Alright, so there's this girl i ran into the other day that I went to high school with (I graduated 3 years ago). In high school, I had a HUGE crush on this girl. She has it all: looks, humor, personality, and we share many of the same interests (which is a bit of a rarity for me). And from what I've been told, she had a bit of a thing for me in school as well. However, she always had a bf and I had various gfs, so nothing ever sparked from the initial attraction. I am 100% single now, so when I saw her, a lot of the old feelings I had came back to me (and she's even more gorgeous now than she was in school, which I thought to be an impossibility!).

So anyway, I run into this girl at the grocery store, and she's with this guy who I assume to be her bf. I give her a hug (actually she initiated it, and it was a rather lengthy hug) and the normal "oh hey, I haven't seen you in forreever! how have you been?", but I keep it simple, because I assume the guy is her bf and I'm not the type to hit on a girl in front of her significant other (besides, I was with my parents). I find out later (after we've parted ways) that the guy she was with was her older brother, and that she is currently single. Naturally, I go on facebook and look her up (we were already friends), and I send her a message just stating that it was really cool to see her and I ask if she's still living in the area.

Now comes the question...what should I do next? She hasn't replied yet (which is understandable, as she recently had a family tragedy), but I think she will eventually. I really want to hang out with her sometime, mostly to catch up (but not limited to that), and I really don't want to screw it up. I've always kind of thought she was out of my league (I didn't have much confidence in myself when I was younger), but I'm not the same person I was in high school, and I don't want to let this opportunity just pass me by again. Help?

Anyone?

I could really use the help!

What you do is wait for her to reply.. Get her #, keep your interactions low investment and fun, and drive towards getting her out to spend time with you. It's easier to fuck things up between the point you are in now and when you take her out to hang out, then it is to fuck things up after you have made that first impression of being low maintenance, fun etc, have taken her out and been able to run game on her in person (if you ask me). So tread carefully and don't get too needy with the reply thing, she will smell your pussy a mile away and write you off before even giving you a chance to date her. Good luck!

Go for it! You've already sent her a msg, but I'd wait for her to reply before doing anything else and I'd personally hold back a little as people can be vulnerable and have a wide range of emotions when going through something like a family tragedy so they can not always be acting like themselves..

If you're mentioning anything from high school days, keep it to things that reflect really well of yourself or are humourous (not at your expense haha), there's no need to speak of anything that reflects your lack of confidence from back then..

good luck!