To ask, or not to ask?

I am normally pretty good at things like this and don't require help very often. But even the best need help sometimes and this is where you all come in.

So I hope you are all ready for a little story that takes us back to 2003. Take a moment to think of what you were doing 13 years ago...

Okay, so I met this girl back in 2003, elementary school, 3rd grade. We became pretty close friends. she gave me a "nickname" that has stuck since then. I'll say now that I did have a crush on her. <-- remember this. She moved away and it made me pretty sad. We kept in touch though for about a year and for some reason we lost communication.

Jan. 2010

She shows up at my high school. It was one of the happiest days I've had in a while. She had just moved back into town and she told me she would be attending school here. End of that chapter.

Why not tell her how I felt back then, or try and see if I can make things work between us? I would have, but I had a girlfriend at the time... And we didn't talk much.

June. 2013

I graduate high school, girlfriend and I break up. End.

Nov. 2014

Our friendship finally starts to rekindle after I messaged her. We go out for coffee have a good time. Goes on till this date. Sort of.

Feb. 2015

I ask her be my valentine. yes.

July 2015

She moves away again:/ for school.

Jan. 2016

We Skype every now and then. 1/26 be my valentine? yes. (more in update box below. Stupid character limit)