9 Tips for Dating Your Best Friend’s Ex

The short answer to the question of whether or not you should date your best friend’s ex is a simple NO. But then, love is anything but simple. Planning on jumping in anyway? There are nine important things you should consider before you land yourself in the deep end…

1. Make Sure It’s Worth it

Due to the risk of losing a friendship over dating an ex, make sure that the union has potential and is worth the gamble.

2. Make Sure it’s Over

There’s nothing worse than stabbing your fork into a love affair that is still warm. Often, towards the end of relationships, couples do a little pre-shopping. Make sure you’re not playing the part of a cashmere sweater heading into the dressing room for a trial fit.

3. Give it Some Time

Once the relationship is over, the standard waiting period is either slightly longer than the couple was together or six months, whichever comes first. Don’t jump the gun too soon, or hard feelings will be the end result.

4. Friend Loyalty

The old saying goes, “bros before hos,” and when it comes to dating an ex, you’ll want to be sure they’re genuinely okay with it. You may ask permission, but pay the most attention to the way they answer the question, than the words that come out of their mouth.

5. Have the Talk

While it may be easier, it’s asking for trouble to go out with an ex, see how it goes, and decide to tell your friend based on the results of the first few dates. Suppose your friend sees the two of you, or someone else does. Most likely they will be okay with it. However, if they aren’t, ask them why. You might be surprised to find they’re more concerned about your welfare, than their own.

6. Talk With the Ex

It’s amazing how many people have stepped past the friend zone with a friend’s ex, without even talking about what they are actually getting into. You may have decided a relationship is worth the risk, but until you hear what the ex has in mind, you might be as well be a one night booty call.

7. A Simple Thank You Will Do

If your friend agrees to a date with their ex, offer them a heartfelt thank you for their understanding. Either way you look at it, it takes a big friend to look past any hurt feelings to the happiness of a friend. By sharing your appreciation, regardless of what happens, it will be less likely that they will develop hard feelings later on.

8. Avoid Comparisons

Sooner or later, the thought is going to cloud across your mind, I wonder how I am in comparison to them. Considering that you most likely were privy to some of the information dished out by your friend, you’re going to be armed with enough to question the value and longevity of your own relationship. Resist the temptation to measure up to your friend’s experience, and just enjoy your own.

9. Keep it On the Down Low

Your friend might seem like the most helpful person to share any problems you’re having with their ex, but it is highly advisable to keep things on the down low. Not only could their opinions cause you to make a hasty conclusion, they may also casually introduce several new concerns from their own experiences. Most importantly, never gloat about succeeding where they failed, even if they seem okay with things.

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13 thoughts on “9 Tips for Dating Your Best Friend’s Ex

  1. Possibly

    People are people and relationships are relationships. Should one take precedence over another?
    Every situation is different not to mention the people involved.
    While there may be billions of people on our planet, each of those peoples personalities fills a niche of sorts, the significance of the niche to the parties involved should determine the relationship possibilities.

  2. crista

    In my oppinion dating your bestfriend’s ex might ruin your friendship, be careful because he might be using you to make your bestfriend jelous or ruin your friend ship..

  3. Yessie

    It hurts my best friend is dating my ex and she knows I still love him he broke up with me and his best friend broke up with her at the same time and I guess they are doing swicharoos but it hurts so much I wish she could just understand I’m not mad at her it’s just I mad at the fact we made a promise to never date our ex no matter what I don’t know what to do ?

  4. Valerie Stewart

    I’m having trouble with this at the moment, I have feelings for my best friends ex but his best friend is also my ex. I know the rule ‘you shouldn’t date your ex’s best mate’ and ‘you shouldn’t date your best friends ex’, I just don’t know what to do. Although my ex is the one who ended it and has already moved on, and my best mate was the one who ended it with her ex, I’m still not so sure. Apparently my ex is still a little guilty for ending it, and my best mate and her ex are still spending so much time together. I know he still loves her, he talks to me all the time about it and my heart breaks a little every time. I just can’t tell him. I don’t know how to. Plus he sees me as the ‘kid best friend’ who dated his best friend, and I just don’t know what to do.
    What’s worse is that my dads side of the family is really close with his family, since we’ve know each other since I was 7 and he was 9. I’m now turning 17 this year and he’s turning 19. He finishes year 12 soon and I don’t know what to do. Help? :/

  5. Sasha

    Hi, I kinda like my bestfriends ex, but he is also my ex too… But I don’t know whether to tell him or her that I like him or just to leave it.. But I know she still likes him and i don’t want to be a bad Friend help?

  6. Amber

    A friend that dates your ex behind your back is not a friend. If you are dating a ‘friend’s’ ex than just know that you are not a true friend. Stop talking to the ex and the ex friend because it’s not worth it to be around people that are not respectful or considerate of you.

  7. Julia

    I am dating my best friends ex… She didn’t take it very well! She called me a backstabber and doesn’t talk to me anymore. She use to try and forgive me but not anymore. I don’t know if I should give up on her or keep trying?…Any suggestions?

  8. nick

    i have just asked outmy best freinds ex and she has saaid yes my best freind dosent know about this yet and they just broke up 3 weeks ago waht sould i do i think i should tell him tomorow but what if he doesnt understand

  9. jenni

    My best friends is going out with my ex, who I still have feelings for. She asked my permission and I told her she should say yes because I wanted to be a good friend but it truthfully hurts a lot seeing them together. It brings back memories of when he used to say he loved me and it was only a few weeks ago so that’s pretty tough to. I hate when she tells me how adorable she thinks he is or how happy they are together, I know I should be happy for her but it’s just really hard..

  10. Rose Cocca

    right now im not dating any ex…i like to ,know that im dating one….if he goes back to his ex..then that mean i am nothing to him…and he doesnt care for me as he used to…

  11. Gina Rose ext.9500Gina Rose ext.9500

    These are very good tips…..

    …but I have to say, I have YET to see , or read on, a situation where dating your best friend’s X doesn’t turn into a mess in the long run.
    I do many readings on this subject and either your best friend WILL be upset over it …OR….he/she breaks up with you to go back to their X.

    It’s just not worth the hassle and hurt feelings.

    Blessed Be )O(
    Gina Rose ext.9500


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