How to hook up with your brother's best friend?

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I don't know how to make advances without being too obvious. In case he turned me down I wouldn't want it to be awkward. So how would I get him alone? We've hung out once but I thought it was weird and tense so I don't wanna just ask him. Sometimes we ask each other for favors like rides when we don't have a car. Then once we're alone, what would I do? And I don't want my brother's opinion brought up because I'm mostly speaking hypothetically, in case I ever wanted something more with the friend. Not sure I really do I'm just curious.

How to hook up with your brother's best friend?
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