October 2015
On our first date, late in the night at a cocktail bar in East Village, he kisses me so suddenly after hours of conversation that I can’t breathe. In the moment, I am certain I have met the person I am going to marry. I let the singular feeling of that first kiss — the kiss that spun my head out of control, the kiss that made me instantly want to give up everything I had ever had for him — carry me through eight more months, three of which are pure elation, the following five that almost kill me.
Four years later, we run into each other at an interpretive dance class in Brooklyn. We do not speak.
OCTOBER 2019
I want someone who belongs to someone else, and to make up for that, I say yes to a date with a man who, I think, could possibly be the nicest man I have ever gone out with in my tiny, little life.
On our date, he keeps going to the bathroom and, on the fourth time, he turns to me to say, “Just so you know, I’m not doing drugs in there.”
This leads me to believe he is, in fact, doing drugs in there.
February 2019
It is a Sunday and I am not doing drugs in the bathroom, but I think, maybe, the bartender is. It’s the afternoon and I’ve never been here before, but I sit by the windows, alone and writing. I don’t mean to befriend the bartender (I never do), but somehow, now, it’s midnight and I am helping him close the bar and then, here I am, having a conversation at a new place down the street, tucked in a booth with a beer and the bartender and a man from Italy who speaks exactly no English.
I do not know if this counts as a date. I do know that I love the feeling of instability in a Sunday night, sitting at a bar with the stranger I met just a few hours before, his hand intertwined with mine. I love the feeling of making a connection, no matter how quick, with someone who’d never be suitable in my daylight life.
As we’re in the booth, I am struck by the feeling that I love living in New York because of situations like this. The city hands me choices and I can be aware that I am taking the wrong ones, but I know they are mine to make.
March 2019
I have, once again, broken up with the man I refer to as my boyfriend. (He is not). “It’s really over this time,” I tell all my friends. (It is not).
I go see a band with my friends on the LES and proceed to get wildly drunk off IPA’s. I am Fun. I am the Cool Girl. I am Not Thinking About My Ex. We go to another venue with the band and I compliment one of the members shirts — it says “Michigan Dad” — and he, in return, compliments mine — it is a crop top, filled with polka-dots. In the middle of the bar, sealing my place as Fun and Cool and Laid-Back and Wild, I take off my shirt and make him switch with me. We wear each other’s outfits for the rest of the evening and return them a week later on our second date.
I break up with him over text message two months later, partly because I am no longer that into it, mostly because I don’t have the energy to keep being the Cool Girl.
August 2019
I meet a comedian, not my first one, at one of my roommate’s comedy shows. We go out on a date the following Sunday night and he pays for appetizers and drinks at a cute bar in Nolita. I tell him I’m impressed; he tells me my bar is low.
The last comedian I’d met at one of my roommate’s comedy shows waited until after he’d kissed me to tell me he had a live-in girlfriend. This man has no idea how low the bar is.
July 2018
In May of that year, we visit DC and meet a bartender who says he will come visit us. We don’t believe he will.
He does.
I don’t realize we are going on a date, so I invite my coworker and brother to get drinks with us. We all meet at a fancy speakeasy and it becomes abundantly clear we are on a date to everyone but me.
In the course of a weekend, we essentially go through all the stages of a full relationship — I meet his friends, we go to brunch, he gets a thigh tattoo to commemorate the visit. As I walk him to the train station as he is leaving, I wonder if anyone will ever like me this much again.
May 2019
I liked someone that much, once. It was in 2016 and I fully believed I was in love with the bartender at our local bar. (I was not). We went on a singular date, he told me we couldn’t be together and, for the next eight months, I tried to convince him otherwise. The entire situation culminated in a terrible evening which ended with me refusing to leave his bar until 5 am and us not speaking for almost three years.
In 2019, in May, we start talking again. He is nice and great and funny and I like him so much, but not as much as I did in 2016 and I can’t figure out why. We go to a concert in Brooklyn and, when it’s over, he buys me pizza. Sitting across from me, he says he can tell I am still in love with my ex. I do not correct him because he is not wrong.
We do not see each other again.
July 2019
And, he was right! — I am (still) in love with the man I (still) refer to as my boyfriend (he, still, is not) and have a full on breakdown when we decide to end it for what we both agree will be the last time. (It is not).
I have to go home, all the way home, real home, back to Massachusetts to deal with my feelings after I’d spent an entire week crying at my desk, making me realize that this was the worst I’d ever taken any of our break-ups.
