"Can I Date Your Ex?"

I've been friends with this guy for a while now and as time passes I like him more and more as something other than a friend. Things would be easy if we could actually date but that isn't going to happen because he recently ended a relationship and I am friend with his ex as well. How do I separate my friendship with him and my romantic feeling for him without hurting our friendship?

Quite the pickle you're in... It's amazing how many people there are in the world and yet we still end up being territorial of the people we've dated.

There is no brilliant solution to this one, but as a general rule of thumb, I think that if your friend is the one that ended the relationship, their ex is free game. One man's trash is another man's treasure. If, however, they had a bad breakup, or your friend was dumped by this guy and is not over him, you need to lay off.

Your situation seems to be a little more complex, though. First of all, you would be catching this guy on the rebound. He's going to need some time to himself before he is going to be ready to start a relationship with you, so I wouldn't rush anything.

Both people need to understand that you're in a tough position because you can't "take sides," but you also have to be completely upfront about your intentions. Let this guy know you're still going to be friends with his ex, and explain to your friend that you have feelings for this guy. The only other alternative is keeping your relationship a secret until things settle down.

Be prepared for one or both to throw a fit for a while, but if they're true friends, they will work through it. It is possible and pretty healthy to have a relationship AND separate friends.