OK first some back-story. So I've known this girl since about 2nd grade, she has always been really nice to me and incredibly sweet etc, we weren't really "best friends" in school but we were definitely something if that makes any sense. Anyway in high school i asked her out, sort of, kind of (asked if she had a boyfriend and if she wanted one but she kind of avoided the subject) but I graduated high school thinking that i would never see her ever again.

But ever since then I've seen her almost a dozen times either walking down the street on completely different parts of town, in stores or on Facebook (big deal everyone is on Facebook) or on online dating sites.

OK so i should tell you she has a boyfriend (based on Facebook and dating sites) so should i even bother to pursue this at all or am i just too clouded by my own infatuation to think clearly? It should also be noted that she is without a doubt one of the hottest/coolest/most awesome girls I've ever known, so much in fact that each of my girlfriends since high school has more or less been based on her "template"

Do what you think is right, can't hurt to give it a go. But if she's happy in her current relationship just let it go. Even though she's your "type" it doesn't mean that there aren't others such as. You proved that by dating girls in high school similar no?

Was totally with you until I got to the part about how she has a boyfriend. In this case, I would recommend befriending her again and keep the relationship idea on the back burner. Catch up and all and see where she seems to be, and go from there.

why would you care if she has a relation? just care less and try if you're confident.

The universe doesn't want anything. To imagine so is pitifully self-centered. You are responsible for trying to shape your own life.

It's certainly possible. I became close with a girl that had a boyfriend, and she eventually left him for me. Plus, you'll have an immediate advantage, being a guy from her past.