I'm dating my brothers friend! Haha. It's been working out well so far, nothing is awkward for me. My brother and my boyfriend just don't hang out as much as they used to before, just because he'd rather be with me, and my brother doesn't like being a 3rd wheel (no one likes that).
But yeah, I guess I never thought about it until now. I never asked my brother permission, and neither did my boyfriend. But my brother doesn't seem upset at all by it. But then again, my brother and this guy weren't like best friends forever kind of situation. They had only been friends since a couple months before we started dating. So I guess it depends on the situation.
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Ask your brother if it bothers him. If not keep in mind that if it doesn't work out things will be awkward when the ex comes over.
I dated my sisters friend... it was weird the whole time because she was always talking about me to my sister... just strange. I also dated my friends sister... also weird.
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