Threesomes Are Great, If You Possess Infinite Amounts of Chill

The one thing no one tells you is how much planning a threesome takes — or how a threesome will fall apart the second you start planning.
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The one thing no one tells you is how much planning a threesome takes — or how a threesome will fall apart the second you start planning.
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The first time the topic of a threesome was ever broached in my bed was all thanks to my own big mouth. I was 23, dating a brooding 30-something screenwriter with delusions of Bukowski, and desperately trying to convert our casual fuck buddy relationship into something more substantial. Knowing my meager sexual history likely didn’t live up to his well-notched bedpost, I did what any girl in my shoes would have done: lied.

Not willing to actually try to keep pace with the kinky specters of his many ex-girlfriends, I knew desperate times called for desperate measures when I sensed John tiring of our fairly ho hum oral-sex-oral-sex-bed by 10:30 PM routine.

“You know,” I purred to him in bed one night after we’d been hanging out for a few weeks, while he was craning his neck to catch a glimpse of Piers Morgan’s guest for the evening, “If you ever wanted to have a threesome, I’d be super into that.”

John and I had some of the hottest sex of our young relationship that night. Better yet, my intended plan had worked: the potential of a threesome was enough to convince him that I was more adventurous than I felt comfortable initiating, while allowing me to bask in the comfort of knowing the logistics of one ever coming to fruition were slim to none. I figured I had signed myself up for a few well-acted apologetic sighs over the next few months at best, as I explained why the bartender at The Woods just wouldn’t cut it for my first, and thus most momentous, ménage a trois. True to my prediction, the threesome barely came up at all again, though it did nudge the door open just wide enough for the pair of us to get more serious about each other.

At the time that this all took place a few years ago, threesomes had become ubiquitous enough that their mention didn’t invoke pearl clutching; yet they were still foreign enough that you couldn’t swing a cat and hit just anybody who’d participated in one. (I went to college in Berkeley so my brushes with threesome propositions had run significantly higher.) Nowadays, we live in a time where being forthcoming about sexual identity is so prevalent, threesomes are far more de rigeur — the tamer cousin to a world filled with butt plugs, cattle prods, and Christian Greys masquerading as a poor man’s Patrick Bateman.

The hardest part of having a threesome, if anyone asks, is everything.

Despite never particularly having wanted to be in a threesome — I maintain to this day that I know 'my crazy,' and relationship-me would be the exact type of woman to go full Gone Girl if I felt even one lick go astray during — I did begin to wonder around the time I hit my late twenties whether a threesome was another life milestone I’d be missing out on. All around me, friends weren’t just sharing their sexual proclivities in a post-Sex and the City universe, they were rejoicing in it. Girls were sending sexts to their group of girlfriends as sexy ego boosts before dates, apps like 3nder — the Tinder for threesomes raised nary an eyebrow upon launch, meanwhile I hadn’t even kissed a girl (and again, I went to Berkeley for college; you had to actively try not to kiss someone of the same sex, that’s how easy it was). So one evening earlier this year, drunk on ouzo and surrounded by a group of girlfriends who’d all approved of a lacy bra photo I was sending to a man I was seeing just moments earlier, I made a teary proclamation.

“Guys, before the end of 2015, I’m going to have a threesome.”

Famous last words. The hardest part of having a threesome, if anyone asks, is everything. For someone born with an extra set of neuroses, a sex act that involves getting to know two complete strangers, both of whom likely already know each other but not me, was a fool’s errand. I knew I unequivocally had no desire to have a threesome with anyone I knew, which left only one other option: being the unicorn in an established couple’s threesome. Or as I liked to call it, “watch two people judge you while you’re naked in an unspoken language they established well before you got there.” So, as you can tell, I was feeling pretty chill about this entire sitch.

“The thing about a threesome is that everyone who’s in it has to be getting something they want,” explained my friend Eric, when I grilled him on how he seemed to keep finding himself in so many casual threesomes.

