Well, all valid points. You have known her for a decade and she's a best friend, so I suppose the relationship aspect is already there. And alcohol is certainly a social lubricant, so it could make you more relaxed. Just...be sure that's what you want, particularly as far as the alcohol goes. What seems like a FANTASTIC idea while drunk isn't always what we'd do while sober (trust me ). It only happens the first time once. As long as you're comfortable with the idea, I don't see the harm...just make sure that booze isn't the deciding factor between yes and no.