8 True Stories Of One-Night Stands

Photo by Natalia Mantini
Sex. Strangers. Intimacy. Awkwardness. Ecstasy. These are just a few of the sometimes-disparate ideas that come into play when we talk about one-night stands. Because the truth is, this is an experience that a lot of women share, but experience entirely differently. It's personal. Even when it's not.
Some women swear it's the purest type of sexual encounter (most famously, Erica Jong). Others find themselves feeling deflated afterward, whether or not they had level-set expectations beforehand. And others still see it as just one half of the coin of sexual experience — where physical, carnal pleasure and emotional intimacy can't co-exist.
And, while we all share the sexy, thrilling parts of these stories with our friends, we so rarely talk about the emotional ramifications (both good and bad) and the less entertaining details that add up to reality. All of which is completely worth discussing. So, we sat down with eight different women to get just that. Ahead, their takes on eight very different experiences — orgasms, disappointments, and all.

(*Some names changed at the request of the women interviewed.)
1 of 8
Illustrated by: Abbie Winters
Tracy Bloom, author of No-One Ever Has Sex On A Tuesday

"Our eyes met across a dusty dance floor. I'd last seen him over 15 years ago. He had been my first love and our relationship consisted mainly of awkward teenage fumblings in awkward locations. We skirted each other like matador and bull until alcohol and slow music led us to stumble against each other in a clumsy reunion.

"So, we went back to his place — where I discovered he'd grown into a rebel rejecting a conventional bed for a sleeping bag on nylon carpet. We lay there and reminisced about those awkward teenage fumblings until we partook of some very awkward 30-something fumblings.

"He said he'd phone. I knew he never would. Nights spent stalking the phone as a 15-year-old had at least taught me he wasn't the type to phone. But, it didn't matter. I didn't care. This one-night stand had given me closure. My first love was no longer the boy who made my heart race like no other man had, ever since. He was just a man who slept way too close to the floor, surrounded by nylon. Heart vacated, it was now available for new occupier."
2 of 8
Illustrated by: Abbie Winters

"I met a guy on OkCupid. We went on one date, didn't have sex, but continued to text when we were both drunk.

"One night, I was especially wasted and right around the corner from his apartment in Brooklyn. So, obviously, I gave him a call, and he told me to meet him at a bar nearby. We had a few drinks, and then decided to go back to his apartment to smoke a joint on his roof.

"So there we are at 2 a.m. on the roof of this HUGE loft-style apartment building in Brooklyn, totally stoned, and he goes in for the kiss. Things progressed pretty rapidly from there, and before I knew it, we were both naked from the waist down, and he was pulling a condom out of his pants. We had sex in the middle of the roof, in the middle of the night, in clear view of anyone and everyone who was in the apartment buildings around us.

"I spent the night (in his bed — not on the roof), and in the morning we split a huge stack of pancakes. I haven't seen him again. Not coincidentally, I also haven't fucked on a roof since."
3 of 8
Illustrated by: Abbie Winters

"I put an ad on Craigslist Missed Connections for a girl I met for one second at a riot grrrl show in someone's loft. We'd been looking at each other all night and then she introduced herself to me before getting swept up by a crowd of moshing people who smelled like they didn't believe in deodorant. I thought it was really cool that she didn't mind being tossed around like that. She was wearing a red bandana low on her forehead and lots of black eyeliner. She looked like an andro Natalie Portman and she'd been staring at me as though she already knew we were going to sleep together. But, she left without saying anything more and so I found myself posting about it on CL the next morning. Not because of any sort of Cinderella fantasy; I thought she was hot and seemed really cool — way cooler than me, at least, which is always appealing. I figured she was the kind of girl who had been dating girls since she was 12, who would be assertive in her interest, who could read a map, and who could maybe fix my sink.

