“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.