Hey, I'm a 17 year old male who just today, asked a girl who I really like. Oddly enough she said 'yes' but there is one little snag. She is my best friend's sister. I know that if I talk to him that this would probably okay and i know that if he's not okay with this I wouldn't go through with this but how do i approach him about this, should she be there or no? I just need help deciding how to go about this, I don't want to hide this from him at all so soon would be better than later, thank you so much for your advice in advance.
TimothyDanger answered Friday January 9 2009, 7:38 am: She shouldn't be anywhere near you two when you tell him.
If the two of you have talked about girls before, I wouldn't do it... he knows your carnal secrets.
If you have been keeping your conversations about those things pretty PG13.. well I would still tread carefully.
You got to remember that's his sister and he just doesn't see her the way you do, as a matter of fact he may turn a little more watchdog on you as a matter of principle.
miracle89 answered Friday January 9 2009, 5:38 am: i think the best thing to say would be to tell him that you have feelings for his sister, and you really do like her, and tell him that even though you should have asked for his permission first as a best mate to him, you asked his sister to date you. HOWEVEVER, you understand if this would be awkward for him, and that you respect your friendship enough to listen to what he'd had to say.
make sure you also tell him that no matter what happens between his sister and you, you guys will remain best friends.
kristamikele answered Friday January 9 2009, 12:09 am: The best way to approach it is by pretending that you are asking his permission beforehand. tell him that you really like his sister a lot and you want to have his blessing to ask her out, you value his friendship and all that stuff. Let him know that you and his sister might not be together forever, but you promise that you will not do anything to hurt her. remind him that it would be better if you were with her because then he can know for sure that his sister is going to be treated right, as opposed to dating some loser that doesn't give a crap. if he says yes, great. If he says no, well then you're going to have to make a decision. tell him that you're not sure what you're going to do, but you hope that your frienship will be OK regardless. I don't think his sister/your girlfriend should be there because he may feel cornered or act differently, besides, if she is there he will know that the two of you have been going behind his back. In the best possible circumstance he should think that you did not ask her out until you talked to him about it, first. [ kristamikele's advice column | Ask kristamikele A Question ]
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