When It’s OK to Date an Ex’s Friend (and When You Shouldn’t)

With a few billion people on the planet, is it really so bad that you fell head over heels with your ex’s friend? After all, treading through the often hellish dating world can be tough and stressful, so if you finally find someone you genuinely connect with, does it matter if they happen to be besties with your ex?

Well, yes and no. When it comes to dating your ex’s friend, Gigi Engle, a certified sex educator and the resident intimacy expert at 3Fun, said it will “very much depend on the friendship in question — and the potential relationship between you and the friend.”

While people might have opinions on dating an ex, “it’s not ‘inappropriate’ to date an ex’s friend,” she says. “We all have exes, and relationships end in a host of different ways. If you really want to pursue your ex’s friend and you decide it is the right decision for both of you, hopefully your ex will want you to be happy and not stand in your way. An emotionally mature person isn’t going to have a fit because you’re dating someone they’re friends with just because you used to date each other.”

If you’ve decided you want to embark on dating your ex’s friend — or at least you’re open to seeing how things might develop between the two of you — here are some things to consider.

The questions you need to ask yourself

According to Engle, there are numerous questions to consider before you make the move to begin dating someone who is close friends with your ex.

• On their friendship: “Are the two of them really close friends? Is the ex OK with you dating their friend? Have you asked how they might feel about it? Do you care if they’re upset about it? Does your ex still have feelings for you? If yes, does that matter to you?”
• Your needs: “Why do you want to pursue this relationship? What is motivating you? What do you like about this other person? What would you want to get out of this relationship?”
• In terms of your ex’s needs: “What do they feel about it? If they become upset, why are they upset and why do they have an issue with it? It’s important for them to understand that it actually isn’t up to them — you are no longer beholden to your ex and you don’t have to make decisions based on what they want. They will need to decide if they still want to maintain a friendship with their friend who is dating you, but that’s their battle.”
• In terms of your new love interest’s (the friend) needs: “How important is their friendship? What would they do if their friend told them they didn’t want them to date their ex — would you be OK with that? Would they be OK with that? Are you both prepared to deal with the possible social consequences of this courtship?”
• Should you tell your ex? It might be one of the most awkward conversations of your life, but if you’ve decided to date each other, Engle suggests having an honest and open conversation with your ex, “or have it together with the new partner before pursuing a relationship with their friend,” she says. “You don’t need to ask for permission, but it would be beneficial to at least let them know what is going on, that they mean a lot to you, and you’re bringing them this information because you have respect for them.”

What boundaries should you have in place?

Obviously in a situation like this, things can get a little messy between you and your new love interest and each of your unique connections with your ex. For example, in most dating situations, it’s perfectly natural to bring up your past relationship from time to time but how does that work when your ex lover is best buds with your new lover?

Which is why Engle recommends establishing boundaries in your new relationship. “They could look anything like ‘not talking about your ex’ when you’re together, ‘not talking about your previous sex life,’ to even ‘not seeing the ex at all,’” she says. “What works for the two of you is totally OK as long as everyone is comfortable with the established boundaries. If you feel pressured or coerced in anyway, that is not OK and a big red flag.”

Do what feels right to both of you

No doubt a lot of people will have opinions about dating your ex’s friend, but as Engle puts it, if this is someone you really care about and see yourself with — and they feel the same — a past relationship should not be the thing that stops you from having what you want.

“You have to ask yourselves if you’re willing to do the work and face the social repercussions of putting this into action,” she says. “If you both want to be together, you can make it work. The dust will settle and any ruffled feathers are sure to calm down after some time has passed. I would never suggest compromising your happiness simply because you think dating your ex’s friend is inappropriate. Sure, there are a lot of factors that go into this and it won’t be the best choice in a lot of circumstances, but it certainly can be.”