How do I tell my best friends sister I'm interested?

[nakota2k]

-Been best friends with this guy since we were todlers. His sister is two years younger than me. (22)
-Their parents are like my second parents.
-I see her a few times a year and we always get along and laugh.
-I feel like me and her have a more brother sister type relationship since we've known each other so long.
-She's a really shy person and wife type material. Wouldn't be surprised if she was still a virgin.
-Haven't told best friend but sure he would be fine with it.

I can't just ask her out because if it some how fails, every time I'm with there family it will be awkward as hell. What can I say that will beat around the bush and kind of test the waters to see if she is interested without coming straight out and saying lets date.

[LifeInflux]

Mention to her in passing that you used to have a crush on her or something similar. That way if she responds saying that she felt the same way, you have a starting point... if she says nothing and you can gauge her reaction as being negative or uninterested, reassure her that the feelings have long passed and that you didn't think she was interested anyways, but you're over it now.

[nakota2k]

Mention to her in passing that you used to have a crush on her or something similar. That way if she responds saying that she felt the same way, you have a starting point... if she says nothing and you can gauge her reaction as being negative or uninterested, reassure her that the feelings have long passed and that you didn't think she was interested anyways, but you're over it now.

Good advice thanks. I think I'm going to send a msg via facebook to feel her out, no pun intended. We just hung out today both our families for 4th of July. Maybe I can say something like "It was great hanging out yesterday. You know I used to have a crush on you, its too bad you live out of state." (she goes to college out of state for another semester). Something along those lines, its still pretty straight forward I dunno

[UnderTheMoon]

Flux is right. Definitely the best way to go about it. Good luck in trying to get the girl! Hope all goes well!

[searock]

Straightforward is good. Go ahead with that message, keep us updated.