how to NOT have a one-night stand
i gave it the ol' college try
I was horny and over-monitored, thanks to recently moving back home with my parents in the suburbs after quitting my 9-5 magazine job. I was 31, and I wanted to get laid. I knew the easiest way to do this was to finally have a one-night stand—the infamous sexlore that had forever eluded me. From my understanding, a one-night stand was a no-strings-attached situation. Just sex. A transactional tryst. A satisfying if not literal “I’ll scratch your back if you scratch mine” situation.
I already knew the perfect candidate: Will, a friend for almost a decade from New York (this fact alone easily disqualifies him from being a true one-night stand but let’s stick a pin in that for now). It was supposed to be an easy plan; I could get off during a weekend trip I was taking to Manhattan to visit old haunts and friends, while also checking it off my “sex to-do list.”
I chose Will for a couple of reasons. Twelve years my senior, Will was the kind of guy who took more pride and effort to secure an apartment in a respectable co-op building than securing a respectable long-term relationship. So I figured he was an expert at the ol’ “don’t call me, I’ll call you” bit. He was also the friend who had always been there to help me out in a jam, like picking me up at the bus station when my ex deserted me or helping me move into my tiny dorm. He also once told me once he would “never let anything bad” happen to me, which I remember brought a warm and fuzzy feeling to my chest, so I figured he’d be more than willing to assist me once again in my time of need.
For my visit Will planned to take me to my first Knicks game, followed by dinner at a new hip Italian restaurant in the West Village. It was there when I thought I would lay it all out on the nicely set table, like proper grownups. Maybe throw in a punny reference to, “Voulez-vous coucher avec moi ce soir?” to lighten the mood. Instead, as I looked across the nicely set table at Will, I choked. Literally. Well, that’s probably an exaggeration, but I did swallow a fish bone. Which made me feel like choking because I was having a mini panic attack.
“I think I’m choking. I swallowed a fish bone.”
“You’re not choking.”
“How do you know?”
“Well, first of all, you’re talking to me about choking. You can’t talk and choke at the same time.”
“What if I die from swallowing a fish bone?”
“Brianne, you’re not going to die. At least not from your fish puttanesca.”
A few glasses of water later, and further reassurances from Will that the likelihood of dying from ingesting a small fish bone was slim enough for me to resist calling my parents as part of my last rites, I was able to refocus on the task at hand – getting laid. Will was paying for the check, so it was go time. Truthfully, I’d been thankful for the distraction of my nearly dying because suddenly my sexy plan didn’t feel so sexy anymore. The main offense being, did I really want to see Will naked?
Sure, there’d been some ample elbow and knee grazing at the Knicks game, which I sucked up like a pheromones-hungry bloodhound, desperate for a whiff of desire, but in our ten years of friendship, I’d never found him sexually attractive. Yes, he was good in a crisis (as was proven that night), but when it really came down to doing it for me, it wasn’t a matter of how many foul shots you could score, but more if I wanted to see you hit the showers. Was it worth throwing in the towel just to cross off a one-night stand from my “sex to do list”?
I decided it was not. So I hugged Will goodbye, and headed back to my hotel, alone.
Okay, I may have been a noob but I wasn’t a nun. After having dinner with my friend, Olga the following night, she convinced me I was being an idiot for not having gone through with it.
“What is wrong with you!” She said, practically spitting out her wine. “You’re single, he’s single. You want to have the sex. What’s the problem?”
Feeling a little pussy-pressured, I texted Will, asking him where he was. Funnily enough, he was at a dive bar in the East Village, just a few blocks away. “Go get some!” yelled Olga.
On my walk over I convinced myself sleeping with Will was a good idea. I was a 31-year-old woman. It was perfectly normal to want some good old fashioned dick. If I wanted to have casual sex with someone for one night, dear God, I owed it to myself to try to get it.
And as it turned out, it was pretty easy to be easy. All I had to do was show up. After meeting up with Will, and listening to him talk endlessly about his newly renovated apartment, I used his obsession with pocket doors as an excuse to, quite literally, invite myself into his bedroom.
“I hear pocket doors are really good for small spaces,” I said.
Suddenly I was Joan Collins.
I ended up sleeping over, but I woke up with a sex hangover. I regretted both the sleeping over part and the sleeping together part. Maybe it was because of the premeditation of the act or the high anticipation of it that left me with such mixed results. Whatever it was, “it” didn’t live up to my expectations, and I felt horrible about the whole thing. I was worried I had veered our friendship into a no safety zone, and thereby had, effectively, run it off the road. As much as I didn’t want to admit it, there was always something more between Will and I, including what I felt was an unspoken affection from his end. At the very least, we both respected and cared for each other, so I shouldn’t have been surprised that the guy who once left a date mid-makeout to rush to my side after I got into a taxi accident, suddenly wanted more than one night. Now he wanted to spend the entire day with me.
