not to mention, she married a charming photographer, has three brilliant, wisecracking children, two senile wiener dogs, and bought a four-story building in San Francisco’s Russian Hill (with a vacant loft for transient nieces and nephews). She got the worldly version of that small-town ideal. In Sioux Falls, there’s a big advertising campaign called “Stay Close, Go Far” that encourages high school and college students to invest themselves in local industry. Jenny saw this kind of “stay local” propaganda too, especially in Moorhead, MN, where she attended college: “Most people wouldn’t leave the Fargo-Moorhead area,” she says. “Everyone talked about Minneapolis as ‘the big city’ since it was close enough to home, and since there were big enough jobs and industries there. It seems good enough, and safe enough.” Close enough, big enough, good enough, safe enough. I understand that we’re all wired differently, but let’s paint a scene: Amy and Jenny and me, backdropped by the smoggy city skyline, pointing to it, beckoning them to join us. Our jaws are agape that hundreds of our classmates point to the blue-skied suburbs of Minnesota and Dakotas behind them, shrugging like “Why risk it?” Our response, as we turn our backs and walk toward the metropolis, eyes on the skyline, on the dynamics: “Risk what?”
For Jenny and me, Amy was the torchbearer for this idea that maybe our frustrations with the way people accept a fate of…homogeneity, of guilt for leaving their families to start a selfish life, of staying local and letting their opinions go unchallenged and curiosities go starved, of using religion as a crutch for interpreting the nuances of the world, of not experiencing contrast before committing to something like love or vocation or location…maybe those frustrations could be escaped. I think Jenny and I both felt like we didn’t deserve the life Amy gave us when she opened that loft to us. She could have rented it for a few thousand dollars a month; there’s this California-king bed nestled on the landing, ceiling-high windows (the ceiling is two stories high) overlooking the entire San Francisco Bay and Alcatraz, all right off a private backyard nook. When we put our bags down in that room and were told that the city was ours to discover and explore, and that we could bring boys home and have parties and treat this loft like it was privately our own, so get out there and have some fucking fun and make mistakes and be grateful but don’t be so polite about it…it was easy to feel like we weren’t worthy of all that had suddenly been handed to us on our respective occasions. Amy worked at our self-esteem to show us that we were deserving, and that the expectations we had for ourselves could be reset to this new open-minded, aspirational world. Here was a taste, for however long we needed our hands held. And then, like our parents, she expected us to cut ties and work for it ourselves. Because we were still Midwesterners, and always would be.
After a few months in her Prospect Heights apartment, Jenny graduated to the next-biggest room, when one of her three roommates moved out. It allowed her to upgrade to a full-size bed, get a tiny desk, and rediscover the perks of closet storage. A small victory, but one made possible by other successes: having consistent graphic design work, feeling anchored in Brooklyn, loving her roommates who felt like sisters. The small graduation was really an affirmation, a confident settling. We still had to earn our New York stripes, but I got to see my anxious cousin blossom; that nervous girl I greeted in January just a half year before…she was gone. Jenny attributes her peace of mind to the initial paring down she did to first get herself here: “I learned to live with less. Learned to feel lighter. I had so many things I saved, and it was a way of stashing things I didn’t have any feelings for. And so I trimmed the fat. There was nowhere to hide those accumulated things; it was all about owning less, about only having things with purpose, things that you love because you have to consider their worth, and how they fit into the small sanctuary that you are so proud to call your own.” What I love about this mentality is that, while she refers directly to the lack of storage space and frivolous belongings, it also applies to the more conservative lifestyle one must lead to feel calmed: You cannot hide your insecurities behind expensive clothes, overpriced dinners, or monogrammed handbags; anyone who finds interest or intrigue in those things interprets status (or perceived status) as success. Really, you are only successful if you are proud of yourself, if you have to earn something, and if you have to defend it every single day—even if it’s intangible. Most people would look at my or Jenny’s life and find us unremarkable, average. But to each other: potential, actively being realized.
