Crush on my best friend’s brother

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Meredith,

I'm not sure what to do or ow to explain this, but I've had feelings for my best friend's brother for a while. He's a year younger and I've known him forever because of my friend. We've always been close; we carpooled to high school when we were younger, and we watched movies together that my friend thinks are dumb. We have a lot of similar interests, and suddenly, a little while ago, I looked at him and he didn't seem like just my best friend’s brother – or just a friend.

Recently, we were watching a scary movie, and at one point I looked away from the screen and hid my face in his shoulder, and when I looked up he was looking right at me and I swear we almost kissed.

This is a person I've played family games of Jenga with. I've spent weeks with at the family's lake cabin during the summer, shared inner tubes, etc. And now I keep catching myself wishing it was more. I don't know if I should tell my friend or if I should tell him. Part of me says to tell her because she's my best friend and I've never had a crush she hasn't known about, and another part of me wants to tell him because what if it's all in my head and he doesn't even like me? If that's the case, telling my friend would only make things awkward.

Do I speak up? If so, to whom?

– Crush


My subjective take, as someone who is always worried about her friends: who you tell first depends on your relationship with your friend, and her relationship with her brother. If she's someone who can accept the information without involving herself, why not tell your friend you're exploring these feelings? You can explain you wanted her to know first because she's more important than any of this. You can let her know you'll keep her out of it and do what's necessary to protect your connection with her.

If you feel like she'd want to be left out of this narrative – or that she already knows that you and her brother share your own, private, movie watching relationship – you can silo this information. But really, your letter implies you won't feel good about keeping a secret. The best friend is on your mind too much to do this without her knowledge, I think.

Also, this doesn't have to be a big confession to either of them. You've had so many experiences with this family. Will it be such a shock that you're seeing her brother in a new light? Also, right now, you don't know what you want from him, other than kissing. Don't make any big declarations of an all-caps CRUSH, please. [Insert metaphor about Jenga, where a bold statement makes everything fall down.]

Right now, this is all just a confusing "maybe," and there are no answers yet.

– Meredith

Readers? Who would you tell first, if anyone?