“I can’t,” I said. “I have lunch plans.”
“What about after?”
“I’m going to the Guggenheim.”
“What about dinner?”
This wasn’t supposed to happen. How did my “wham bam, thank you ma’am” turn into something as long and drawn out as the last season of Game of Thrones? How did I possibly mess up a one-night stand?
Oh, that’s right. We were friends. With a meaningful history. Rookie mistake.
So, of course I said yes to the dinner. And when Will asked me if I wanted to go on a vacation with him next month, I said yes to that too. And when he started calling me everyday during his lunch hour, and then after work, wherein he talked more about pocket doors before he moved onto barn doors, I not only picked up the phone, I started looking forward to his phone calls. And before I knew it, we somehow started dating each other. And then, months later, when it all blew up in my face, literally on FaceTime, when he called to break up with me, I was the one who cried and cried for weeks. And the only reason why I stopped crying was because of Geoff, the second guy who I “almost, not really” had a one-night stand with that summer.
Geoff and I had met a few years prior in a comedy writing class. We shared the occasional drink after class, discussing our writing goals and favorite funny movies, and would drop the occasional text, usually something along the lines of, “Hey, can you check out my latest script?” or “Hey, I heard you quit your job! Congrats!” About a month after my breakup from Will, I heard from Geoff for the first time in a while, and soon our occasional text message turned into a daily text message, and soon our daily texting turned into full-blown daily sexting.
“Your messages are like little Christmas presents,” I said to him.
“Your ex was an idiot for letting your sexy ass go,” he said.
Geoff was away in Europe until September, but upon his return to Toronto, we knew we were most definitely going to have sex. This was a surprise to me. Like Will, Geoff was a buddy and not someone who I’d been attracted to, but for all intents and purposes, Geoff was rebound sex, and I had never had one night of rebound sex before. Once again, I thought I owed it to myself to be the type of woman who, short of wearing a trench coat without anything underneath, dared herself to try it.
The night was almost like a déjà-do. Once we started getting into it, something was …off. I think with all the heavy petting descriptions and sexy pictures being exchanged weeks before, there was an incredible build-up to our evening together, and that was both to our detriment. I woke up the next morning with an even worse sex hangover than before, confusion and regret surged through me, which, sadly, not even a cup of Geoff’s Bulletproof Coffee could cure.
“It’s really good once you get used to it,” he insisted, and I think we both knew he wasn’t just referring to the coffee.
At this point it would’ve been totally acceptable for me to disengage from this connection. It was, after all, a one-night thing – I had fulfilled my end of the bargain by showing up with a vagina.
And yet I was the one who messaged Geoff afterward, eager to repair not only what was left of our friendship, but even suggested that we give it — us, the sex! — another chance. After a couple of awkward messages later, almost painfully reminiscent of our physical fumbling from the night before, he basically told me, “thanks, but no thanks.” Weeks later, he moved to L.A. and we haven’t talked much since. Will’s and my friendship followed a similar trajectory. We had attempted to come to an arrangement that seemed salvageable, but which inevitably wasn’t and our ten-year friendship ultimately crashed and burned.
I couldn’t believe it. I’d prepped, planned and preened all summer to get these men into bed, men who I hadn’t been all that into in the first place, all for the experience of feeling “the little death,” and I ended up killing friendships, my heart, and my dignity.
Of course not everyone’s one-night stands, or sex-capades, will end like this (especially if you have the foresight to simply use a vibrator). My biggest issue was not that I was a novice but that I didn’t feel empowered by the choices I made; instead I felt disconnected from who I was and what I wanted – not only in bed, but in relationships. The idea of sleeping with someone I didn’t know had always seemed unpleasant and awkward to me; I typically sought safety and stability with my sexual partners. I thought I could cut corners with my heart and hormones by having sex with men I knew on a personal level, but, not surprisingly, the personal got in the way.
The truth is, at that time in my life I was a little lonely, and I wanted to feel good, and these are probably the worst, if not the most common, components of casual sex. Because, in the end, it wasn’t just the sex I craved – but the intimacy and connection of what it meant to be seen and held by another. So I tried to make these one-night stands into something they weren’t – and into something that, if I was being honest with myself, never satiated my physical or emotional hunger in the first place. That’s what made me the biggest noob. Not that I went for the cheap hit of serotonin, but the fact that I convinced myself sex was all I ever wanted in the first place when it clearly wasn’t. The irony of experimentation is that sometimes when we explore outside of what we like, we come to discover just how satisfying what we already like is.
