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My best friend's sister


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Posted

I've been friends with this guy for 10 years and as I have got older I always thought his younger sister was cute, but she was young and never thought anything of her. Recently though I'v noticed her more and I want to ask out some time but I dont know how to approach this b/c this will be out of the blue for her and she probally just always thought of me as her brothers friend and thats all. Shes 19 and I'm 22. I know my friend would be fine with this b/c he once asked me to ask his sister out after i broke up with my previous gf. I guess I want to give her a hint that I'm interested in her before I do anything. Any advice on how to go about this would be great.

Posted

Well, getting involved with your friend's sister could get messy. What if you guys break up? Or fight? You won't be able to really talk to your friend about the girl your dating because it's his sister and that would be very ackward.

 

On the other hand, it could work out beautifully (i.e. Chandler and Monica on Friends). That's not real life though. I honestly think it would not be the best idea. Your friend may be fine with it in theory, but the reality of the situation is a totally different story. If you like to talk to your friend about who your dating, you probably wouldnt be able to do that. Also, if you break up it might make your friendship more complicated, especially if it gets messy. There are a trillion girls out there, pick one that doesn't have any relation to any of your buddies.

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Posted

I understand what your saying but I know are friendship could handle this. I know theres plenty of other girls, but I'm curious how this could work out. If things get complicated i will back off, but i have to know how this could work out.

Posted

The brother encouraged you to ask his sister out. For all you know this could have been the younger sisters interest in you manifesting itselfs.

As for the rest of the issue, tread lightly.

Posted

Don't do it.

 

If your around when they are both fighting, who's side do you take ?

 

thats just one of the many annoying things that are involved with dating a friends sister

Posted

I actually dated my friend's sister over last summer. She had liked me for awhile, and I found her attractive, so I went for it.

 

The relationship certainly wasn't perfect (she was WAY too intense and possessive) and I was the person to end it, but it didn't change my relationship with her brother. I treated her respectfully and maturely, and broke up with her before we got too serious.

 

Frankly, if you treat her well, and are respectful and honest with your best friend, I think you'll be alright.

Posted

I dated my brother's best friend years ago. It was fine.

 

As long as the two of you are mature enough if there's a breakup, there won't be issues. If one or both of you becomes territorial with the brother, such as demanding he be in your camp, this is when issues happen.

Posted

This is a definition of a recipe for desaster but again it could totally work out. That is how life is, so I do suggest take a chance but you have to be really careful with how that relationship progresses. If there is brake up to occur you guys need to do it like grown ups again because you will ruin your relationship with your best freind other wise.

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