Gay Dating Advice

Are Friends Obligated to Tell You They’re Hooking Up with Your Ex-Boyfriend?

Exactly how long should your friends wait before dating or sleeping with an ex-boyfriend? To answer that you first have to ask another question: How long do you wear the veil and play the widow?

As long as it takes. Grieving the loss of a relationship is a deeply personal thing. Some people get over it as soon as they get under somebody else. And other people it takes years.

Your friends should pretty much know where you are in the healing process and act accordingly. If you’ve lost weight, can’t sleep, and start drinking gin like the world is running out of tonic, that’s a pretty good sign he should stay the hell away from your ex-boyfriend.

But of course, it’s never that simple. What if you’re mostly over it but not really? What if so much time has passed that any reasonable person would have healed? That’s when the question of whether or not a friend has the right to date an ex becomes a little bit murky.

The best way to preserve the friendship and have a crack at the goods is to communicate. Your friend should tell you what’s going on. He should tell you there seems to be interest on both sides but that he’s not willing to risk your friendship over it.

He should say something like, “Would you be upset if something happened between us? Your friendship is too valuable for me to feel like I betrayed you.”

Of course, that only works if you respond well to the direct method of communicating. Sometimes it’s better to do it indirectly and gauge reaction that way. For example he could say, “Have you noticed that your ex is flirting with me?” If you get upset, he has your answer. If you don’t get upset, well, that’s an answer too.