I don’t know why I write. I don’t know why I do anything, and it’s honestly one of my favorite things about myself. Other than my legs. And my necklace collection. And the pink wigs I put on my Sonos. Oh, and my ability to be single for 40 years and then get into my first long-term relationship with literally the man I was always supposed to be with. I’m a skeptic, but when I was 23, I asked a clairaudient named Patricia about this guy, Trey, I was infatuated with, who she told me was going to be a lawyer (spoiler alert: he is now a lawyer in Connecticut), and she told me not to “worry too much about dating now. You’ll find the person you’re looking for but not until later. You have more living to do first.” At the time, I was pissed and vowed to prove Patricia wrong, so I started a Tumblr (yes, it was the halcyon days of the early-2010s internet) where I was determined to document the 100 dates I would go on. My best friend, Lauren Wilkinson—yes, that Lauren Wilkinson, of American Spy fame (sidebar: Lauren was the person who told me about Patricia)—said at the time that dating was “a numbers game.” We decided to go on as many dates as possible, and the first person to go on 100 dates would win. I typoed “win” as “wine,” probably to remind you, dear reader, that as soon as I’m done writing this, I’m hightailing it to the gay sports bar to catch the rest of Game 3 of the Knicks vs. the Spurs, complete with bubbly rosé. Anyways! I’m not a competitive person—but I truly, madly, deeply had to beat Lauren at dates. I got on all the apps, all the sites, went to all the singles’ nights, meaning I went to gay bars alone (I know), and any time someone asked me out on a date, I had to say yes. No excuses, no restrictions. If they asked me out, we went out. Each guy had a corresponding entry on the 100 dates Tumblr, and each title was their moniker: “Phish-y Lawyer.” “Baby Baby Baby.” “Bar Farter.” And it was actually kind of…fun? Not the dating part—dating is fucking horrible. It was the writing. For the first time in my postcollegiate life, I had a sustained writing practice. Everything in the world—every thought, nuance, song, and boner—became fodder for it. It was an instinct I let myself trust. Unfortunately, I didn’t beat Lauren at the date game because the project had its intended effect: Around date 30 or so, I met someone whom I then went on another date with, and then another, and then it was just him. And, surprise, surprise, it turned out I wouldn’t have dated him if it weren’t for playing the numbers game. He was 23 to my 27, and as a rule I didn’t date younger guys (the last time I’d dated a 23-year-old, I was 18, but that’s a tale for a different essay I’m writing in my head called “Getting Fingered in the LGBTQ Center All-Gender Bathroom”). When he dumped me two months later, I was shattered. All that effort I’d put into dating, not just with the 100 dates thing… I saw how everything I did in my life was a prelude to men. And for what? So that I could sit in a waterfront park in Williamsburg crying over a guy while listening to Lana Del Rey like every other goddamned gay?! Whatever men offered, they weren’t going to give me myself. That’s my job. I looked into the water and promised to date writing the way I dated men. A year later, I started working on what I thought would become the world’s longest Tumblr post, called IRL, which eventually became my first book. And the rest, as they say, is the future. So why do I write? I really don’t know. I just kind of have faith that if I start somewhere, I’ll get to where I need to go.•
This article appears in Issue 37 of Alta Journal.
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