I've been waiting to get with this girl since my freshman year of high school in '04. I just wasn't very confident back then, but I kind of have slight approach anxiety, mostly because I have no idea what to say.

Her and I were friends our freshman year. Had a bunch of classes together, share a similar circle of friends, but we weren't close. Just one of those friends you hang out with at school, and that's about it.

I seen her at Wendy's 2 years ago, and when I got home later that night she had sent me a message saying "Hey, I think I seen you today at Wendy's, but I wasn't 100% sure it was you", I replied with something like "Yeah! I would've come and said hi, but I seen you were with your boyfriend", and she was like "aww, you should've! lol" -- Someone told me that if there was nothing, she wouldn't have even bothered to send that.

She's very open about finding someone, as she frequently posts status updates saying "I need a man," and stuff that puts her out there. Those usually get a few comments by guys saying "I'm a man," and guys being too cocky.

I need an opener that will charm her from the get-go. Nothing sexual though, as she was diagnosed with cells that could one day lead to cervical cancer, so I have no idea how she would react to it.

Any help on this would be greatly appreciated!

Ask her if she'd like to go to vegas and get married by an elvis impersonator with the hotel staff as the audience.

I've used it, girls laugh. Plus makes them think of you in that way.

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Don't stress about the opener on this one. She's already shown interest, so you just need something confident and non-creepy. I'd just use something plain like, "hey, why aren't you on my fiends list yet?". Then send it in a friend request (sorry for the myspace example, but I only use facebook for family shit and sarge on myspace).

I did the same exact opener on myspace for a chick I knew back in high school, which was about 10yrs ago, and it worked great.

I've had her on my Facebook friend's list for about 6 months now.

Would it be safe to IM her with a simple "hey, what's up?" or would that be too random since we've never talked on Facebook before?

I'm probably over-thinking all of this. lol

Yes, I'd IM her. If she's into you she'll be pleasantly surprised.