The one that got away/had a shot but you missed it
 

I know theres a similar thread to this one, but have you ever went back for the one that got away, as in you had a chance to date them, never did and intentionally worked to get back into contact with them and dated them? if so, did it work out?

im asking this because I always hear about the one that got away, has anyone had an experience where they did get away and them you got yourself a second chance?

Also, this ties into what I heard at dinner a few nights ago from a friend of mine, there was this girl that he liked in high school, I don't think she liked him as anything more than a friend. They lost contact when they went off to school, she's in SoCal right now. He knows that she has a social networking account, but never added her, maybe it was because of his feelings for her, I have no clue why. Anyhow they haven't seen each other in about 4-5 years now. The thing about this guy is that he was good friends with her, but never really knew how to convey his feelings to her. Out of the blue he got a chance to talk to her sister and her sister mentioned that it was her grad/birthday this week. So He logs onto his account and sends her a message saying congrats and happy birthday, she sent him a message back saying thanks and that she misses him alot and that she was actually surprised to hear to from him. She's single and now he's looking for his shot.

What are your thoughts on what he did, do you think that he should've done that or should he have just left it alone and let her live her life without him in it. I personally thought it was a nice gesture, but for me I probably would have left it alone.

you'r....i mean he is looking too much into it. It's nothing more than a friendly gesture for her to say she misses him. Keep going forward and don't look back, otherwise u'll kill urself with "what-ifs"