"She answered the ad about an hour after I posted it. She said she thought it was romantic. We were both under 21, so we met at a cafe and had tea. She talked the whole time, which was fine because I was too nervous, and then she followed me back to my apartment. When she saw the explosion of beauty products strewn across my dresser, she exclaimed, "You're such a girl!" She sounded disappointed. To be fair, at the time, I had a nearly-shaved head and mainly wore ripped jeans and tank tops. I was still my fairy-princess femme self on the inside, but was enjoying the experience of being visible to other queer women, through pretty standard visual signifiers. So, the fact that she didn't realise I would turn out to be 'such a girl' wasn't exactly her fault. Plus, I had said so little during our date — while I knew the basic outline of her life story, all she knew was that I was a good listener.

"We then proceeded to have what turned out to be super-awkward sex. It seemed that we each expected the other person to take charge. It also came to light that, despite her initial swagger, this was actually her first time. I found this to be extremely disappointing — but also feeling guilty about it. But it felt too late to turn back. When I woke up alone the next morning, she had left a note in careful script on a crumpled receipt that read, 'It was beautiful. You are beautiful.

'"I felt very confused. What had been beautiful about our anxious fumbling? If anything, it seemed to me that maybe she had gone into it expecting to have a beautiful experience from the moment she declared my CL ad romantic, and was determined to name it that regardless of what happened. We had both projected different things onto each other, and somehow our night together hadn't ruined her vision of me. I guess she was more committed to the fantasy of me than I was to the fantasy of her. She called me a few times and I didn't pick up, because I was young and didn't know how to politely turn someone down. It's been over five years, but I still see her every now and then at queer parties. We usually nod at each other, but that's it. We've both grown our hair out and are dating butches."
4 of 8
Illustrated by: Abbie Winters

"I was moving out of New York in a week. I had never had a one-night stand. I was out with a few guy friends that I barely knew. The club was full of overeager young financial types, but I was lucky to be around a few 'nice' guys. My friend introduced me to a colleague of his. Apparently, we knew some of the same people from back home. Having mutual friends made us way too comfortable... we took way too many shots and danced way too close in public.

"I decided that this was my chance, that I could have that one-night stand with a nice guy, so I asked him if he lived alone and if he wanted to go to his place. His eyes opened wide. He grabbed my hands and we were in a cab in what felt like 30 seconds. He lived in a barely furnished apartment on the UES. We started fooling around and it was okay, but a little bit awkward. Something felt off that I couldn't quite pinpoint.

"And then, he asked me, 'Want to do it against the wall?!' I looked at him in disbelief. In a wave of panic, I realised that I was probably his first one-night stand as well, and that he probably had pretty limited sexual experience. When I wasn't going down on him before sex, he was genuinely surprised and said, 'You're not going to go down on me?!' That threw me off. I really couldn't see how anyone could just expect another person to give them head. He wanted to try all these things he'd heard about somewhere.... He spit out different poses and tried to position my legs all crazy. And, I remember thinking that if I was actually in a relationship with this guy, it would have been okay for him to ask me to try new things with him. But, I didn't trust him and I felt like his weird science experiment, which is what turned me off. Looking back, he was kind of my own experiment as well, so maybe we're even?

"Going in, I didn't think much about it. It was just something I wanted to experience, and I knew NYC was the place where it needed to happen. Afterward, I felt pretty stupid. I literally told people this was the stupidest thing I had ever done. Plus, having sex with someone I didn't actually like was boring. I haven't had a one-stand stand since."
5 of 8
Illustrated by: Abbie Winters

"I lost my virginity at a young age to the older boy across the street in the back seat of a car. It was in the park, in the middle of the day, in a planned meet-up during a run. He wanted it. I had a crush. And so I gave it to him. And it never happened again.

"The experience somewhat cheapened sex, which felt nonchalant to me after that. In some ways, that day set the precedent for my many sexual flings that have since ensued.

"The moment I go home with someone, I judge whether or not I truly think I can see something further developing with them. Do I really like this guy? Can I see myself telling him my deepest secrets? Putting my heart, body, mind, and soul in their hands? I genuinely believe that after a good first date or night out with someone, I know what my intention is for them.