Jenny shares an anecdote about her brown-stoned Prospect Heights street: “A few months ago I was walking by my apartment and there were a bunch of skateboarders. As they passed me, one turned to his buddy and said ‘This is a really nice street.’ They skated away, and his comment made me turn around and really admire it all. I noticed the colors of the trees and the homes, the serenity. It made me realize how far I’ve come in the four years I’ve been here. I was so proud of this place, and of myself. Then my boyfriend told me that the skateboarder’s comment was probably in regards to the actual pavement, since it is quite literally a nice street. It’s very smooth. But, I can appreciate that too….It’s like when you’re in love with someone and it’s been a while since you last felt intensely passionate, then one thing happens that affirms that love, like “THIS is why I’m doing it. THIS is why I love you.” She says this having now graduated to the largest room in the apartment, resultant of anchoring herself, of outlasting her roommates, of taking command of her home and picking her new sisterly housemates, of preserving the sanctuary she has built. And, with the bigger room comes the chance to gather even more thoughtful pieces: a beautiful antique dresser, an armchair, numerous plants, a few rugs, plus a headboard that we found on the curb, which, within two hours, she had repainted and installed to the back of her bed frame, after first sawing off the one it replaced, and entirely by herself. Little 5’1″ Jenny, determined as ever. Remarkable, if you ask me.
At our Birchbox editorial team meetings, we go around the room before getting to any business, and each person shares a “smile”: it has to be good news or something that he or she is excited about. “My smile…is that I paid off my credit card debt for the first time since opening both accounts when I moved here,” I told the team in January 2015. That got plenty of oohs and ahhs, and a few people expressed that they, too, would use their tax return and bonus check to pay off debts. I had moved to New York in December 2011 with $1k in the bank, but it was really my Visa that got me stationed: I had to purchase furniture, winter outerwear, nicer work clothes, monthly transit passes, expensive groceries, even more expensive takeout, even more expensive alcohol….That was all on salaries of $29k, $22k, and $39k for the first year and a half, so my Visa was soon joined by an AmEx, and my debt rose as high as $10k while maintaining just $1k in savings. Never mind that my student loans were still piled high; those would be much more manageable without the $800 monthly payments toward credit. When I paid off both of those cards in early 2015, I felt very adult. Like this new version of me had arrived—the one I knew would clean up the mess of Adams past, the one who finally had control, despite still only having $1k in the bank.
That same month, I noticed a cramp in my stomach. It got more painful as I ate, and persisted for a few days, growing heavier and heavier. My appetite all but disappeared, because food would go in, and nothing would come out. I was uncomfortable doing anything: walking, sitting, sleeping—it all hurt. Soon, I had a series of doctor appointments, as one generalist would refer me to a specialist who would refer me to a separate specialist who would refer me to another specialist who would have no answers. Unfortunately for me, I had just gambled on my deductible at work, following a very healthy 2014, and within the first few weeks of 2015, accrued nearly $3000 in medical bills, prescriptions, and co-pays, all after insurance. I hated that I also had to decide which credit card to put it on: the Visa with lower interest rates, or the AmEx with better mileage perks. The AmEx won, because I was planning a trip to San Francisco. The month ended with a colonoscopy—at my ripe age of 28—and the doctor found nothing wrong. Nothing. “I think you body’s just being weird,” he said. “I’m sure this will pass in a few more weeks. Just drink lots of water, get plenty of fiber, and eat green vegetables, ok?” I wanted a refund. I got charged $800 after insurance for that procedure, and my solution was vegetables? Sure enough, the pain dissolved a couple days later—I had eaten few vegetables—and my doctor laughed at “the crazy things the body can do.” For a few minutes, I thought of all the stuff I could have bought with the $3000 I paid doctors, all for nothing. Then I realized: That money never existed in the first place. It’s just a fake number, a constant debt, one that always reminds me of my limitations.
Winter wasn’t all bad, though. I was getting settled into my new home in Fort Greene, content with the much higher rent since I again had a home that I loved; the extra hundreds of dollars was worth my sanity, even if it put me further into debt each month. A very handsome, very charming distraction came my way, too: let’s call him Cold Hands. We had weekly dates, and it seemed that each one was plagued by a blizzard. We’d be sprinting through the freezing wind and snow, from a bar to a restaurant to a theater, and the dummy would never wear gloves. He’d have to run with his hands tucked away, wobbling like a penguin as he sprinted for warmth. Cold Hands overlapped my dating Romeo, so now at least two nights each week were filled with dates, and I was doubly enamored. Where Cold Hands won out, though, was that I saw myself mixing in with his friends, and he with mine. On top of that, he let me take him on dates to Whole Foods, where I could pick at the salad bar and bland chicken, in accordance with the doctor-prescribed diet that I had to follow. (No restaurant would offer anything so plain.) My weird diet endeared me to him, and his indifference to it endeared him to me. The entire month was sexless, too, with both men, since I was so agonized by stomach cramps. It further endeared Cold Hands to me that he respected this compromise , though not without a friendly joke or two; I kept a good humor about it, too. Most importantly, our worlds felt even-planed, and it was a much more public courtship than I could ever have with Romeo; it felt full of potential, reminiscent of a certain architect I let slip away. I decided I would finally end things with Romeo, and instead invest in what I knew was worth my time and energy.
