sex diaries

The Woman Who Meets a Potential New Boyfriend Her Very First Day in NYC

Photo-Illustration: James Gallagher

This week, a brand-new New York resident going on a Rockaways surf date with a potential new boyfriend: 25, single, Brooklyn.


8:30 a.m. Today’s the day! I packed all my belongings in a U-Haul last night and am ready to get on the road. After living in D.C. for two years, 15 minutes from my childhood home and surrounded by lifelong friends, I’m moving to Bed-Stuy. Never thought I’d be the one to move to New York, but here we are, barreling up 95 with everything I own clanking around in the back of an 11-foot truck.

4 p.m. Finally unpacked all my stuff with the help of my new roommate — a guy I went to college with — and one of my closest friends from college, who happens to live five blocks from my new place. I couldn’t help but wish I had a boyfriend to help me do this, as silly as that is. I’m a few months out of a complicated relationship with a guy who unceremoniously moved to L.A. to find himself. He doesn’t even know I’ve moved to New York. I sit on the floor of my unkempt new room and resist the urge to tell him.

8 p.m. I take the train to Manhattan to meet up with my cousin. He’s 29 and has lived in the city for almost five years now. We’re very close, and I love that he is so excited to have me here — it reminds me that I, too, am excited. We have oysters and many bottles of natural wine at a swanky Tribeca restaurant where he used to wait tables, so it’s mostly comped. We even sit next to a celebrity whose name I can’t remember. It all feels very New York.

11 p.m. We stumble to a bar close by where a friend of ours and a group of his friends are out. This is the first night the bar is properly back open since the pandemic started; everyone is beautiful and on their wildest behavior. I feel underdressed until a guy approaches me at the bar to tell me how great I look.

12:30 a.m. After a few espresso martinis, a friend of my cousin’s leans in and asks if I want to come with her to the bathroom. I nod yes, and she grabs my hand and leads me in, where she cuts us a few lines of ketamine. I do a line and she leans in close to tell me that she’d like to kiss me to make her girlfriend mad. I’m too drunk to make a smart remark, so I tilt my head back laughing and tell her that I’m flattered.

3 a.m. I’m on the verge of seeing double when a cute guy with bleached, spiked hair and nice eyebrows comes up to me and tells me he’s been watching me all night. I take his hand and we dance a bit. It feels good to feel wanted — I’m realizing that living in D.C. post-breakup, mid-pandemic made me feel like an old spinster. We drunkenly exchange numbers before my cousin gets me a cab back to Bed-Stuy.


10 a.m. First day waking up in my new apartment and I am so hung-over. I take some Advil and go on a run, despite the nausea. I return home to a text from A, the guy from last night, saying it was nice meeting me. I chuckle; I didn’t think he would even remember me, we were so drunk. I can barely remember what he looks like, but I’m intrigued.

12 p.m. My roommate and I careen the U-Haul south to the Red Hook Ikea to get some furniture before I have to return the truck. On our way, we see a bunch of Brooklyn-based comedians on a street corner being filmed doing some bit. My roommate can’t stop laughing — he also just moved here (although from L.A.), so living in New York feels novel to us both.

4 p.m. A and I exchange a few funny, banter-y texts about our day. Turns out we were at Target just a few minutes after the other. He makes a joke about not remembering much about me except how good he felt talking to me. It’s exactly how I feel, I tell him. We decide to meet up later this week. The excitement gives me the energy to go out again tonight.

8 p.m. Dinner at a sushi spot on the Lower East Side with two of my closest friends from college. I just left a demanding job at a public-interest law firm after realizing that lawyering is not for me, as meaningful as the work is. Now I’m on the hunt for a new job, though I don’t know what I’m looking for. Hello, quarter-life crisis, my new friend. I’m so glad to have these two to remind me that I have a lot going for me. We drink cold sake and laugh a lot and I tell them I already have a date lined up, which they are not at all surprised by.


1 p.m. I bike over to a friend’s new apartment in Fort Greene. It feels so good to be surrounded by friends and acquaintances after having a small, albeit tight-knit, circle in D.C. My friend makes us chicken tori katsu sandwiches and we eat them outside before walking around the neighborhood.

5:30 p.m. Rushing back to Bed-Stuy before heading into Manhattan for the night. I’m so not used to it taking a minimum of 45 minutes to get anywhere in this city. I bring a glass of orange wine — the only thing in my fridge — into the shower and try masturbating but can’t climax. Too much stress and adrenaline and not enough sleep, I tell myself.

7:30 p.m. At a friend’s birthday party on her rooftop back on the LES. I spend most of the night talking to an old Italian couple who own a restaurant my friend frequents. I can’t help but feel insecure having to explain over and over that I have no idea what I want to do with my life.

