Is It Ever Okay to Date Your Friend’s Ex?

by Michelle Leigh

Most of us have experienced something like this before: your friend starts dating a really great guy, and you think, “Why can’t I find someone like that? He seems like an amazing boyfriend.” But sometimes things end up getting a little more complicated. Maybe your friend and the guy break up, and then you find yourself actually wanting to be with him. He’s single now; you’re still single. It could be a match made in heaven if it weren’t for one small detail: he’s your friend’s ex. Does that mean he’s completely off-limits? Should you totally forget about him? Is it ever okay to date your friend’s ex?

What are the Relationship Details?

The relationship that your friend and her ex had when they were together is going to be a very important part of answering the question of whether or not it’s okay for you to take a turn with him. How long was the relationship? Was it very long, or just a flash-in-the-pan? Oftentimes, the longer the relationship was, the harder it will be for you to start dating him. But, before you discuss it with your friend, consider what you know about their relationship and honestly assess whether or not it’s worth it. How did he treat her? If he cheated, for example, don’t let your lust fool you into thinking he might be different with you.


What’s Your Friendship Like?

If you want to consider dating your friend’s ex, you need to talk to her about it first. Even if you think you’re going to do it no matter what, you need to at least pretend to care about her feelings. Tell her what you’re thinking and see what her opinion on the matter is. She might not care. If she doesn’t, go for it! It’s okay! If she does care, on the other hand, you’ll have to weigh how important your friendship is versus the positional relationship with the ex. Is he really worth losing your friend over? Your friend is the only one who can let you know if it’s okay to date her ex.

Can You Make It Work?

The way you go about dating your friend’s ex is also going to determine whether or not it’s okay. If the two of you get together, you should make an effort not to make your friend feel awkward, even if she says it’s okay with her. Your new boyfriend might not feel comfortable being around you and your friend at the same time, for example, and you friend might not enjoy being around you and her ex while you’re together, either. The important thing is not to be sneaky and go behind her back. No matter what, she’s going to find out. If you want her blessing, don’t even think about trying to hide your new relationship.

In the end, every friendship is different. Some friends might think it’s never okay for you to date their exes. Others might not care. There is no hard and fast rule, so take an honest look at your particular situation before pursing your friend’s ex.

Photo Credit:  Sbrimbillina

This post was generously provided by Michelle Leigh.

Michelle Leigh is a fashion expert, a self-described fashionista, and experienced dater who loves to share and write about relationships and dating.

4 comments… add one
  • i was just thinking about that few days ago!
    some people become overly sensitive when this happens
    i was about to lose a friend because of this
    thanks for your post 🙂

    • Not fun to lose a friend. Glad you found the post helpful, farouk 🙂

  • I have made it a rule to myself not to date ex’s friends. I cannot begin to say how hard this is to live by – especially if you are really into the guy. This post is great as the only solution could see is to actually talk to my friend about it. I was surprised when I found an ex worth risking my friendship for – and was super stoked when my friend (genuinely) wished me well and are still friends. The ex and I only lasted a year, but it is possible to get the best of both worlds, if you try to!

    • Michelle, thanks for sharing that! It is good to hear a positive story that involved good relationship skills and communication, demonstrating that we can strive for that goal 🙂

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