Should You Date Your Friend’s Ex?

What Counts as a Green Light?

Many of us, at one time or another, have most likely been interested in the same guy as a friend of ours. While you two may hash out who gets the cutie you just met at the bar, having the hots for your friend’s ex is a whole different ball game, with the potential of losing both friend and future beau. Here are a few pointers to help you decide whether challenging your friendship is worth the calculated risk.

Friendship Evaluation Time

It’s time to reflect on the depth and importance of your friendship. If this is a friendship of convenience—perhaps through work or a social setting—the risk of loss may be less than that of a long-time friend. You may decide straining the friendship is not worth sampling her ex-boyfriend, or you may choose to go for it hoping your friendship will recover. But this will challenge the friendship, so be prepared.

Pre-Emptive Strike

The minute you decide to pursue her ex, set up a heart-to-heart conversation. Although this may be uncomfortable, she will still feel she has her dignity, instead of feeling like you are sneaking around behind her back. A far worse scenario is her accidentally catching you two together. Even though they’re no longer an item, your secrecy may seem like a betrayal. Give her the chance to get used to the idea and reveal her honest feelings. Unless she is a very jealous person, there is a chance she will come around.

Be the Pillar of Support

Your friend will have strong opinions on the topic, and you’ll want to be there for her emotionally while she works out her feelings. Be supportive of her emotions and listen to her concerns. As long as she is truly over him, she may be able to allow you to pursue him, eventually wishing you the happiness in life you wish for her.

The “Do Not” List

There are certain things to avoid in this discussion! Carefully refrain from comparing the two of you or your compatibility with this guy. This includes comments about intending to succeed with him where she failed, and any dissection of her relationship and where it went wrong. Above all else, do not defend him—as her friend, she’ll need to feel like you’re on her side. There are ways to stand your ground regarding your feelings for him without hurting your friend.

The Roll of the Dice

The question to ask yourself is whether or not you are willing to lose the friendship, since this is a possibility. Hopefully the two of you will come to a supportive understanding regarding this man, and the odds are good if the friendship is strong. But ask yourself if he is worth that risk; don’t go into this unaware of the stakes. Follow your intuition and never lose sight of what your friend means to you, regardless of your feelings for the guy.

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3 thoughts on “Should You Date Your Friend’s Ex?

  1. Sapphire18

    Yes, most of the times it does hurt to actually see your ex dating your friend, but I don’t see anything wrong with it especially when it has been months since the break-up.

    I would, however, agree that it will be bad if you are still trying to make amends with your ex and is trying to bring back the relationship or if not, is still terribly hurting. Most especially when you’re still in a happy relationship with your guy! But if not, and is just jealous since your ex is now loving someone else (be it your friend or not), move on and wait for the right guy to give you all his love.

    I suggest that you don’t look for someone when you’re lonely. I believe that love comes at the right moment. If you guys did break up and couldn’t come around, it just means you’re not for each other. It’s because you couldn’t stand what happened between the two of you.

    This is just an opinion and my point of view. You may or may not take my advice. 🙂

  2. Carmen Knopfette Honacker

    Oh dear, do I have a strong opinion on this one; and I must say that for the first time I disagree with you, Alina.

    It is not EVER OK to date your friend’s ex, period! Defining word here is “friend.” It doesn’t make for a good character if you are sleeping with, or dating someone who broke your friend’s heart. There is no other way of saying it, but if you do that, to me, you are selfish, insensitive and disloyal; and of course, you no longer qualify as my friend.

    There is only one exception to the rule and this exception includes a number of generally, highly unlikely scenarios; such as your friend has happily moved on AND remained friends with her ex. If she can’t stand the sight of him/her, it is absolutely not cool to reintroduce an old wound back into his/her life again.

    Relationships often end because something big has happened, i.e. cheating, lying and definitely heart-break. To make your friend relive that for one’s own selfish reasons is not OK!

    Call it as you may, and I might stand fairly alone with this belief, but my friends’ enemies, people who have hurt them, badmouthed them, backstabbed them and so on, are my enemy too, period. You mess with those I love, you mess with me. For those who think this is harsh, blame it on my Scorpio rising!

  3. Gina Rose ext.9500Gina Rose ext.9500

    It is on the rare occassion, that this idea works out without some kind of hassle down the road…..

    I have seen it work,…. yes, for example,when the first partner actually legally marries someone else , but other than that specific circumstance, 90% of the time not.

    And what if he breaks up with the second partner, only to return to the first partner (?)……I’ve read on that with many clients…..and somebody generally gets hurt.

    Better to try to pass and keep the friendship intact. There are many more fish in the ocean to choose from.

    Blessed Be )O(
    Gina Rose ext.9500


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