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anonymous
writes: I have strong feelings for my best friend's little sister. They don't live together and she's 2 years younger than me. We flirt a lot and we enjoy each other's company but if I ask her out I don't want to ruin my friendship with my best. I dont know whether to ask him first or just ask her out and let him figure it out. -confused male 14
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male
reader, anonymous, writes (16 March 2006): my mate's sister is mind numbingly hot, and ive also known the family for a long time, our dads went to school, honestly i get along amazingly well with her, but now we've moved into the friendship zone, she actually told me she loved me and then followed it up with three of the worst words in existance "like a brother".
trust me, you dont want that
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male
reader, anonymous, writes (28 November 2005): Im in the same situation. I have known my best friends sister for many years and only recently has she held my interest. I talked with her 5 min. ago about it and we are going out thurs. So, i asked her casually if her father would kill me (mentioning it because we have good family relations) and she suggested No, but however, her brother (my BF), would wanna kill me. Here we are; the date is set and i feel uncomfortable...not to mentions she's still in h.s and i'm a senior in college, and my girlfriend i'm sure would not approve. I'm certainly not going to tell my gf, that would be apparent suicide, but i think im going to make a light comment to my BF like: "i wonder how many meatballs i can stuff into your sisters mouth? i'll let you know friday because im taking her to italian on thursday". Wish me luck, i would hate to lose a friend over his hot sister...but we live and learn.
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reader, anonymous, writes (1 April 2005): Well, put it this way: hint around it, like say, "what if some dude liked your sis?" Ask your friend what would he think and if he seems OK with it, then ask him what he thinks about you and his sis. And if he's fine with it then do it. If he ain't so fine with it, talk to him about it. See why he isn't, then try to like talk him into it. :)
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female
reader, Bev Conolly  +, writes (13 March 2005):
 Why not invite your mate and his sister out with you together? The three of you can have fun and you can also get to know your mate's sister a little better, before you decide if you want to go out with her on her own.Then, if you decide you DO want to ask her out, you'll be a little more confident and have more to talk about with her.Let your mate put 2 and 2 together on his own. Unless you're a complete beast - and I'm sure you're not - you wouldn't do anything to your mate's sister to affect your friendship with him. And he doesn't "own" her, so it's not really any of his business anyway. He'll work out the details on his own, but if you really feel uncomfortable with it, mention it to him in passing after she's agreed to go out with you, as in "Did I mention that your sis and I are going out next week?"Good luck!
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