I think you should ask your crush out and find out if she’s interested. If she is, she’ll have to figure out how to talk to her “bestie” about her feelings for you (and really, let’s stop calling this other friend a “bestie” if their relationship involves even one-sided romantic longing).

If your crush doesn’t reciprocate, let her know it’s no big deal and that you hope it doesn’t have to change the dynamics of the group. But … it might no matter what. At the end of the day, people share information with others, and there might be some shifts based on what happens – or doesn’t.

Of course, if you’re unwilling to risk any changes in the group, steer clear of this. But … something tells me the group is going to change anyway. People will date, break up, meet others and join other groups. This is an evolving social structure.

You might hurt someone. There’s no getting around that. Sometimes you’re your own good guy while being someone else’s bad guy, even when you have the best intentions. I’m sure your crush doesn’t want to be a bad guy either, but she’ll have to let someone down if she doesn’t share their feelings.

It’s clear you want to shoot your shot, so do it with transparency and sensitivity, and start with the object of your affection. Don’t involve anyone else in the conversation. This is between the two of you.

– Meredith

Readers? Any way to avoid shaking up the group here?