A relationship with a best friend's sibling?

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This right here is your warning and the reason why I don't think you should do this. All of your posts are about his shock, surprise and disbelief. It sounds like he isn't really ok with the idea but may eventually make his unsteady peace with it if you and her are happy together. However, if anything goes wrong, you will be the bad guy in his eyes and you will lose his friendship. He has already warned you of this. Yes, technically he did say "if you do wrong by her". But if something goes wrong and it isn't your fault, he will still perceive it as you do wrong by her because she is his little sister and he will put her before you.

This is a bad idea. It is making uyour friend uncomfortable and he will be unforgivingly angry with you when you and her break up, as you eventually will unless you marry her.

The parallel saying is "sisters before misters". And she is his sister. Little boys put the well-being of their friends above the well-being of their sisters. That reverses sharply, very sharply, in adulthood.

Pursuing this relationship would be a bad idea.

Not necessarily. If her family already thinks highly of him, then not much can change that. The comment about losing his head seemed like more of a warning anyways. Just because you're friends with someone, doesn't mean they're good and honest with everyone they date. That's probably what the warning was about.

Besides, if he really wants to date her, I don't think he could ever be in a better position for it. He's already on good terms with the dad and brother. She likes him enough to do some pursuing on her own. If things did go bad, things might get a little strained, but unless he did something horrible, I don't think any permanent damage would result. People aren't exactly quick to change their opinions of someone.

(Usually that's a bad thing, but in this case, it'll only work in his favor.)

Actually, you mean her mom and stepdad. She rarely sees her dad and the only time I've met their dad was when my friend and I graduated from middle school six years ago. And about my best friend-I don't think we've seriously discussed it, and knowing him, I think the only thing he would be uncomfortable about is the awkwardness of the relationship itself-and I think over time he would not just accept it, but embrace it. He wasn't at first nuts about Facebook, and guess who was his first friend on Facebook?

UPDATE: As of 11pm last night, and confirmed today, the two of us are dating.

Congratulations.

As long as neither of you decides to be an ass, I'm confident that things will work between you and her. You've got a better situation for dating than most people could ever dream of. Just make sure you play nice.

Thanks! First, neither of us are asses, second, her mom has been really understanding, and third, the fact that this for a long while is going to be a fairly long distance relationship is only going to make us have to work harder to make it successful. To be honest, I couldn't ask for better.

In fact, both of us have some form of disability (she has severe hearing issues that require her to wear hearing aids, likewise for her brother), and I have AS.