When to Date an Ex’s Friend (and When Not To)

With a few billion people on the planet, is it really so bad that you fell head over heels in love with your ex’s friend? After all, traveling through the often hellish world of dating can be difficult and stressful, so if you finally find someone you’re genuinely connected to, does it matter that they happen to be best friends with your ex?

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

While people may have opinions about dating an ex, “dating an ex’s friend isn’t unacceptable,” she says. “We all have exes and relationships end differently. If you really want to woo your ex’s friend and have decided it’s the right decision for both of you, hopefully your ex will want you to be happy and not get in your way. An emotionally mature person won’t have a tantrum because you’re dating someone they’re friends with just because you’ve dated each other before.”

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

Questions you need to ask yourself

According to Angle, there are a lot of things to consider before you start dating someone who is a close friend of your ex.

  • On their friendship : “Are they really close friends? Does your ex agree that you’re dating his friend? You asked how they can relate to this? Don’t you care if they’re upset about it? Does your ex still have feelings for you? If yes, does it matter to you?
  • Your Needs: “Why do you want to continue this relationship? What motivates you? What do you like about this other person? What would you like to get out of this relationship?
  • In terms of your ex’s needs: “What do they think of this? If they get upset, why are they upset and why do they have a problem with it? It’s important for them to understand that it’s really none of their business – you no longer owe your ex, and you don’t have to make decisions based on what they want. They’ll have to decide if they want to still be friends with their friend who’s dating you, but that’s their battle.”
  • In terms of your new love interest’s (friend’s) needs: “How important is their friendship? What would they do if their friend told them they didn’t want them to date their ex? Do you agree with this? Will they agree to this? Are you both prepared to deal with the possible social consequences of this courtship?
  • Should you tell your ex? It can be one of the most awkward conversations you’ll ever have, but if you decide to date each other, Angle suggests that you talk honestly and openly with your ex “or spend it together with a new partner before continuing with their friend,” she says. . “You don’t have to ask permission, but it would be helpful to at least let them know what’s going on, that they mean a lot to you, and you’re giving them this information because you respect them. ”

What boundaries should you set?

Obviously, in such a situation, the relationship between you and your new love interest, as well as between your unique ties to your ex, can get a little confusing. For example, in most dating situations, it’s perfectly natural to reminisce about your past relationship from time to time, but how does it work when your ex-lover is best friends with your new lover?

That’s why Engle recommends setting boundaries in your new relationship. “They can look like ‘don’t talk about your ex’ when you’re together, ‘don’t talk about your previous sex life,’ or even ‘don’t see your ex at all,'” she says. “What works for the two of you is perfectly fine as long as everyone is comfortable with boundaries. If you feel pressured or coerced in any way, this is not normal and is a big red flag.”

Do what feels right for both of you

No doubt a lot of people will have opinions about dating your ex’s friend, but as Angle puts it, if it’s someone you really care about and who you see yourself with – and they feel the same way – a past relationship shouldn’t be the one that stops. you from having what you want.

“You have to ask yourself if you are ready to do the job and face the social consequences of putting it into practice,” she says. “If you both want to be together, you can do it. The dust will settle, and the ruffled feathers are sure to settle down after a while. I would never advise compromising your happiness just because you think it’s inappropriate to date your ex’s friend. Of course, there are many factors that go into this, and in many circumstances it won’t be the best choice, but it certainly can be.”


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