Dating your sister
Setting We went over the visiting/out of town scenario, but there’s more than just one setting where hitting on your friend’s sister is a good idea, and quite possibility the only time such a move will work.
Out of Town It’s going to sound like a complete dick move, I know, but there’s no better time to approach a friend’s sister when she’s outside her comfort zone in a new city, or in a new place, without any of her friends.You’ve known her since you were a pubescent boy and you’ve always sensed an attraction, but never acted on it.Even though she was totally off limits, your hormones couldn’t be controlled and you probably ended up talking about her daily at high school lunch tables and, eventually, outside of parties while smoking cigarettes with your boys.In most cases, bros should be able to laugh about this kind of stuff if they’re in college or in their mid-20s.The time to get pissy about protecting your sister has long passed. Boyfriend What better time to hit on your friend’s sister and let her know how you’ve always felt about her then when she has a boyfriend? First, if the boyfriend gets pissy, your friend can have your back and let him know you were just kidding — no harm, no foul.