"If my body wants it, but my heart and head say otherwise, then I know...I'm in for a one night stand. I manage my expectations for that person on the spot. It's okay if I never see him again, or if he doesn't call. I only sleep with someone on the first night if I don't particularly care whether or not I see them again. I know he won't be my forever prince, and therefore, will make him my knight for a night.

"Like last month, when an adorable guy showed me an apartment. We spoke for 30 minutes after the showing — it was flirty, fun. We met a week later for drinks in a charming, dimly lit corner bar. We talked about life, our families, and aspirations. There was a strong commonality and connection. We went back to his place. In the moment that we were moving from the couch to the bed, I judged the situation —whether or not I would go all the way with him. As charming as he was, my gut told me: He is not the one. And not because there was anything wrong with him. He was just missing something intangible that would reserve a place for him in my future. So, we had a one-night stand. The weirdest thing about it, though, was that throughout the entire sexual experience, his face kept changing. Every time I looked at him, he looked like someone different. Like he was wearing a camouflage image-changing suit, to hide his true identity. It was trippy and distracting. I figure it's because I didn't really know him. I wasn't used to his face. And movement.

"Since then, I've decided one nights stand are an impersonal affair encased in an intimate moment. They are an easy way to satisfy my desire for interpersonal connection. A way to protect myself from being vulnerable and susceptible to someone else's influence and power. A way to keep my emotions separate from my experience.

"I'm in my mid 20s with 50-plus sexual partners — from one night stands to long term relationships to week-long whirlwind flings. I've taken v-cards and stolen hearts. Mine has only been broken once. And since then, I see that how you give yourself to someone is just as important as who you give it to. Sex has two different roles — hedonist pleasure or intimate love. Don't expect longterm intimate love from a one-night stand if you want to avoid disappointment. And hold back if you want to hold on."
6 of 8
Illustrated by: Abbie Winters

"I was apprehensive about sex as a teenager. I didn't feel ready, and I definitely harboured fairy-tale fantasies about my first time being with someone who felt like a soul mate. In college, I carried that with me, so I hooked up and went almost all the way, but never quite there. And by my early 20s, the weight of my inexperience held me back in relationships — out of fear of being discovered for this thing I was missing, this knowledge that I didn't have.

"Eventually, I slept with a guy about five dates in, and stopped seeing him a few dates after that. So, when I started seeing my next boyfriend, my experience was pretty limited. When that relationship, which had consisted of a lot of missionary sex and limited orgasms, ended six months later, I still didn't feel like I was where I was supposed to be, as an adult in charge of her own sexuality. I didn't really know how to ask for what I wanted, or really, how to figure out what I wanted, when I wasn't on my own.

"Essentially, I had lost my virginity at 26, so this moment of singledom felt like my opportunity to do something a little reckless. I joined OkCupid. I laid low for a while, emailing guys and going on some dates, but never feeling comfortable enough to go home with any of those men. And then I heard from a professor who was a few years older than me, and emailed him back just once before asking if he wanted to meet for a drink. He did. We went out on a Sunday night and hit it off. I didn't feel a real connection — or in all honesty, real chemistry — but I did feel pretty comfortable with him, having easy conversation and laughing a lot. Three drinks later, we left, made out in the street, and headed in the general direction of both our (conveniently neighbouring) places. When he offhandedly was like, 'I don't supposed you want to come up, just for a drink,' I surprised him with a yes. We went up to his place, started making out, and things easily escalated. And for the first time, maybe because I didn't feel any real pressure or expectations, I was able to be more vocal about what I did and didn't like. I put his hands where I wanted them. I stopped worrying about whether the jiggle around my middle was going to be unattractive if I got on top. And ultimately, I still didn't orgasm that night, but I did change some of my own ideas and inhibitions around sex and intimacy.

"But still, the next morning, I woke up before 6 a.m. and felt really uncomfortable. I didn't want to be there. So, I lied about an early meeting, left, and never called him again. And he didn't call me, either. The only problem: Despite the fact that I didn't want to see this guy again, the fact that he clearly felt the same, and was on the same page as me, felt like tacit rejection. Which was hard. That's why I never did it again, but in a weird way, it's one of the most important things I've ever done for myself."
7 of 8
Illustrated by: Abbie Winters

"It was her first time. As in body shakes, hesitant hands, and overall timidity. But, let me back up and give a little back story.

