He’s my friend’s brother

What’s been on your mind about your dating/relationship life? Ask your own question. It helps others who are wondering the same thing. Use the anonymous form or email [email protected].

Also, former letter writers, please send me an update! What happened after you wrote in? Did the advice help? Email me at [email protected]. Tell us everything.

Q.

How do I decide if the risk is worth it? I hit it off with a sweet man at a wedding recently. We spent a lot of time chatting, getting to know each other, even texting for a few weeks after the wedding. But he’s the older brother of the bride who is one of my absolute favorite people. We hadn’t yet met before the wedding, despite years of friendship between me and the bride. 

She and I first met after we had moved away from our hometowns and have moved a few times since, so we rarely get to actually see each other, but when we catch up she always speaks so highly of her family, and upon finally meeting them they – he – exceeded expectations. 

I’m interested – and I attempted to subtly let him know – but we don’t live in the same place, have a few years between us, and her friendship is too important to jeopardize. Do I just leave it alone? If not, where do I begin? Who should I be direct with first? 

– Anonymous

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A.

The distance is a bigger issue than the connection to the friend. If it’s impossible to see this man in person, keep in touch and find out if there’s a slow burn over time. Perhaps after many months, it’ll be worth a trip to visit him.

It might be a friendship. It might be more. But if it’s long-distance, there’s no reason to figure it out right this second.

If he’s not impossible to get to (maybe a scenic drive?), ask if he wants to get together. The first hangout can be a fact-finding session. Nobody’s business but yours.

If it seems like there’s romantic potential, you can tell your friend you’re hanging out with her brother. Honestly, it doesn’t sound like she’d be that freaked out about it. Even if you date him and there’s a breakup, you’re all adults. You can tell her you don’t want to risk the friendship, but that you also don’t think one relationship would affect the other, as long as everyone treats each other with respect.

Some people would be thrilled to match their siblings with friends. The blending of chosen and regular family can be a beautiful thing.

But first, decide whether an actual in-person hangout is possible. Again, the biggest barrier is getting there.

– Meredith

Readers? Thoughts on dating the brother of a friend?

What’s been on your mind about your dating/relationship life? Ask your own question. It helps others who are wondering the same thing. Use the anonymous form or email [email protected].

Also, former letter writers, please send me an update! What happened after you wrote in? Did the advice help? Email me at [email protected]. Tell us everything.

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