Richard: I think you should do something. Just because he has a girlfriend doesn't mean he's happy. From what you said, they have nothing in common. He's going to get tired of her pretty soon, and with you, he knows what he's getting. Something tells me he still likes you too. I think you should follow your gut and just tell him. I mean, if he rejects you he rejects you, on to the next. But you know you will always regret not doing something, you can't put your life on hold waiting for him to come around because in his book, you will never like him, you have to tell him straight up or else he's just going to date another girl if he breaks up with her. You guys have known each other for a long time, you guys have a strong friendship base, and you guys pretty much know everything about each other. Don't let something like this stand in your way. I know you think it's homewrecking but if they have nothing in common, is it really a "home"? Be smart, Chris. You know what you want, why don't you just go out there and get it?