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Originally Posted by Five-ofan
i know the saying and thats partially why i made this thread. What has been overlooked by many largely because i didnt mention it, in knowing him since we were 7 ive known her since she was 4 too and she is also one of my closest friends.
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Call me cynical but this cannot end well. I am assuming that in the course of this 13-year relationship with these two friends, you guys hang out together. The way you all inter-relate would change dramatically. If even one of you is too immature for that, it could ruin both friendships.
For instance, I am assuming you met your best friend first and the little sister came along later or you became friends with the sister later in some way. He may feel your friendship is stronger than the bond with you and his sister. If you become serious with the her, he may feel jealous or threatened that he's not the one with the stronger bond. This is a problem with any girlfriend and best friend, but he also has the role of brother to play, and in this case, he could exploit that role when expressing his anger or in trying to change things back to the way they were.
If the relationship with the sister is simply sexual, he would be negligent in his role as the protector to tell you to stay away from her. Hearing your best friend say that you aren't good enough for his sister could be damaging to your friendship or he may simply lose respect for you because you treated his sister like a piece of meat.
You have to talk to him first, make sure he gives the okay, or it will never work. Obviously, you have to talk to the sister, too. It will take a tremendous amount of energy and effort on your part to maintain both relationships and navigate landmines. For instance, if she has a problem with her brother independant of you, you may feel compulsion to fix that problem by exploiting your friendship with her brother. In fact, the sister may even lobby you to do so, and at 17, telling her no could lead to her feeling you aren't a devoted boyfriend.
There's nothing wrong with dating a best friend's sister, but I think it may be too soon to consider it. All three of you would have to be extremely mature your your age for it to run smoothly.