Well my sister is 2 years younger than me but her best friend is HOT. Would it be creepy or weird to try to pick her up? I don't know how women feel about this type of thing.

Yikes.
I wouldn't touch it.
First off, she's your sister's friend. That girl's knowledge of how gross you are is second only to your mother's. Sisters know things and what they know, they share. and friends are the go-to spot for all things 'My brother is SOOOO gross'.
Secondly, She's your sister's friend. Girl's think of their friends as sisters they never got to have. So this isn't going to look good to your sister or her friend.

I'm not saying don't, I'm not saying I know best, but I am saying that it looks an awful lot like a big snake pit of 'No'.

Cinnamon

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Yeah that's what I figured. Thanks.