The Ex Factor: Should You Date A Friend’s Ex Or An Ex’s Friend?

Should you date an ex’s friend? Should you date a friend’s ex? Should you date someone you know your friend was once interested in, but never dated? As if dating wasn’t complicated enough (especially if you live in a city or region where everyone knows everyone), there are so many stipulations on the moral front when it comes to right and wrong in the dating scene. But does it have to be that way?

Most of us have found ourselves in some sort of sticky potentially romantic situation at one time or another, forcing us to choose between what we feel is the right thing to do, versus taking a chance on what could be a great new relationship. This can be viewed two ways:

1.)  Most relationships don’t end in marriage, so it’s really not worth going down that road to potentially ruin a good friendship.

2.)  The relationship did not work out with your friend and their ex for a reason, so why not ask your friend for their blessing and see if you two are a better fit?

I believe in the latter. I have seen a few guys get bent out of shape when one of their buddies decides to hang out with someone they used to date. When this happens, they often weren’t even in a serious relationship with the woman, but got mad at the friend anyway, saying the friend broke “the guy code.” They also get mad at the woman they once dated for accepting the offer from the friend to get together. From a personal perspective, I’ve been the woman in this situation. A friend of an ex I briefly dated asked me to get together; I wondered if he knew I dated his friend. He must have known; they were such close friends! Still, it’s easy to find yourself in these situations in NYC as people date a lot and don’t necessarily talk about every date they go on if it’s not that serious. And if you’re attracted to a certain personality type, there’s a good chance you could find yourself attracted to the company your guy keeps.

In a world where it can be so difficult to find “The One,” I don’t think there should be any rules when it comes to love. If a relationship didn’t work out between you and someone else, and you know your friend is interested, I don’t see the point in getting angry at your friend for seeing something in your ex that you may not have seen. As long as he or she wasn’t strategizing a way to break up the relationship while you were dating, wouldn’t you want your friend to find happiness? Even if it’s extremely upsetting that they may have found happiness in your ex, I would say it just wasn’t meant to be for you two. The bright side? You could have been a catalyst in helping them find their b’sheret!

If someone asks you to go out and you know they are good friends with someone you may have dated, or with whom you’ve been intimate, go for it anyway. Just consider whether or not you should ask the new person if they know you dated their close friend. My advice? Just get to know each other and take things slowly until you find out their true intentions. If their intentions are of a casual nature, you may not want to move forward, considering the close connection. However, if the relationship has the potential for more, you can always talk about it down the line. However, if you had anything significant with the ex, and they are good friends, that new person likely already knows. If the ex never spoke about you, then there couldn’t have been much there for him to get mad about. So regardless, when it comes to love, take chances, because like Leo Buscaglia said, “Love is life. And it you miss love, you miss life.”