10 p.m. A group of us leave the party in search of some dinner. We end up at a trendy Greek spot before going for a nightcap at a scene-y Chinatown restaurant where another friend works. I end up getting drunk off Negronis and one by one my friends leave until it’s just me, my friend who works there, and some of the bartenders. We close out the place and head over to a nearby karaoke bar to continue drinking.

4 a.m. The partying continues in some guy’s shoebox Nolita apartment. We’re drinking and dancing and there are a lot of drugs and people who work in fashion. One of the guys is flirting with me, but my mind drifts back to A. I drunk-text that I’m excited to see him tomorrow.

8 a.m. Just now going to bed.


1 p.m. Late breakfast with a college friend who lives a few blocks away. As I’m leaving, I turn the corner and physically run into an old college hookup and his fiancée — he cheated on her with me when their relationship was just starting. This neighborhood is starting to feel like campus.

5:30 p.m. After a few hours on a LinkedIn deep dive looking for job openings, I shower, put on a bit of makeup, and throw on a pair of funky pants and a low-cut top. A and I plan to meet up at his place. It strikes me that I don’t even know his last name.

7:30 p.m. We meet up and I’m thrilled — my drunken haze was right, he’s so cute! We sit in the park across the street from his East Williamsburg apartment and talk about everything over a bottle of red wine: our families, living in the city, what we like to do. He’s a surfer and a musician with a fancy day job. Such a hot combo.

9 p.m. We walk to dinner around the corner and he holds! my hand! on the way there! I’m so giddy, even if a bit thrown off by how forward he is. We eat tacos and drink margaritas before heading to a bar closer to his place for a nightcap. He asks me questions about myself and actually listens.

11:30 p.m. I walk back to his apartment and, although I went into the night not planning on staying over, I’m really enjoying our energy. Back in his room, he plays me one of his songs on the guitar and I swoon. We start making out and he fingers me as we walk over to his bed. We have sex until we both come.


10 a.m. A wakes me up with a kiss, still naked and spooning me. I turn to him and we make out for a few minutes before having sex again. I kiss him good-bye and we make plans to hang out in the Rockaways in a few days.

12 p.m. I take the L to the G and smile the entire way. I decide last-minute to take the train to Greenpoint. I sit by the water and call my sister. She’s two years younger but so much less chaotic than I am.

7 p.m. I meet up with a childhood friend at a restaurant in Bed-Stuy for dinner. I see three (!) different people I went to college with walking down the street and am reminded that I ought to figure out my life pretty soon so that I can limit the number of acquaintances I have to tell about my jobless situation.

10 p.m. A texts me to tell me he can’t stop thinking about me. I tell him I can’t wait for us to surf together. I masturbate to the memory of us fucking before going to sleep.


11 a.m. Six days into living in the city, I finally resolve to unpack some boxes. Instead I go around the corner to buy a few plants. I arrange them in different corners of the room and tell myself I’ll do the rest later.

1 p.m. I walk to a close friend’s place who lives nearby and we Uber to a barbecue in Williamsburg. We have mimosas and hot dogs and I meet so many new people.

9:30 p.m. I bring my childhood friend with me to a college friend’s birthday party in Fort Greene. A is texting me saying he really wants to see me, and as the party is picking up I send him the address. He Ubers immediately, and I introduce him to everyone as if we’ve been together forever. We hold hands and act like it. It feels like a hot secret that we just met.

11:30 p.m. A, my childhood friend, and I get a car to a bar he likes back in Williamsburg. We immediately all take shots together before A and I slide into a booth and talk about how much we like being around each other. We walk back to his apartment and have sex on his couch, while he pulls on my hair from behind.


11 a.m. A and I wake up still embracing again. I love waking up next to him.

12:30 p.m. I get us an Uber back to my place and I change into a bikini top, bike shorts, and a white frock while he sits in my backyard. It’s our Rockaways surf day! We walk holding hands, as if we’ve known each other forever, to the nearby café for espresso shots and pressed paninis. We eat them on the train to Rockaway and talk about music the entire way.

2 p.m. I lie on the blanket and watch him surf before following him into the water. I’ve only surfed a few times before and by no means possess any skill, but he makes me feel comfortable. We share his board and he coaches me through the process: lie down, feel the wave, paddle hard, bounce up, stay up. I’m so turned on by him.

3:30 p.m. I catch a wave! Before diving back into the water I turn back to A, who pumps his fist in the air and smiles at me. I paddle back to him and we make out, bobbing in and out of the surf. I feel his dick hard through his suit and wrap my arms around his neck.

6:30 p.m. We make it to the ferry just in time for a perfect sunset ride back to the city. We stand on the top deck with his arms wrapped around me from behind, sharing warm Narragansetts and laughing about the drunk passengers around us. The sun sets orange on the skyline. I have a warm feeling I’ll know him for a long time.

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The Woman Who Meets a New Guy Her Very First Day in NYC