Sex & Relationships

Love, Kate: Is It Ever OK to Date a Friend's Ex?

Our new sex and relationship columnist, Kate Carraway, has a few thoughts on the matter


Is it horrible to go out with a guy that my close friend had a relationship with? Their relationship is in the past, and I think I could really like him, but I’m not sure if this falls in the “acceptable” category.

Even this question is one of those friendship stress-tests that you can casually drop into the middle of a group of people and watch them go. off.

An example: if you were my friend, I would say “Ew, no,” not because it’s necessarily morally incorrect on your part, but because I don’t think I really want to be friends with someone who would want to date a friend’s ex. If you were my friend’s friend, who is of the “Everybody Dates Everybody” school, she’d say “How else are you going to meet anyone? C’mon.”

Which I guess is to say “it depends.”

Obvi, it is a definite and absolute no if your friend still has any kind of feelings for this dude, if she’s mentioned him in a sad, yearn-y way in the last six months, if she has any perspective on him and their former relationship other than “Oh yeah that guy! He was cool” or, at the very most, “Yeah, that didn’t work out, which is too bad, but I’m way happier with the motorcycle-stunt-rider cartoonist poet I’m dating now.”

If the friend in question is your best friend, your number-one person, then, it’s unacceptable. If the guy in question was super-super-serious with your friend (or, doy, if he treated her badly), then, it’s unacceptable.

So. It depends.

In some friend-kingdoms, bf and gf status moves as fluidly as a particularly good and soft hoodie; one-off “cheating” is understood more as a party foul than something that recalculates the Google Map of your life. Probably this is extra-true for younger friend groups, or in those extended friend-families that originate in hometowns or at university. If you’re in this kind of situation, I’m sure you have your own social boss/queen-bee type to consult with.

In others, where an implicit or explicit “code” exists, not dating each other’s exes is a basic friendship agreement. Even if you’re sure your friend is over-over-over the man in question (see above re: definite and absolute no’s), it’s still considered skeevy and kind of sad to pursue someone that a good friend has already had emotional realness with, and you probably wouldn’t only be losing your friend, but all your mutual friends, who now have a decent reason not to trust you.

(And, oh yeah: if you’re only into him because he dated your friend, making both of them characters in your own damaged melodrama, don’t date anyone— really—while you pursue some self-improvement/therapy/silent meditation.)

So anyway, your assessment should consider two things: what this decision might do to your friend—will she feel betrayed, maybe even by both of you if she’s still friends with her ex, and is inflicting that worth it?—and what it might do to your friendship. Factor in the worst-case scenarios, not your self-serving perspective of “She’ll get over it, I’m sure.” Are you? Humans are self-protective and responsive to threats; when your “close friends” are the ones doing the dirt—or, perceived dirt—it can feel worse than just about anything.

If you’re comfortable and confident enough to bring this up with your pal before you start even possibly dating her ex, do it. Maybe she’d be open to an extended convo—but you are obligated by the universe, by basic manners, and by girl-code to take the “deep listening” job, to bring the drinks and snacks, and to defer to her digressions and conflicts after you clearly and directly tell her what’s up. You might come out OK. She might be or become fine with it, really—a lot of people just need to be heard and respected to feel normal about something. Or, she might not, and you’ll have a decision to make. But doing any of this secretly will only go badly.

Life is really hard, even when it’s fulfilling and great, you know? Real friendships between women, one-on-one or in babe-communities, are such a crucial source of support and consistency and honesty, and enforce an almost rigorous discipline of showing up for each other. Maybe this impending romance is going to be a great, gigantic love that you couldn’t get from any guy on the planet who hasn’t already dated one of your closies, and will be worth losing a friend over. Maybe not. Which “what if,” and what is actually “acceptable,” is up to you.