I want to be with my best friend’s brother

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Dear Meredith,

He is my best friend's brother and we have known each other forever. I have had feelings for him for as long as I can remember. Even when we were really young, we were always texting and doing what I now realize is flirting. However, I never thought he was into me, and I value this friendship so much that I repressed the feelings.

As the years passed, I grew more and more into him. No matter what was going on with anyone else, he always held a place in my heart and we were always talking. As much as I wanted to stop my feelings for him, the more we talked, the more into him I became. How I feel about him is certainly as close to love as I have ever felt. Then, last summer while my friend was asleep, we hooked up. I was elated, but didn't want to tell her about it until he and I were actually together, which won't occur for the foreseeable future because we are in school in different places and  a little too young to be serious about long-distance.

Following our hook up, I made a series of mistakes beginning with inviting my ex to his house the day after and then making out with someone else in front of him at a concert. I didn't mean to hurt him, and honestly I can't even tell if I did because he didn't seem hurt, just kind of mad. Things were kind of complicated for a bit, but we were still interacting and talking all the time because of my friendship with his sister.

By late summer and early fall, we were back to talking all the time, and we even began sexting, as I was back at college. We continued talking a lot right up until I came home for Christmas and learned he had a girlfriend. Throughout Christmas break, he didn't do anything overt, but I could tell something was still between us, and we were still talking, albeit platonically. Now, I'm home again for a bit, and he and the girlfriend are still together. His sister strongly believes that is a relationship of convenience, and I am inclined to agree. He and I continue talking platonically, but being back in the same place as him and not being able to be with him is killing me.

A part of me feels like he and I are meant to be together, and whenever I think seriously about my future, he is in it. I have literally no idea what to do. I'm not the emotionally vulnerable type, but letting this relationship play out without doing anything is tearing me up. Any suggestions?

– A Heartsick Girl


Well, I imagine you're both home for a bit. Perhaps longer than a bit.

This seems like a good time to declare your intentions. At the very least, you can try to be clear about your hopes for the moment. Maybe it seems like your feelings are obvious, but you haven't had much mature communication. After that first hookup, you made it seem like it wasn't a big deal. You made out with someone else in front of him.

If this person is who you want, pause the ambiguous flirting and tell him you wish you could be together, especially now that you're both home and have the opportunity to try. Let him know you've grown up since that concert and that you're a lot more thoughtful these days about how you feel. Also assure him that if he's committed to his girlfriend, you’ll respect that boundary; you just want him to know where you stand.

Also try to leave your friend out of it. You can keep her in the loop (assuming you've disclosed your feelings by now) without making her feel like her brother is all you talk about, or that you’re depending on her for insight – or inside information. Your relationship with her is important too, and you don’t want to make her your spy.

– Meredith

Readers? Disclose? Wait? Stay quiet?