My symptoms were still plaguing me one night as Cold Hands and I watched a movie in his apartment. I didn’t much feel like having sex, but it seemed inevitable given the location of our date. Luckily, because of his predilection, it mattered for nothing that I had a stomach ache. So, after an hour of foreplay in the living room, we consecrated things in the bedroom, then finished our movie before staging a sequel. I left his apartment enamored, and our communication in the days following cemented the fact that I needed to break up with Romeo. So, I called a summit, and went to Romeo’s apartment a couple nights later for what we both knew was our last hurrah. We ordered dinner, and had our talk while we waited for the food to arrive. It was the single nicest breakup I will ever experience: We professed our love for each other, admitted that we could never get to higher ground despite that fact, anchored by our own guilt. We had both been dating around for the seven months of our togetherness, and promised to stay friends, to remain very close, to support one another in our separateness. Lucky for me, my symptoms had dissolved in the days following sex with Cold Hands—maybe he had magic hands, too—because my predilection with Romeo required a healthier disposition. The food arrived, but we set it aside to fully appreciate each other one last time. In the morning, he skirted away early for a flight. I woke alone in his apartment, and stole a final glance at every angle of the place, taking mental photos and a few actual ones; I wanted to have it all in my memories. I soaked up his scent, studied his adorned walls, kept the sticky note he left on the espresso machine (“All set for you bub. Just push. xx”). After cleaning up, I latched the door and escaped to work, grateful for our union, but imagining another.
A late-January blizzard kept much of New York indoors. I texted Cold Hands to see that he was safe and sound, worried mostly for his fingertips. He was indeed fine, but was also nursing a fever. He confirmed my own refuge, then signed off for the night so that he could sleep away the ailment. While cleaning, I found a pair of extra gloves in my apartment, and thought it would be cute to give those to him on our next meeting. The following morning, I checked in again, to see how he was feeling. I never got a response. Initially, I thought maybe he was actually very sick, certain he wouldn’t just drop interest so suddenly. However, Instagram confirmed that he was alive, as he was posting photos with friends and looking healthy as ever. I wanted a refund on my expensed energy, and I wanted Romeo back, too. I would get neither. I also wanted an explanation, but had been down this road plenty of times—on both sides of it, too—and knew I wouldn’t change his mind, and that there might be no explanation at all. These things often end after sex, after all mystery is removed. I chalked it up to him losing interest, to dating other people and being through with me. Even then, I mailed the gloves to his office, with a note: “You need to take care of your hands, kiddo. xx” I didn’t sign the letter; he’d know it was from me what with all the grief I gave him over his exposed mitts. Part of me hoped those gloves gave him some grief over his cold feet, too. Then, a text from him upon receipt: “You sent me gloves! That’s so sweet. Thank you!” I responded politely—“You’re welcome. You really should be more careful with yourself…”—hoping the cold-hearted subtext came through: “…and with others.”
I coasted through February and March with no substantial pursuits—light fare only, open to more, but not needing it—somewhat defeated by the Cold Hands conclusion. I also wanted to save money by not going on as many dates, and hoped to spend more time at home, more time cooking, more time writing, more time at the gym, less time wondering how I’d make it to the next paycheck without over-drafting three days after payday. I got home early one night in early April, lit a couple candles in my room to send some calm into the air, then went to the kitchen to make dinner. I returned to my bedroom with plate in hand, and noticed the candle had been snuffed out, despite it being fairly new. At first it didn’t phase me, but when I grabbed the lighter to reignite the wick, I caught the wooden gypsy Heather’s gaze from her perch beside the candle. “Are you responsible for this?” I asked her aloud. “Very funny. You’ll recall that I’m in charge around here.” I lit the candle again, and faced her toward the flame, just to prove my point. The next morning, I woke up with a walnut-sized welt on my left shoulder. It itched like a hive, and throbbed all morning, before being joined by two others on my right hand and elbow. “Terrific,” I thought to myself at work. “Now I’m allergic to something and I have no clue what.” I decided not to involve doctors just yet, seeing as I didn’t want to waste more money on their supposed expertise. “This will subside,” I convinced myself each day, as more and more bumps began to appear. “I’m totally in control. I have complete control and this will subside.”