“For example, I was in a threesome a few months ago with two female friends. One wanted to see if she was bisexual, but had never been with a woman before, and wanted me to hold her hand, literally and metaphorically, through it. My other friend is bisexual, so she was into it. And I get to be around two naked chicks, so everybody won. If someone isn’t getting what they want, you can’t have a threesome.”

Taking Eric’s advice as gospel, I whittled down my list of what I wanted: a nice couple with experience having done this before, perfect strangers for my own mortification factor, and someone who’d be willing to coach me through the experience as well. After many fruitless Google searches of “How do you arrange a threesome?” I turned to my next best option: 3nder.

I cycled through multiple iterations of things a serial killer would say, like “Don’t worry, I’m not a serial killer! Just curious."

While the Internet has made it easier to find people who share your proclivities, it still remains decidedly nebulous on how to pass in those communities as someone who isn’t just a bicurious poser — which was how I was sure I came off as I attempted to craft my overly caveated profile. Having no idea that single people looking for a ménage was the threesome holy grail (in retrospect, the moniker of “unicorn” should have been quite the tip off), I cycled through multiple iterations of things a serial killer would say, like “Don’t worry, I’m not a serial killer! Just curious (About sex stuff, again, not about serial killing).”

From the start, I racked up match after match, and was pleasantly surprised by the couples using 3nder.  Mastering the language was fairly simple after a week or so, and my god, was there no shortage of couples seemingly interested in threesomes. Given that couples both had to have separate phone numbers to create a couple’s account on 3nder (allowing either to respond, rather than having to guess which disembodied voice you were flirting with), I assumed the app was revolutionizing honesty and openness from the start. How incredibly foolish I was.

After 20 or so false starts, I finally found a couple that sounded great: a former Stanford baseball player turned physical education teacher and his very adorable fiancée, a teacher as well. My threesome fears were further assuaged when Aidan suggested hopping on the phone to verify we were indeed who we thought the other was: a call so delightful as we ran through our list of mutual acquaintances, I thought nothing of the fact that his fiancée wasn’t able to be on it due to teaching summer school.

Aidan and I quickly became Facebook friends — mistake number one — and almost immediately, his text messages quickly devolved into one-sided requests for sexting, phone sex, and more, under the guise of “foreplay,” all while imploring me not to mention it to his girlfriend, who he feared would get jealous, while assuring me that she was “just busy, but totally into this!” After an increasingly creepy week with zero responses to my request to speak with his fiancée but plenty of unwanted sexts, I blocked Aidan on 3nder and Facebook with a reminder that if he contacted me again, I would get in touch with his fiancée. (His LinkedIn requests still pop up periodically, which is interesting as “failed threesome attempt” isn’t exactly a category of networking you can select.)

Incredibly put off by the experience but willing to solider on, I kept my swiping thumbs active. A very lovely couple, one who quoted Dan Savage’s sex-positive philosophy of being Good, Giving, and Game and emailed me right away to mention that they recognized me through mutual friends, but were happy to be as discreet as I preferred to be. But they ultimately received the arbitrary cold shoulder from me after one of them happened to “run into” one of said mutual friends; though they made it clear I wasn’t a topic of discussion in any way, both were gifted with immediate blocks all the same.  Potential, hypothetical, imagined betrayals of trust were a significant red flag. Other couples, including any who dared to follow up if I let the conversation drop thanks to my own nerves, fared similarly.

“Well, yeah, most threesomes just sort of happen,” offered up Eric, when I told him how spectacularly I failed. “I know a lot of people who have had threesomes, and none who ever scheduled one in advance.”

Unhelpful advice internalized (if you’ve read this far and believed I was the type of person who ever had things “just sort of happen” in her life, I have a bridge you might be interested in purchasing), I deleted 3nder shortly after and decided to put my goal of participating in a threesome on hold.

Sex acts one taboo are getting more and more mainstream, but the conversations around them are still decidedly harder to engage in — in some ways, even harder than the threesome itself. I haven’t abandoned the goal entirely yet, but at the rate that I’ve been racking up stress ulcers by thinking about it, I have abandoned the idea of event planning my way through it with wedding coordinator-esque precision.

There’s always 2016.

Photos by Uwe Krehci / Getty Images