He is actually my friend too, but I wouldn't know him if it weren't for my brother.  The only time we really see each other (if other than chance around campus) is when my brother, his friend, and me go to concerts together.  I've actually known him since I was in high school because I'd go with them to concerts back then too. I had a "crush" on him immediately but didn't even think much of it since he was a college guy, after all. I have seen him around campus and talk with him. He's only two years older than me. I've randomly seen him in the dinning hall and have eaten dinner with him several times. I got Facebook when I got to college. He was one of the first people to add me as a friend, yay!

There's really no way to know if he's even interested in me. He's obviously not going to make a pass at me with my brother right there. It would get the "dude, that's my sister!" response most likely.

I look at it two ways about my brother: he's either get creeped out I like his friend and possibly not invite me to concerts with them anymore, or else thinks its cool I'd date someone he already approves of and likes. I don't know how to bring it up, "Hey I'm interested in Mike." That would be a bit forward. My brother and I get along surprisingly well for siblings. He's four years older than me so it's just old enough that we weren't close enough to be fighting all the time.  He's the only one I've got and he's one of my best friends. But we never talk much about our personal lives so that's why it would be odd to bring up his friend. Since we are good friends, I'd like whoever I date to get along well with my brother. My only other boyfriend (childhood friend-turned boyfriend) didn't get along too well with my brother.

So what are the rules for dating a sibling's friend? Is it off limits? I don't want to make things weird between my brother and his friend since they're good friends. Any advice?

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ask him out

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^^

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Our deepest fear is not that we are inadequate. Our deepest fear is
that we are powerful beyond measure. Our light most frightens us.