One mid-March night, my Fort Greene roommate Shannon Byrne (@shannonleebyrne) returned home late and gasped as she opened a letter from our stack of mail. It was past midnight, and we both looked defeated by our respective days. Next to my computer in the living room were two opened bills, totaling nearly $500 from two minor doctor visits (a small portion of the final tally, you’ll recall). Shannon’s news was worse than my own: She owed nearly $6,000 in taxes and fees before the April 15 filing deadline just a few weeks away. I assumed it was another unexpected cost associated with her music startup A Song A Day (@asongaday.co), which delivers daily song recommendations for dozens of genres—”from humans, not robots.” However, it was a tax return from a job she had held the previous year. “I was a 1099 independent contractor working full time for a French company,” she explains. “They hadn’t incorporated in the U.S. yet, and I didn’t save enough money or plan well. I’ve been doing my own taxes since I was 21, and lately spending too much on my New York life, and didn’t realize I was going to have to owe that much so quickly.” She shook her head as she read the details of the notice, unsure of how she’d come up with the money, but sure of something else: She would figure it out. If anything, when you’re struggling to get off the ground, you get good at avoiding that final six-foot descent into your own grave.
Shannon launched A Song A Day a few months before we met. She cites its birthday as October 21, 2014, the day it first popped into her head. “It started as an idea while I was on a run, which is funny because the demand of operating it has since prevented me from having any time to run,” she laughs over brunch in Prospect Heights. We’re speaking just after @asongaday.co’s first birthday, for which she held a party that doubled as a fundraiser: The startup’s Kickstarter was in its final week, and needed more than half of its $25,000 ask in order for Shannon to receive any (and all) of the money. On why she had the idea for ASAD: “My friends knew me as the music lover, and would ask me how I found new songs and artists. It was such a routine thing for me. After sharing lots of my secrets with them, I realized on that run that they were all too busy to hunt for the songs themselves and just wanted me to hand them over, but not in some algorithm-style way. They liked the personalization. So I got home and bought the domain, then started laying out the site. I sent the link to a few friends who for some reason were also awake, and they all tweeted about it. A few people with high-quality tech networks re-tweeted it, and the next day it was featured on the site Product Hunt, which showcases the most innovative new efforts in tech.” One day, A Song A Day didn’t exist. The next day—and the next year—it controlled Shannon’s life, bringing her the highest highs and lowest lows.
Just before our catch-up brunch, I got an email from the A Song A Day Kickstarter: Shannon would be hosting a telethon each of those final three nights to try and make up the $15,000 deficit. That was very like Shannon, to fill every pocket of her free time with @asongaday.co, right up until the last minute, and to send off an email seconds before I arrived at the restaurant. I was glad to take her offline for a couple hours, even though I knew she wanted to be emailing editors and friends. The campaign had a strong launch: It was featured on Kickstarter’s music vertical, and more than 300 people contributed. It overwhelmed Shannon, who had spent nearly eight months planning the precise details of the fundraiser, down to when it should launch, how to reward donors, what the video pitch should say, and exactly how much to ask for (fundraisers can set their goal, but that target must be met entirely). At our catch-up brunch, I ask how she is planning to make up the difference, in the event that the campaign wouldn’t receive its full amount. A lot of my friends had launched their own Kickstarters, and many of them had an angel donor waiting in the wing, to make up the difference with a personal loan (and only sometimes did mommy and daddy want it paid back). “I have no fallback,” Shannon replies. “Friends are volunteering to cash out their stocks at work, but I’ll never let them do that for me. I might just move the campaign over to Indiegogo.” (That’s a crowdfunding site that doesn’t set ceilings and pays out whatever you receive, which then also prevents you from setting and clearing ambitious goals.) “If I do that, I’ll lose most of the original donors, but I’ll still end up with a few thousand dollars, which will help. People have come out of the woodwork this week to tell me things they did to get their Kickstarter funded, and they’re not things I’m ok doing. It feels a bit dishonest. I’d rather fail in funding than do something unethical. And maybe that makes them better businesspeople than me, and more successful than I will ever be.”
