Is It Okay to Hook Up With a Friend's Ex?
Unless you were a musical theater major (like I was) and thus have no frame of reference for normal interpersonal boundaries outside of your social circle, you likely have some level of hesitation about hooking up with a friend’s ex. Knowing what any true friend should know about a friend's former flame, the ex in question likely isn’t super appealing, is probably really bad for you, and possibly just bad in general. Thinking about hooking up with them doesn't make you a bad person, but not until you really, really give it some thought should you even consider turning those thoughts into action. How you make it work—or don’t—depends on a variety of factors.
One school of thought says you should close that door forever. “My friendships are more important than a new relationship,” says Sierra, a photographer in Los Angeles, who considers the deed to be absolutely off-limits. In a piece for Metro, writer Mike Williams agrees that it’s never acceptable to date a friend’s ex. "It doesn’t matter which way round the genders are—it’s an act that does irreversible damage to a friendship." And again, as the friend of the person breaking up, you probably know too much already, and what you know is not good.
Once you've considered those factors, and hooking up with a friend’s ex is still somehow on the table, there are several things to understand before diving into a Kardashian-level web of potential friendship conflict.
Make sure the relationship is over.
It’s important to verify with 100 percent, iron-clad certainty that both parties are not together, and are completely over the former relationship. Also, it’s essential to acknowledge that regardless if the potential new relationship ends up being a hookup or a full-on dating thing, it’s going to be weird, because there’s no getting around why you both know each other. Be prepared to let the ex-hookup fantasy fade away in order to maintain the friendship. Otherwise, it could get ugly.
It may be okay, depending on your environment.
Depending on who you are and where you live, hooking up with a friend’s ex may not be that big of a deal. “This is not uncommon within queer, kinky, consensually non-monogamous circles—and in some ways is built into the nature of dating within these communities," says Dr. Markie Twist, licensed family therapist and certified sexuality educator. In Cosmopolitan, completely free of prior complication."
Always talk it out.
As for how, exactly, to go about making the friend’s-ex-fantasy thing a reality in the most considerate and respectful way possible, Dr. Twist recommends that you talk to your friend first. Remind them how much you value them and their friendship and do not want to see them hurt. Then let them know you're interested in their ex and, if it is pursued, ask how it would affect them. What would the rules, roles, and boundaries look like? Can you talk about the relationship? Can you all hang out together? Discuss with the ex if the outcome is one you can both live with or if it's a deal breaker.
We're all adults, and at the end of the day, people can date who they want. However, if your friend means anything to either of you, considering how theses things might play out now can save you all a lot of trouble for later.
Be prepared if it ever happens to you.
A few summer ago, I had a life-altering, maddening crush on a woman who wasn’t into me and ended up dating another friend within our circle. As much as it sucked that someone I really liked didn’t feel the same, they’re both friends whom I love immensely, and I don’t own them. They’re ridiculously cute together, and I can’t possibly be mad that a friend fell for my crush just because I liked her once. We’re all still friends, and their adorable love brings me real, actual joy.
As much as it might feel like this person who ostensibly was a significant part of your life should still somehow be yours forever and ever and ever, it’s unfair—and unrealistic—to try and lay claim to someone's future dating life just because things didn’t work out. "I hear this [concern] more from men towards their man friends regarding their female ex-partners," Dr. Twist says. "It tends to sound territorial, and possessive regarding their ex- as if they 'own' who their ex can date." Dr. Twist adds that even though venturing into a sex thing with a friend’s former love interest can end up being “old wine in a new bottle,” jealousy and possessiveness are never cute, regardless of the circumstances.
It all comes down to honesty, communication, and comfort level. Dating a friend’s ex—or an ex’s friend—is a sticky ethical situation, but it doesn’t have to be life-shattering when approached with caution. It could be a disaster and the kind of fantasy that should never, ever come true—or, if it’s done right, totally fine and fun for all parties.
This story originally appeared on Esquire.com.
* Minor edits have been made by the Esquiremag.ph editors.