A Guide To Sleeping With Your Ex

Illustrated by Shawna Huang.
One day soon, you’re going to leave the office at 6 p.m. and it’s going to be dark outside. Not dusky, but pitch-black — and cold. Instead of heading out on whatever adventurous plans you made, you might feel more inclined to just go home and have a couch night with some takeout. We won't blame you: The onset of winter weather often makes the comfort of the familiar more alluring. Relationship-wise, this can be an especially tempting time to revisit past loves instead of seeking out new ones.
The standard dating guidebook has “sex with your ex” in the “never do it” category — you know, alongside "letting the mystery die" and "burping." But, no rule is absolute; there are plenty of times when it can be fun — even healthy — to revisit the flings of the past. Here’s a guide to when and where it’s okay to reopen the ex-file.
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Illustrated by Shawna Huang.
When people say sex complicates things, what they mean is emotions complicate things. Sex itself is pretty simple. So, the ex with whom you moved across the country? With whom you spent nights planning your future mountaintop wedding ceremony? Probably pass. The one you met at a local dive and spent the next two weeks sleeping with, but whose profession you can't quite remember (sales?) — saddle up, buttercup.

"Generally speaking, I wouldn't advise sleeping with an ex with whom you had a serious relationship," says Amelia McDonell-Parry, editor-in-chief of The Frisky. "That just opens up old wounds and sparks drama. But, if there's someone you dated briefly with whom you totally sparked sexually, if not romantically, why wouldn't you have a little fun together, at least from time to time?”

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Illustrated by Shawna Huang.
Moving to a new city is always a little terrifying — especially if you’re past college-age. Often, it inspires aches for familiarity. Instead of hunting for something ambiguous and foreign that you really hope will turn out to be a good thing, maybe now’s an opportune time to defer to a tried-and-true measure. At least, for the time being.

So, if you happen to know that an old fling lives nearby, it’s not the worst thing in the world to say hey. Just make sure you file it under “short-term readjustment strategy.” Anna H., 27, a music journalist, put it like this: “Say you’re lonely, or you've had a terrible day — or that the toilet won't stop running in your new place and you don’t know who to call yet. Calling up your ex to ‘watch a movie’ and maybe gripe about getting lost in a place that doesn't feel like home yet isn't the worst. Orgasms can be a hell of a comfort."

Just make sure that things don’t go past the first week or two. It’s one thing to have a few fun moments as you’re getting your feet beneath you. It’s another to spend so much time on your back that you never get your feet beneath you at all.

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Illustrated by Shawna Huang.
The holiday season tends to be hard for us all. You’re either going home (enough said) or sticking around and watching all your coupled friends disappear. Alongside that emotional shock, you’ve got lots of booze (an easy catalyst for bad decisions), plus, as Sophie St. Thomas, Vice sex columnist, puts it: “Holidays tend to involve travel and more social functions, which can increase run-ins with your past. Since they're landmarks in our cultural calendar, they can be triggering and leave you reminiscing about last year's New Year's rooftop make-out — or rereading lovey-dovey Christmas cards from your ex.”

So, go ahead: Whispering your way through an adult hook-up on your teenage bed is actually kind of fun. Just make sure that, like the wreaths and the mistletoe, everything gets packed up and put in the attic once New Year’s comes.

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Illustrated by Shawna Huang.
When in Rome, eat more gelato. When in Thailand, sit in the back of an open-air taxi with a bunch of chickens like it’s NBD. In other words: When you’re on the other side of the world, a different set of rules apply.

As Katie M., 26, a non-profit worker, told us: “I was dating this guy in the Peace Corps for about five or six months. We split….but continued hooking up every time we'd get together, until we both left Uganda and moved to opposite sides of the U.S. We always had this sexual energy that we couldn't deny, and well, hell — you're living in the middle of the jungle.”

McDonell-Parry points out that this advice pertains in less remote locales, too. "If the two of you happen to be on the other side of the world together — or, more realistically, both invited to the same boring work conference in Scottsdale — and find yourselves having a grand time reliving the good ol' days over overpriced drinks at the hotel bar, no one would blame you for revisiting what each other looks like naked. But, whatever goes down really should stay within the confines of your hotel suite and not follow you back home to your real life — after all, that's where all the reasons you broke up in the first place remain true.”

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Illustrated by Shawna Huang.
Since the time you dated, you both fell in love with other people and then broke up with those people. If you’ve each completed this full wash-rinse-repeat cycle, you’re good to go. In fact, if you've been through enough cycles, you’re like those sweet old folks who meet after 60 years and get married. Forget ill-advised; you’ll be celebrated by the local news.

"If you've been in another relationship since, there is enough of a comparative physical experience...the sex must have been really good [for you] to go back for more. If you've summoned the motivation to get off your ass and properly date...it's usually a good indicator that the relationship is behind you enough, emotionally, [that you can] consider casual sex,” St. Thomas told us. But this, like all ex-sex, is still within the danger zone — so tread lightly. “If you've dated someone else and find yourself still craving your ex," St. Thomas cautions, "it may be a sign of lingering emotions. So, pay attention to your intentions.”
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Illustrated by Shawna Huang.
Should you find yourself faced with a reasonable, honest, and communicative adult person who happens to be your ex — first of all, congrats. Second of all, check to make sure you and your former flame are on the same page. The it’d-be-really-fun-to-have-sex-but-never-date-again page.

"If neither parties are in a relationship or even looking for one, and it is mutually accepted that this is purely for sex and nothing else, then go get your rocks off. But, be mindful of the fact that it could interfere with your ability to move on entirely," says psychotherapist Jonathan Alpert.

“And, of course, if you're going back for seconds, the sex better have been phenomenal in the first place,” adds St. Thomas.

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Illustrated by Shawna Huang.
Even if you’re both in the city where you originally dated, with no serious relationships or mistletoe to act as an excuse, you might just want to go for it. And, that's okay. Just try this first: Picture the two of you lamp-shopping at IKEA, orchestrating a from-scratch dinner, and generally being capital-T Together. Do these images fail to conjure even the whisper of a single butterfly in your stomach? No? Then you’re probably good.

McDonell-Parry just urges caution. “Make sure to keep a close eye on your emotions; if you start to catch feelings, stop.” All of this, of course, assumes that you’re not trying to get together again. If you do notice yourself feeling feelings, and you do want to pursue them, well, that’s maybe okay — but stop sleeping with the person in question, and focus on talking to him or her for a while first.

On the other side of the coin, if you’re feeling nothing romantic whatsoever, St. Thomas reminds us that the basic rules of decency apply. “Be mindful not to let your lack of romantic emotions evolve into a lack of decency; even booty calls with an ex should be met with proper sex etiquette and politeness."

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Illustrated by Shawna Huang.
No matter how "over it" you feel like you are, you should apply the golden equation of ex-sex (a totally real thing): For relationships less than a year long, the ratio of time together to time since breakup should be one-to-one. So, for a six-month fling, give it another sixer. For relationships of two years of more, you can go halfsies (a year apart after two years together).

Or, maybe you’ve got a great reason for ignoring all of these rules. In which case: Have fun.


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