July 31st, 2013 by Jess Downey

On Dating a Friend’s Ex (And Handling It Gracefully)

Photo by xeeliz (Flickr)

Photo by xeeliz (Flickr)

When you’re single and all of your friends are single, it’s not that uncommon for you to crush on the same guys as them. But what happens when the person you’re interested in is your friend’s ex? Should you date him/her? And if you’re dating a friend’s ex, how can you can you handle it gracefully?

It’s a tricky situation — some say it depends, some say no way. But me, I think it’s OK to date a friend’s ex. And I feel this way for two very good reasons: it didn’t work out with them for a reason and if your friend is really your friend he/she won’t deny you happiness.

Now, before you go crazy on me, let me say that I was actually in this situation before. My friend’s ex boyfriend wanted to date me. I talked to my friend and she said it was perfectly fine. Actually she practically pushed us together. We dated for a little while, but once things started to click she apparently decided she wasn’t OK with it and started to sabotage things.

So, I know it’s not as simple as just saying sure, go ahead and date your friend’s ex. It’s a complicated situation. But it doesn’t have to be something that totally ruins a friendship if you handle it correctly. Here are a few ways to handle it all gracefully.

Be honest (about everything)

If there is a mutual attraction between you and your friend’s ex, be honest with your friend before you act on it. It doesn’t have to be dramatic; mention it over drinks or dinner. Trust me, your friend will appreciate it and it shows that you value what the two of you have (and that you respect him/her).

When your friend comes to you with attraction for your ex, be honest and voice your concerns. No matter how bad or crazy you might feel. Talk it out and figure out a solution that makes all parties as happy as possible.  And, if you start to feel squeamish when they’re dating, address the problem head on or give it some time rather than totally sabotaging their new thing together.

Be accepting

Accept that it might be a little weird if your dating a friend’s ex. Also understand that it might take a little while for your friend to adjust, so be gentle and try not to rub the gushy love stuff in his/her face.

On the flip side, if your friend decides to date your ex, accept it. Don’t put limitations on what they can or can’t do. And don’t convince yourself that this will just be a fling or won’t work out since you guys didn’t.

The bottom line

Having a boyfriend is more important than friendships, but I also don’t think friends should stand in the way of another friend’s happiness either. It can feel like a no-win situation, but at the end of the day, I believe if a guy comes in between two people then you probably weren’t that close to begin with.


Jess is a freelance writer and online columnist living in New York City. She recently got engaged to the man of her dreams (whom she met online, of course!) and is always eager to share her online dating tips with the world.

One Response to “On Dating a Friend’s Ex (And Handling It Gracefully)”

  1. August 05, 2013 at 7:53 am, SarahJ said:

    Hi Jess, I agree with you. This kind of happened to me to. I started dating my boyfriend after he had a short fling with my friend. I intorduced him to her with no intent to hooe them up. I told her from the beginning to stay out of it, as he was coming after a break up of a more serious relationship and he wanted to have some fun and she wanted the true big love…
    Anyway, they had this short fling, they broke up as they didn;t want the same thing and after some time he become closer to me, as he was my friend for some time, and one thing led to another…we fell for each other as we;ve always like one onother.
    And the thing is, although my frined told me in the beginning it’s ok to date him, as they were just a one month fling, she started to act wierd and she starterd to be mean to me as my relationship with him was getting more and more serious. I understood it was jealousy and we started talking less and less. Than after more then half a year she admitted she actually did have a problem with me having a serious relationship with him and him not wanting to have that wth her one year ago…So things were complicated. I was upset becouse I was honest with her and she wasn’t. She never told me what she actually felt and made me believe she was ok with our relationship but actually she was very angry with me.
    Although I do regret my relationship with my friend is kind of over, I don’t regret starting the relationship with my boyfriend, becouse we make eachother happy.

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