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This guy is now my best friend and we only met early this year but his sister is unbelievably beautiful and cool. Is it normal for me to try and date her or is that an out of bounds type of situation.
If this is your best friend's sister it's probably best to have a hands off policy. If you're gonna date her only do so if ya'll are actually compatible with one another. If you're only interested in dating her because she's smoking hot and you actually have nothing in common with her then please leave her the Hell alone, if not for her sake then for the sake of your friendship with your best friend. You'd better treat her well, if you disrespect her or hurt her feelings, and end up getting your ass kicked and losing your best friend you'll only have yourself to blame. Make sure your intentions are honorable and tread lightly.
I cant vote either way on this one because I dated my X boyfriends sister although neither of us are lesbians.
It happens. But if you dont think its going to lead anywhere good then be prepared to lose your best friend when the 2 of you break up.
Either do it like RoseIsabella said, like all proper and stuff. or, eventually you'll both probably end up getting drunk and having sex anyway, which is the other way. And you'll both swear not to tell the brother, but he'll find out eventually anyway, and may or may not be openly pissed.
So probably just pretend it's an out-of bounds, but secretly just wait until the time is right for sexytimes.