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Is it wrong to date your friends sister? It's not, but this is how I would like it. Whenever a guy in my office liked a person's sister, I had a protocol. Always go to him first and say, "Hey John, I just want to let you know, I really like your sister. Would you have a problem if I asked her out?" If he's a comfortable guy, he's gonna say, "I respect the fact that he came up to me." If he's gonna come and be a jerk to you, he's gonna be a problem no matter what. You already know that. Well, what if he says no, but I like, I love this girl? Then address it. John, I'm saying this to you respectfully, but I'm gonna ask her out regardless. But I just wanna give you the respect that I'm pursuing her and I wanted you to know first. Because if I find out afterwards, I can't trust you. All you have to do is ask me. If you ask me, then we're good. You don't ask me, now I can't trust you. Clear communication is important.