Above all else, Shannon wants A Song A Day to be a large community of music lovers. She wants conversation about songs and artists, running dialogues where people can share their love or hate or indifference about something they’ve been recommended. She currently sends automated emails every weekday to her thousands of subscribers, each of whom is assigned to a genre that fits their taste. She has 44 curators, including herself, and 500 more people who have volunteered to be one. (I’m the curator of the Dance Pop playlist, I’ll have you know. I derive so much happiness from sharing five of my most recent favorites to this pool of strangers, and to have them respond to my emails with rousing support or bitter—albeit friendly—disgust.) But building that community, which includes managing the conversations and all of the automations, takes tons of time. Two of Shannon’s best friends, Danielle (@danifleisch) and Maria (@bhimtastic) have been by her side since Day 1, and have sacrificed their own nights and weekends for a project they feel strongly about, and quite selflessly to support the honest efforts of their pal. Every weekend, the three women would be churning away in our living room, scheduling and responding to emails, fixing bugs, assigning subscribers to playlists, and planning the eventual fundraiser. “They’ve taken on a lot of work,” Shannon says. “It’s nice to have people in the trenches with me, with whom I can talk about it. They’re both such good advocates for the brand. It really keeps me going. They also know when to make me stop and take breaks. They make me live my life. If they weren’t there, it’d be hard. I need those people to talk to. I would be less motivated to keep going, especially now. Having their emotional support is far more important than making money. But I think we all agree that the money would be nice.”
Shannon seems certain that she won’t get the $25,000 funding, but I remind her that she has still filled her entire week’s slate—on top of a part-time job—with efforts to get there. She can’t help but state her regret, though: “I wish I had only asked for $10K or $15K. But I was certain I could get to $25K, too.” A Song A Day doesn’t die if the funding doesn’t come through, but it is significantly hindered from growing: “This money would buy us time. It would allow me to explore a more sustainable model for the business, and to get it monetized. There are steps that need to happen in order for us to get there, like streamline the admin stuff. I need that to be able to approach sponsors. And going out and selling the product would take time. I also want to build a curator database. I want a curator spending 10 minutes at most, and for those emails to arrive in each subscriber’s inbox at the time that is best for him or her.” So, most of that money would be Shannon’s livable income—allowing her to pay her own bills, as well as the various costs that @asongaday.co throws her way, like registering the LLC, hiring consultants, and talking to lawyers—while she builds the community between curators and recipients. Another regret: “I wish I had a mentor. It’s not too late, but I really need a businessperson or someone in the music industry giving me advice, calming me down or pointing me in the right direction. Someone to help me filter all of the unsolicited feedback I get from everyone else, and to save me from impostor syndrome.” I ask her to explain that last part—impostor syndrome. “It’s when you feel like you don’t deserve the attention, or the leadership on something. Like, how did I get here? Why am I the one calling the shots? Why are thousands of people using this thing that I created? Am I doing a good job, or at least doing my best? Do they know I’m a fake?”
“Getting bed bugs when we did…that affected me in the worst way possible,” Shannon says. “It stretched me so thin. I work from home. I was fortunate to be going out of town a few times when it happened, but I just didn’t have time to deal with it, to make it better. I also didn’t have time to move out nor the money to afford it.” For all three of us in that Vanderbilt Avenue apartment, cost was the first concern when the bugs showed up. Dry-cleaning expenses, replacement furniture and bed sheets and pillows and clothing. Not to mention the mental cost: the dread of going home each night, the fear of falling asleep, the disbelief that any poison will effectively rid of the pests forever. The existential crisis that ensues: Why do we live in this dirty city? Why do we tolerate this shit for such high cost of living? “I even messaged my brother in Florida,” Shannon admits. “Wondering if I should move home for a bit to save money. It’s so expensive and hard to get off the pavement here. The cost of moving home—of sacrificing opportunity—however, or of leaving New York in general, is too great. I can have so many meetings here within the industry, and go to every concert I want. People take me more seriously by being here. I’m where music is, and with so many tech resources. I either need to take better advantage of it, or I need to do something else with my life. Someplace where bed bugs aren’t likely to follow.”