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He Said/She Said: Is It Ever Okay To Hook Up With Your Best Friend's Ex?

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When it comes to the best friend’s ex there are two rules:

1) Never hook up with them

2) Only date them.

Our dating experts discuss whether it’s ever okay to date your BFF’s ex:

(Jozen Cumming) HE SAID:

Dating a friend’s ex takes guts, that’s why I always advise people who do it to make sure they’re dating the friend’s ex for all the right reasons. I would never encourage sneaking around behind a friend’s back with their ex, but if you and the friend’s ex are not really going to be in a serious relationship and only want to have some fun with each other, keep that to yourself until the fun wears out. But if you two decide the feelings are serious to the point where you two want to do things like walk in public together holding hands, then it’s time to face your friend and tell them exactly what the deal is.

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The question is not is this right or is this wrong, because that isn’t for you to decide. What you have to decide is how much you’re willing to risk upsetting your friend for the sake of being with someone you feel so strongly about and for that relationship to be misunderstood. No matter how much you say you care about the person who was once your friend’s significant other, your friend is going to see it as an attack.

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I always say, if you’re going to date a friend’s ex, you have to be able to look your friend in the eye, tell them you’re now the new person in their ex’s life, then be willing to get punched in the eye. If you’re not willing to accept your fate, you probably don’t like your friend’s ex as much as you think you do.

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How you break the news is completely up to you. There is no record of there being a right way to say such things, but certainly try not to be insensitive, and don’t force an issue where there is not one. Understand your friend is probably going to be upset and it might take its toll on your friendship for a while, but if you two are really good friends, they will look beyond the fact that the woman you care about is their ex, see her as the person who makes you happiest, and be happy for you.

(Telisha Ng) SHE SAID:

On a personal level I have a strong enough bond and complete opposite tastes of my best friend so I have never come close to even fantasizing about hooking up with an ex-boyfriend of hers. Once one of my friend’s boyfriends is introduced to me, he is automatically off limits and becomes one of the “girls”. I’ll even playfully add an –isha to his name! I have never been tempted by thoughts of, “what if” and I’d like to keep it that way.

Is it ever okay to hook up with your best friend’s ex? Do you want the lie or the truth? The lie is that you are a free agent when single and whomever you choose to lay your eyes on can be yours. The truth is that the decision to choose a romantic conquest over a friendship is something that will impact all parties involved. Even if your best friend were to give you the pass, (assuming there is a discussion) there will be an uncomfortable level of tension in the air for a minute. So the real question is- Are you prepared to sacrifice one relationship for another?

Exes are that for a reason and if anyone has caused any discomfort or pain to a friend of mine, they are pretty much dismissed. I’m no care bear, I’ve dated a friend’s high school ex in adulthood but that’s as far as I go with that because I met all parties in adulthood, so basically there were no emotions lingering.

I highly recommend that you do not keep your intention or current best friend’s ex hook up a secret. Tiptoeing around and loving in secrecy are better left for romance novels, prime time television and rich folks with money and time to burn.

We can think this through, debate, toss it up and flip it but you will never know unless you actually make the move, and I know some of you will- YOLO?

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