There is an unspoken code among friends that you just don’t date one of their ex’s. It’s a good code for specific circumstances but for the rest of us, it sucks. If everyone followed this rule there would a lot of happily married couples that never got married. Break ups hurt. A lot. They hurt in ways you never thought they could hurt. Or they don’t hurt at all and you shrug your shoulders and brush yourself off and pull up Tinder on your smartphone. The point is that not all ex’s are the same. Not all break-ups are meaningful and this code isn’t always useful.

That being said, the first point of interest in a situation like this is to give it time. Even if it was a nonchalant type of relationship, jumping right into romance of any type with this girl can make you look like a double jerk. Not only to the friend in question but to everyone else; your other friends, family, coworkers. Gauge your friends recovery time and get a feel for how he’s dealing with it. If he’s been in bed for a week and Jim Beam is his new best friend, it isn’t a good time to hook up with his ex. You need to gauge her recovery time as well. The last thing you want to be is the rebound guy. Read The Signs You’re a rebound guy. If she’s constantly lamenting the lost relationship or even if she just finds a place to insert memories of him periodically, the time is not right.

Are You Planning To Hookup Again?

Your next step is to gauge your own intent. Yes, I’m serious. Decide what you want from this woman and if it is worth potentially hurting your friend and losing the friendship. Let’s say this friend was your very best friend from childhood. He dated said ex for 8 months and you always liked her. She was funny and gorgeous and always had something interesting to say. Time and again you told your friend how lucky he was to have such a cool chick in his life. Then the break up occurs. You see the ex out at a club and she’s the same fun, interesting girl she always was and you two start vibing on each other. What do you want most from this woman? A casual hook up? A romantic relationship? Decide where you’re going with it and weigh it against the potential hazards of telling your friend. Are you prepared to lose the friendship? Are you prepared to get socked in the nose? Only you know those answers.

Who Broke Up with Who Is Important

Another factor to consider is who broke up with who. If he did the breaking up, it is likely to be less painful. He’s apparently thought it out and decided he didn’t want to be with her anymore. Hopefully that means he doesn’t care who she is dating. If she broke it off, it could be another story. There is always the chance that he was treating her badly in the hopes that she would break up with him but if not, and she broke his heart or took him by surprise, there could be a problem.

Do It As Gently As Possible

If you decide to tell him, break it to him as gently and honestly as possible. The most important factor in this whole scenario is that you tell him yourself and he doesn’t hear it from other friends or accidentally run into you two making out at a Phish concert. Sit him down alone and say something like “Ex and I are dating and I wanted to be the one to tell you.” This is about as respectful as you can be without just totally lying and that is not respectful. You want to give him a chance to react to the truth without an audience. It is best to keep details to a minimum. Try to avoid extraneous details at every chance. The most poignant question will be When. When did you start dating? How long after the break-up? One stock answer that always seems to take some of the sting out is “Does it matter? I’m sure any time would have been too soon.” Then make a mad dash for the door. Prolonging these conversations are of no use to anyone. There is a good chance things could escalate and you want to give him time to think.

There really is no perfect time or way to tell a friend your dating his ex. Your only hope is that enough time has passed that he has no interest in what she does anymore. The one thing that will save the friendship is honesty with a large helping of tact and compassion. Do some thinking before you have this conversation and make sure you are saying exactly what you want to say.

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