About a million years ago, I obsessed over dated this guy who, if emojis had existed then, I would have absolutely texted about exclusively in terms of the smiley face with hearts for eyes. He had Bad Fucking Idea tattooed in neon on his forehead. E.g.: When we first met, the person whom he exclusively referred to as his “roommate” was in fact his LIVE-IN GIRLFRIEND OF 3 YEARS. It’s possible we started hooking up dating about 30 seconds after they called it quits, and maybe she was possibly still moving her stuff out. Solid start to a relationship, real solid. Naturally, I elected to ignore the gigantic red flags and promptly fall in love.
I was 22, invincible, totally blindingly gaga, and, just absolutely possibly, a little stupid.
Anyway, we dated, we broke up, we dated, we broke up, and then proceeded to torture each other for years afterward by “being friends.” Both fancying ourselves writers we stayed friends under the guise of creative support and being, like, evolved humans, or whatever. In reality, I was still madly in love with him and desperately hoping that over Jack Daniels, our experimental short stories, and literary criticism, our romantic comeback would be staged. He would be in awe at what a devastatingly brilliant writer I was, remember how much he missed throwing me into bed, kissing me all over and falling asleep next to me — realize, in short, how much he just absolutely could not live without me.
So, when he started sharing details (that definitely didn’t make me nauseous or anything) of the epic confessional memoir he was writing that recounted of all the great romances of his 27-year old life, I was like totally cool with that because, like, we were totally just friends, and I was like, definitely dating other people and definitely not waiting for him to realize I was the love of his life. Ugh. Anyway. The idea was to use the women he had dated as the organizing structure of the novel. Each woman would be a different chapter, and using this framework, he’d tell all his stories of grand gestures and bellowing Bukowski from the tops of bars and doing blow off of a canvas in Chuck Close’s studio and whatever the fuck hipster bullshit he was always getting after. (Ok, ok, we had fun with a capital F, let’s be honest.)
I tortured myself listening to all this because I loved him so very much, but there was part of me, as a writer and New Yorker that actually did think it could have been something worth reading. We did, after all, raise hell in New York City. We had, after all, toasted with Johnny Rotten at the Hotel Chelsea and played pool with Little Steven at Ace Bar. It was the era of Pianos and The Strokes and smoking in basement bars like Lit. We were in constant pursuit of Cool. This was our very own, bourbon-fueled, converse-wearing, sucking the marrow out of life Hungover Poet’s Society. Heartbreak and destruction were but a natural byproduct of Life, of Experience, of our 20s. And if anyone had the lying embellishment skills to tell a good story, and pull off a novel like that, well, he really did.
Perhaps picking up on the fact that I wanted to vom each time he brought the book up, he was quick to let me know that of course, of course, I was in the book. (WAIT, so, you’re saying there’s a chance?) First I was Chapter 5, then I was Chapter 3. After some shifting around I was reassigned to Chapter 6 and then, finally, I was Chapter I-Didn’t-Give-A-Fuck. After waayyy too many years of Heart-Torture and late-night Heywhatareyouupto’s, I got waayyy too burnt out on his whole Deal. It always stayed civil, but finally (FINALLY) I was Just Over It. Plus he got married, but, whatever.
If we were to use his organizing structure — and we are, thanks, appreciate it, you owe me one anyway Fuckface — then he would be my Chapter 1. Our whirlwind, drunken, roller-derby of a love-affair kicked off my dating life in New York City — that still isn’t fucking OVER. God kill me. — and what ensued in the following years, I think was always a little bit informed by him. I want, stability, sure, but I want Magic and bravery and rock and roll and someone who will jump with me. When I was 33 I met the man that I was sure was my Last Chapter. We had really and truly started to dig in and build a life together, and, then, one day, it was inexplicably Over. So, I am 37 years old, rapidly careening towards Totally Over It years old, and find myself, once again, single.
I have been dating in this city for the past eighty-five 16 years, and, I am firmly convinced that when Dante Alighieri, the lauded Italian poet of the Middle Ages, wrote his Inferno, describing in horrifying detail each of the nine circles of Hell and the assortment villains, reprobates and ne’er-do-wells being tortured for eternity, he was writing about not the mythical underworld of Tartarus, but rather of dating in New York City as a 30-something. I’ve met men in bars. I’ve met men at work. Most of men the men I’ve been romantically involved with, however, I’ve met through the fuckery known as online “dating”. I find myself somewhere I didn’t think I’d ever be in my mid-30s — Omg, wait, is 37 LATE 30s? Ugh. Anyway. I find myself somewhere I didn’t think I’d ever be: crafting witty (wittyish?) opening lines and awkwardly shotgunning drinking a glass of Sav Blanc whilst trying to determine if the Cylon man sitting across from me is even tolerable let alone desirable.
I have no answers, but I do have some stories. Some are good stories, some are bad stories. I am not bitter (fucking miraculously), but I am, obvs, SALTY AF. What follows is a ridiculous deep dive into my dating past. I can promise honesty, compassion where it is warranted, but to all the men I’ve dated: you have been weighed, you have been measured, and you have been found wanting.
Let’s do this. Up first: The Hipster
Ugh. Anyway. 