Is It Possible To Date Your Ex's BFF?

Photographed by Rockie Nolan.
There's an episode of Seinfeld in which Jerry falls for the roommate of the woman he's seeing, leading him and George to try and work out whether or not Jerry could make The Switch. "Do you realize in the entire history of western civilization no one has successfully accomplished the roommate switch?" George asks Jerry. Nevertheless, the two put their heads together and work out a plan which, sadly for Jerry, inevitably fails.
But this question doesn't just make for good sitcom fodder. It's one that has likely popped up in the minds of anyone who has met a partner's friend with whom they hit it off. So the question lingers: Can you pull off dating someone who is close to your ex?
The answer is, of course, complicated. "It depends on how long you two have been together, how close of friends they are with the other person involved, and what kind of relationship you guys have," says Kristy LaRocca, a psychotherapist in NYC. "If you and your partner aren't in too deep, it might be easier to make the switch." It makes sense — if two people haven't been dating all that long, and intense feelings haven't developed, the person being "dumped" might be totally okay with their former partner dating their friend, and minimal drama and awkwardness will ensue.
The fallout might also be minimized depending on how you and your ex approach dating in general. "If you and your partner are polyamorous, the transition might be a little easier," says Jesse Kahn, LCSW, the director and supervisor of The Gender & Sexuality Therapy Collective in NYC. This was actually the case with a couple he once worked with. "They were one another's primary partner, but both had the feeling of, 'If you left me to pursue a primary relationship with someone else, even though I'd be hurt, I'd also be happy because I'd know your needs were being met better by that other person,'" he says. "In a lot of poly relationships, partners can be extremely excited if their partner falls in love with someone else."
That, of course, is a unique circumstance that not everyone is going to relate to, so there are a few things to keep in mind. "You might have to end up cutting contact with the first person because they're upset over what they perceive as a betrayal," LaRocca says. "And while that may be easy for you, the relationship between your partner and their friend may suffer because of it." The friend may feel like the dissolution of their friendship isn't worth a potential relationship with the other person — and it's important to be mindful of their feelings.
Another wrinkle, according to Kahn, is that rejection tends to sting more when someone else is being chosen over us. "Knowing that someone else was a better fit for a person hits harder," he says.
So, while Jerry and George's plight might not be impossible, it's definitely filled with minefields — so expecting to get out of the situation without a little tension is wishful thinking. "Anything is possible," Kahn says. "You just have to figure out if the ends justify the means."