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I saw her walk across the hallway and knew she was in my brother's room. cuz I don't really care anymore ever since they started dating. My best friend like my brother and my brother like her is it ok to tell her its ok to date him are is it a line that she just shouldn't cross she cool and so is he but my. My brother is 18 and my best friend is Sure I guess I'm happy that their happy but I mean they haven't told my mom and they hid it from me. I'm going to warn you right now that dating your best friend's brother is probably a bad idea. Things can get messy fast and it becomes really. The more you know about your friend's older brother, the Talk to him about dating in general. For example, you could say something like, “So, Tommy, what do you think makes a good relationship?