I've had a crush on this girl since Freshman year (6 years ago). We were pretty good friends then since we had a few of the same classes together, but she already had a boyfriend. I haven't talked to her much since then, just the occasional Facebook comment.

I only seen her one time in-person 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"

I was wondering if there was any safe way to approach her on an IM, since it's not likely we'll end up seeing each other in person soon? She's currently single, and from what it looks like on her Facebook, very interested in finding someone.

I can't edit my post since too much time has passed, but what I meant to say in that last paragraph was that I didn't know if just IMing her would be too random, since we've never talked on IM before. I don't know if that would make me seem too interested.

Just yesterday she posted a Facebook update that simply said "I need a man..." Is there something I could comment on that which may grab her attention?

Oh how much I hate facebook game, but then again, it works if done correctly.

Well, here goes:

You don't want to seem needy, demanding, in search.
You want to seem cocky, disinterested, but intriguing.

Facebook is a risk because its easy to not notice and take things the wrong way.

I do not know this girl or how close you ever were, I would respond with one of the following:

1. I'm playing the world's smallest violin for you. lol
2. You dont need a man, you need to get laid! Don't blush.

But if you want, you can open more directly with

1. I've got 8 already, but you can be my 9th if you want

All would be funny, and at least get a laugh.

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wix.com/djapplejacks/getanygirl
Soon to be www.getanygirl.co.nr

I want to Start A Project Hollywood, anywhere.
I currently live in Chico, CA and travel down to The BAY often.

I kind of like the "I've got 8 already" line, but I'm not 100% sure. I'll wait and see if anyone has any other opinions.

I'm not a fan of online gaming either, but it's really my only option at this point. We weren't really close, just hung out at lunch, chatted in class, and had a lot of common friends.

if you ever notice on facebook at the top right at "suggestions" sometimes fb suggest to reconnect with someone or say hello. you can maybe post something on her wall along the lines of "facebook suggested we should reconnect, hello!"

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-cbk

Good idea! How could I word it though to make her interested?