And, after I come back to the city, I dream about him every night for a month, waking up in cold sweats despite the summer heat pounding its way through the crack in my window, the crack that never would have been opened had he been sleeping with me because, while I prefer it naturally hot, he prefers to sleep in the artificial cold of the AC and I realize then I’d give up all my preferences for him, I’d give up anything I wanted for his comfort and that’s why we can’t be together. It’s not just that he doesn’t love me as much as I love him.
It’s that I make myself disappear around him.
March 2016
I do not want to go on this date, but after weeks of him asking, I finally give in and say yes. He has to finish his pool tournament, so we don’t leave for the date until after midnight. I am exhausted. We walk to the date location and it becomes clear to me that he has planned to take me to the TGI Fridays in Union Square. I am incredulous.
Because it is after midnight on a Sunday, it is closed.
My date turns to me outside the closed chain and asks if I like margaritas because he knows “a great little place for them.” I say, “Yes,” because I love both margaritas and little places. We get in a cab and I assume we are heading to a hip place downtown, a hole in the wall, some place I have never heard of.
He takes me to the Dallas BBQ in Times Square.
June 2018
The Times Square Date holds up as my worst first date for awhile — until I meet the boy I refer to in stories as Fist Fight Guy.
This is because he gets in a fist fight with the bouncer on our first date.
Against all odds, we keep seeing each other and it somehow turns into a very lovely platonic friendship where we hang out almost every Thursday night.
The day after we decide to be just friends, we spend 14 full hours together, starting with us eating lunch on my roof and ending with us traveling to Queens to see my favorite band. I cry and he buys me a grilled cheese. Months later, we go see his favorite band. We both cry and I buy us tequila shots.
No one understands our friendship. Neither do we.
February 2020
I spend the day in the hospital; I am the emergency contact while my friend gets surgery. I am there for 12 hours. In that time, I finish my work, my book, my snacks — I get bored and download a dating app, the first I’ve had in almost three years.
Immediately, I am shocked (and flattered) at how many messages I get, though I do realize this is probably because my photo is me wearing a bathing suit, drinking champagne in a kiddie pool on my roof. Overwhelmed and excited, I schedule a date for every night of the following week.
Later, I cancel all but three. One is good, one is great, one is with a male model-slash-songwriter who tells me he is fasting for fashion week and makes me watch his self-described “Switchfoot-esque” music video at the bar after showing me his cat’s Instagram feed. He tells me the worst first date he ever had was when a girl ate a pizza in front of him.
I don’t know how to tell him this is my worst first date, so instead, I go home and eat a pint of ice cream. When he texts me the next day to say he had a great time meeting me, I say, “Thanks.”
September 2015
I lie about my worst first date story. The real worst first date I’ve ever had was when I didn’t want to sleep with the guy, but he wouldn’t take no for an answer and followed me home. I had to run into oncoming traffic to get away from him.
I do not tell this story because it is not funny.
August 2019
A boy passes me a note in the middle of a show. The note says that he thinks I’m cute, that I have a great smile, that we should go on a date. We pass the note back and forth and, through it, make plans to leave together. We do, in the middle of a set.
We have not yet spoken.
It starts raining as we leave — pouring, really — and we go back to his place, changing out of our wet clothes into his warm sweat pants, eating bagels, watching TV. I fall asleep forgetting that this is a stranger, that no one knows where I am.
I wake up in the morning fine, full and comfortable.
August 2018
I don’t call what we do dating because we are friends. I tell my roommate that I like how there is no pressure because we are just buds who go get beers in Brooklyn and then fall asleep listening to music in his bed.
She tells me I should work in PR because that’s just another way of spinning dating.
October 2019
It’s been almost two years — we’ve broken up and gotten back together multiple times, but never with the title of exclusivity. We’ve never gone more than three months apart and, whenever we start another new era of us, we begin with another First Date.
This has happened so many times that I can no longer count or care.
No one knows. I lie to my friends, constantly, about who I am with... it’s easier than listening to them repeat, justifiably so, that he’s just going to break my heart again.
In mid-October, we get beers after work and he asks me to be his girlfriend, for real this time. He wants to do it, tell everyone, be together, live the kind of life we’ve been piecing together, pretending to have, since 2017.
I want to feel happy — this is what I have always wanted! this is what I have been waiting for! — but, instead, I just feel tired.
We break up, for the last time.
(It is).