Hi Meredith, I have feelings for a friend from college. He's a great guy, works hard, and is definitely a catch. I’ve known him for six years. Two problems: he's a core part of my main friend group in the city, and he dated a mutual friend for a long time. (I'm not close enough to this mutual friend that this issue alone would stop me, but it's still something that adds to the complication.) Our friendship is definitely flirty in nature, but I can't be sure how he's feeling. He's made drunken comments to me in the past about wanting something more than just friendship with me, yet when he's sober he's made a point of saying that he doesn't want to date from our friend group again. I'm 26 and don't want to wait several months (or longer!) just to be disappointed if nothing comes of this, but I also don't want to ruin our friendship and the friend circle if I say something to him and it turns out he's not on the same page. Do I take the chance and make a move, or should I move on and try to get over it? Thanks for any help on this matter. ----A Classic Situation