O.k. sorry if this takes a while, but there's sort of a lot to it. I'm sixteen female. I've liked my best friends brother for quite a while, maybe 2 years now, but in the past couple months, about the last 7 months I've Really liked him. It sounds petty but to be honest I've never liked a guy like this, ever. I always thought it was sort of stupid how girls become obsessed with a guy just because he's cute. But, it's not that. And I understand how they feel. Not to sound like a creepy stalker but he's seriously in so many of my dreams I can't help it. He's super quiet, but not in a wierd way, I know there's more to him.. he just has this way about him. He's never had a girl friend, and he's a year older than me. My best friend knows how much I like him.. well actually I don't know if she really knows, she always brushes it off because obviously it's wierd. But every time I get a chance I'll make casual jokes about it, and recently I've done it more and more.. actually.. about a million times in the past ten months. The thing is, I know we'd be perfect, if that didn't sound creepy, but whenever he sees me, which is really rare.. he gives me this smirk, that's really hot. Haha. Anyway, I never see him because when my best friend and I do something together it's usually not at her house but out somewhere, and if it is he's at work. We're both sort of quiet and don't talk to eachother much at all. He's not that type of guy really. So it would be really awkward to say something wierd about how much I like him to his face. And trust me, his sister doesn't want to hear it. So I guess I just want at least Something to happen by the end of the summer. And I know it takes time, but I've been waiting for about a year now, maybe longer. And it's all I can think of.. well sort of. I guess my question or questions is/are, how can I approach someone so quiet, yet really appealing, without it seeming wierd? How can I include him in something me and his sister are doing, without her protesting, and without it seeming odd? And please don't say she should understand if I like him this much, it's not that simple. I guess, how can I get something to happen? Help would be appreciated times a million. Thanks :)!
Jehmehh answered Monday July 14 2008, 3:27 am: I think before you talk to him, you really have to talk to your friend first and make sure she knows and understands the situation. It's awkward for someone to watch their sibling date their best friend. She might be worried that you'll tell her things she doesn't really want to know about her brother, or she'll be concerned that if you guys break up (esp. on bad terms) she'll be stuck in the middle ground and won't know who to help. So first make sure that she is ok with it (she needs to be, she lives with him!) and that you can work out something where she either won't mind him being there, or that she won't be weirded out by you being with him. Also make sure you talk to her just in case there's a reason she doesn't want you with him. She's his sister, so she obviously knows more about him than you, and she might know something about him that you'd be turned off by, or that you should know before having a relationship with him. Also, be serious about the situation when you talk to her, and ease up on the jokes since those only make her uncomfortable anyway.
Now as for him, I know you want something to happen soon but sometimes things take time. Slow and steady wins the race =). But anyway, after you've cleared the air with his sister, maybe try making small talk with him everytime you see him. Just little things here and there to get to know more about him, and see if he shows signs of interest in you. Also, he'll see that you're interested (be subtle about it, not too overbearing) which will help. Then try going out with him and his sister, so he can see that she's ok with the situation, so he should be as well.
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