The Gay Perspective

That is a very complicated question. On paper, the answer is no, but there are always mitigating circumstances.

Let’s assume that you’re single while asking this question, otherwise the answer is a resounding “no.”

Sleeping with an ex is complicated because at some point, you probably cared for each other. And if you don’t want those feelings again, then it’s risky business.

Sometimes it’s hard to disassociate lust and love with an ex, and that’s the reason that – on paper – you should never have the regrettable sex.

Are or were you in love with him, and might sex confuse the situation? Then don’t sleep with him. Are or were you in love with him, and is he in love with you? Then do it, and try to rekindle the magic.

Here is the complicated situation: If you guys are friends, or are at least amicably associated, will sleeping with him complicate the nature of your relationship? This is answerable on a case-by-case basis; there is no one answer to every situation.

If you are looking to get back into a relationship and he feels the same way, then do it. If only one of you is, then don’t jump head first into bed.

There are, however, mitigating circumstances.Is he going off to war? Knock one out for you two to remember each other by in case you never meet again. The same goes if he is simply moving away, never to return.

If there is going to be a seemingly permanent distance between you, then the once-in-love stipulation can be voided. If you guys are both down for it, go for it.

Having sex with your ex-boyfriend, and current friend, is almost always complicated.

The physical relationship inevitably leads to a friends-with-benefits situation, which can lead to heartbreak or relationship woes if one of you starts seeing someone else.

Think about the consequences that might occur, not about how hard up you are.

I don’t want to say to not put yourself out there, but know what the pros and cons of recoupling are before you hop into bed again.