Is it time to make my move?

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

We get a lot of letters from people whose casual friend crushes turn into extended periods of unrequited pining. They avoid disclosing their feelings, sometimes for months (or years), and by the time they're ready to ask questions, the answers mean too much. That's why I like to advise letter writers to have these talks sooner than later. Why wait?

Tell your friend that you're wondering whether there's more to your relationship. Let him know you're into the idea, even though you have questions and concerns. The worst-case scenario is that he says no, and if he does, at least you'll feel better about moving on.

Please don't worry about the friend group issue and potential awkwardness, by the way. No matter what happens – whether he leans in for a kiss or leans back to set a boundary – he should want to preserve the group dynamic. Six years is a long time for both of you. This one conversation won't define your entire relationship.

– Meredith