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If I fuck up with this, it's not just a girl I don't talk to anymore. A family that already gave me their blessing, her older brother is my best friend, and a . Well being your best friends sister, this could go insanely well and result in 

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What to do when your friend is dating a [loser] [drunk] [player] [etc.] this email from a woman who was panicked about her older sister's upcoming wedding: does end up spending 4 years dating a sketchy guy, your friendship will most likely 

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Your friend's older brother may think of you as one of the little pipsqueaks who comes over for sleepovers and watches Disney movies with his kid sister. Stay away from dressing fancy and doing yourself up whenever you go to your friend's house He/she may find it uncomfortable if his/her friend is dating his/her brother.

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