"Rebecca and I were set up by mutual friends and we decided to meet up at old town bar on 18th street. I've found with lesbians (at least the ones I hang around) that the 'typical' one-night stand where two drunk strangers meet at a bar and go home together at 3 a.m. rarely happens. I guess reasonably sober conversation is needed first? I knew right off the bat that we had a connection. We had many mutual interests — art history, weird families, and a distrust of social norms, to start. So, I decided to do what a recently single girl does after three Heinekens — invite her back to my place. She rode on the back of my bike and we made it to my apartment around 2:30 a.m. I knew she was inexperienced, so I opted to take things slow. Instead of ripping off her clothes the moment we got in the door, I made her a drink and showed her around the apartment until we got to the bedroom. After some light making out, I noticed she was shaking and a bit unsure with her hands. I said to her, 'I don't want to pressure you, we can absolutely just go to bed if you want.' Her response was a simple 'No, I want to.' So, I kept going. It. Was. Terrible.

"The strange thing, though, was that I liked this girl. She was funny, intelligent, attractive, reasonably sane. All the things I'm usually a sucker for. But, from the very moment she reached to undo my bra, I knew it was doomed to fail."The next day, she texted me and said 'Last night was wonderful. We should hang out some time this week.' I never texted her back. I know what you're thinking; I am a complete douche. And no, it was not one of my finer moments but I have also never been good with disappointment. I just had no idea how to tell her that we were not ever going to see each other again because she was horrible in bed. My friends all said, 'But you could teach her right?' Let me tell you: Ain't nobody got time for that.

"We were all virgins at one point (I was significantly younger than 24, but still) and I think we all remember what those first touches felt like. But what happens when something you think is a one night stand, is someone else losing their v-card? (To clarify, I only found out much after the fact that she was in fact a virgin.) Is it your responsibility to let them down gently? Because chances are they are not going to be orgasm-inducing in bed. But then again, isn't that counter to the purpose of one-night stands? I have never had an orgasm from a one-night stand, yet I still continually have them. Why? I'd like to think its because I can. I'm young, single, reasonably attractive, and live in NYC, which means I could essentially have someone new every night of the week if I wanted to. Why would I? It's exciting. It's distracting. It is a good story to tell over brunch. Do they ever amount to much? In my experience, no. But do I regret any of them? Absolutely not. Not even with the virgin."
8 of 8
Illustrated by: Abbie Winters

"In my varied and rather random sexual history, I have had only one legitimate one-night stand. And, I’m pretty sure as far as those types of encounters go, I nailed it (pun intended). I met Jeremy* at a downtown bar I frequent on weekends when plans are lacking. This particular evening I was drinking with a friend and my sister, who were both visiting from out of town. We started talking to Jeremy and his friend about the basketball game and proceeded to verbally spar for the remainder of the evening. I wasn’t so much attracted to Jeremy physically — he was cute enough, but not really my type. He was about my height, which as shallow as it may seem, is usually a deal breaker.

"But, it was his personality that assured that my going home with him would be a good time, at the very least. I’m very cerebral and he had the ability to talk intelligently about an impressive range of topics. There was a certain ease to conversing with him. And, at around 1:30 a.m., he asked if I was going to go home with him (albeit, a little more crudely than that).

"This may have offended some girls, but I found his honesty and brazenness to be fun. There was no mistaking what this was and I was surprisingly more okay with that than I thought I would be. When we got back to his place, we shared a joint, which coupled with the amount of drinks we had had meant that I remember very little of the main event. Oops. But, when I woke in the morning, Jeremy was just as jovial as he had been the night before. We laid in bed for two hours and talked about our lives before I got dressed to leave. There was no exchange of numbers, although that wasn't the last time I saw him. We live in a small city and we have bumped into each other and sort of smiled but never spoken. And I am okay with that, too."

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