Almost ten years after that summer I was presented with the prospect of a real one-night stand. Let’s call him Jerry. Jerry was a handsome stranger seated next to me at a bar at one of my favorite restaurants in Vancouver. He made a dumb joke about wearing white while eating pasta with tomato sauce, then I made a dumb joke about cacio e pepe being the perfect white-wearing food.
We ended up talking until the restaurant closed.
He was charming, we had chemistry, and he didn’t live in the city. It couldn’t have been a better scenario. No mess, no fuss, just the potential of hassle-free orgasms.
By this time in my life I knew I was the woman who wanted the orgasms and who also wanted the mess and the fuss within the context of a committed relationship. But I thought I was wise enough to know I could handle myself if a perfect one-night stand presented itself. I had learned my lessons and done my therapy. There would be no phone calls afterwards, no sleeping over, no coffee in the morning (shiver!), no fish puttanesca, no impromptu vacation – just no-strings-attached sex with a stranger. An actual stranger. Who I found attractive.
So when Jerry walked me out of the restaurant, I expected to be that woman who could ask for a transactional tryst. After all, I am that woman who’s written countless articles on dating and sex for over a decade now, like, “How to Communicate Sex With Your Body” or “How to Craft the Perfect Opening Line Without Being Cheesy,” or “How to Approach Sex According to Your Astrological Sign” (and, bonus, I already knew he was a Taurus). People still seek my advice on their love lives on how to land the guy, the girl, or the occasional throuple. Now, this was my moment. I should’ve been primed, and ready to go get some.
And yet, instead of licking my lips and jutting out my hips, inquiring about a nightcap or offering to bake him cookies (a classic Taurus treat) I choked, again. This time figuratively.
Jerry looked at me, and I looked at him, and then we had the most awkward pause in the history of awkward pauses. I didn’t know what to say or do. Sure, I liked him. But I liked the idea of what could happen more. I was finally at the age to know there is no such thing as a “sex to-do list” that you must follow. It was always ever about me, and how I felt about myself.
So when he leaned forward…I shook his hand.
I ended our flirtatious evening with nothing close to reckless sex or even a handjob, but instead an awkward (but firm!) handshake.
“A handshake?!” My friend Erica asked, appalled, the following day. “What happened?”
There was only one fitting response I could offer that explained what happened, and why I went home alone that night.
I simply said: “Me.”
Thanks for being here, friends!
As always I would appreciate a like, share, and a subscribe! It means a lot!
Love, Brie xoxo
BRIE LOVES THIS WEEK
Here are some of things I love this week…
💝 Meditating by the water at Kits Beach 💝 Cooking my favourite pumpkin pasta (email me if you want the recipe!) 💝 Tennis lessons in the morning! 💝 Reading a new book (Cult Classic by Sloane Crosley) 💝 Three-hour lunches with new friends, talking about therapy, and growth, and men 💝 Epsom salt baths during the day 💝 French classes! 💝 Zooming with friends (yes, I still do that, and I love it!) 💝 Wearing my New York Mets jacket around town like I know a damn thing about baseball (I don’t!) but the Gen Z kids think I look “sick” 🤭
ALBUM
I’m having a Madonnaissance and this collection is PERFECT. Try not to sing and dance along!
TV SHOW
I’m a diehard Francophile and I love a good thriller/mystery. I don’t know why it’s taken me so long to watch this! I watched all three seasons within two weeks!
PHOTO
I had this lamp in my closet, not knowing what to do with it, and then I saw something on Instagram about having a “kitchen lamp” and I thought it was the cutest idea. It definitely adds a bit of coziness at night and early in the morning. IT’S ALL ABOUT ROMANTICIZING OUR LITTLE LIVES!!
LATEST ON THE PODCAST
Changing your beliefs about being single and celibacy (with Lucy Meggeson)
In this episode we get honest about how powerful our own thoughts are when it comes to embracing being single. For example if you keep thinking being single is shit, then guess what? It will be. But our guest, Lucy Meggeson, is here to help you shift your perspective on your single status by sharing her story. We talk about spiritual awakenings, changing the subconscious mind, living alone, and celibacy!
We GO ALL IN, BABY!
Lucy is a single, childfree, music-obsessed, river-loving, personal growth crazy, autumn and winter-loving, unapologetically passionate, over-enthusiastic, slightly bonkers, recovering perfectionist, daughter, sister, niece, auntie and friend.
She hosts and produces her own podcast, Spinsterhood Reimagined, which celebrates all things single, childfree, and personal growth.
Listen to the episode on Apple & Spotify. And don’t forget to subscribe and review! It really does help get the word out.