I am interested in someone, but there are some complications and I’m not sure if (or how) I should pursue this hawt, smart, funny, interesting guy.
Here are the issues as I see them:
1) He’s good friends with a few of my good friends, which would usually be a good thing. But he lives with one of them, and their house is the regular hangout for my crew.
2) His ex-girlfriend (who is a cool chick, IMHO) is around a lot and they’re still good friends as far as i can tell. I’m feeling a little insecure, like, “Hey Jane, I want to do many naughty things to your ex-boyfriend. Is that cool?”
3) I’m not sure how to make my interest known while still keeping things relatively casual so that things won’t be as weird if he’s not interested in being more than friends.
I guess it all boils down to: How do I ask a friend out, yet minimize the chance of drama if the interest isn’t mutual?
I would advise you to pursue him only if you really think the two of you would make a great successful couple for at least several months. If you can manage to put your gonads aside for a little while and think about it rationally, then do so. It should be clear to you. If not, spend non-date, group time with him until it is clear.
I think it’s a good sign that his girlfriend still hangs out. It probably means they ended things well. But do look for signs that there is still emotional residue. Because even with no signs, there will be jealousy on her part. Perhaps easily managed, but it’s pretty inevitable.
However, you do not have to check with her before you do anything with him. Your relationship with him, whatever it is, is only between you two. Other relationships are tertiary at best and take a back seat. That includes the other friends. And the house is just a venue.
So my advice to your sum up question: Just put it right out there without guessing games. In a natural conversational moment when you two are relatively alone, ask him if he’s ever considered what it would be like if y’all started dating? Don’t emphasize the sexual aspects of it, since that will likely cloud the discussion. He’ll answer you however he answers you and that should pretty much eliminate drama. There’s not much drama in a thoughtful conversation. During this talk, try to be earnest and not big flirty. You really want to see if there’s relationship elements there, and if not, that’s OK.
I’ve done this twice. It really works and it clears the air in the best possible way. There’s no shame or loss of dignity in telling someone, “I think you are great and attractive. Do you think we would be compatible?”
Men are thrilled to have the weight and worry taken off their shoulders. He may not have ever thought he had a chance with you before. It’s a huge compliment and any guy would be thrilled to hear it from you. Good luck!