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9 years ago I met this guy at school and we became best friends.   He is like a brother to me, and sometimes I feel that he does more for me than my actual biological brother!!!   I've to his house a lot of times - studying, playing xbox and stuff like that and he's been to mine as well.   In other words our friendship looks like something perfect.   His family has always been nice to me and his father actually told my father that I'm like their son to them as well.

The "problem" started around 2 years ago when I started seeing his sister in a different way...   I started to develop feelings for her.   She's 18 (and I'm 19):   I knew her since she was around 9 or 10 and like I said, we basically grew up together.   There is a friendly relationship between us, even though it's not as strong as the one with her brother.

I decided to tell my friend everything, for I wanted to be honest with him.   Of course, you can imagine how awkward this discussion was.   I told him everything - how I feel when I'm with her, how she makes me laugh, how I like how her eyes light up when she's laughing.   His reaction was as I had anticipated... he told to wait a bit because she was a bit young (she was just turning 17 and I was already 18), and he told me that maybe one day we'll see.   And that was that, he never mentioned this ever again and we went on as if nothing had ever happened.

I tried to go out with a few more girls after that, but none of them ever felt right.   All I can think of is her.   Whenever I'm at their house and she's there, it seems like everything stops (like a slow-mo romantic movie) and it's just me and her.   We haven't been on an "official date" yet, but we've hung out a few times.

My problem is, do I tell her directly?   Do I tell her "Hey, listen, I like you..."?   Obviously I afraid of being rejected, and also, I don't want to ruin the relationship I've built with her already or the relationship with her brother (my friend) and their family.   Sometimes I do give her a few hidden hints, like complimenting her and being super nice to her, but she doesn't seem to notice any of these.   I even bought her a bracelet for her birthday this year and she loved it a lot.

I've considered sending her a letter, telling her everything and that if she likes me she'll tell me, but if she doesn't then she'll go on as if nothing happened.   I know that's a bit cowardly but I really can't take it anymore - my heart feels tattered and I keep thinking of loosing her once and for all.   What should I do?

Anyway thanks for your help and sorry for the long post.

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Well that's quite a complicated issue. First we need to assess your friends opinion on the situation. The connection between brother and sister is usually very strong even if they fight all the time, but your friend and his sister are still two different people, they shouldn't be dictated by the other's opinions. How protective is your friend of his sister? If he has taken the position of -if you hurt my sister then you're dead to me- then it's a bit more problematic, but if he thinks his sisters romantic life is separate from his life (which it should be) then it'll be a lot more easy.

If he is incredibly protective then you'll have to decide what's more important to you, a definite and strong relationship with your buddy or a semi-likely and not-as-strong relationship with his sister. In this scenario don't let your libido ruin what you've spent so long building up. It isn't 100% certain that she'll love you and it isn't 100% certain that it'll last either.

If he isn't so protective then you can quite easily attempt to flirt with her and talk with her. If your friend has been with you for 9 years then he'd probably recommend you anyway. I doubt that he'd tell her you're awful when you've got such a good relationship. 

To be honest he probably said "we'll see" because he's just as afraid as you are that the bond you guys have will collapse if something bad happens between you and his sister.

So yeah before you do anything you'll have to know you friend's opinion on this matter, it could be the difference between 9 years wasted and the greatest time of your life.

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