Well, at least you understand the reasons it could be a problem. The biggest would be messing up your brothers' friendship with this guy. The other would be having to run in to him and hear about him if things do not work out. I am not a big fan of a girl asking a guy out. He should ask you out. Maybe the one brother could feel that out with the guy and see if he is interested. That guy may be having fun flirting but not ready to risk p*ssing off his buddies if things do not work out with you. And honestly, most guys don't know right up front how they feel about you. They do know if they have a physical attraction to you, but as far as whether they are ready for a relationship, that takes time and dating. It may be too much pressure for him to try and date a friend's sister because, well, what if you have sex and then he decides that is as far as he wants to go. Or he decides that he doesn't want to date you anymore, he may worry that your brothers will be p*ssed. Maybe the one brother knows things about his friend that makes him feel this guy is not the best for you, who knows.
ouch.. three brothers that's tough! well if your bros are cool with it then I don't see why not. Give it a shot. What I would do is talk to the brother that seems to have a problem with it. Maybe if you pull him aside and tell him how much you really like him, he might respect that and be okay with it.answer mine?... link
Can I date my brother's friend?
I have three older brothers who have all been quite overprotective while we were growing up. Now they are just overprotective when it comes to their... Show More