Crush on a girl, how do I approach her?

More of something that I have been dealing with inside my head for months now. I would like input if you are able to.

I[18 M] don't know where to start explaining, so I guess I'll start at the beginning.

I knew her [17 F] before we were friends through her two older brothers who were in an elective class I was in. Had some decent conversations (decent for someone who was awkward talking with girls at the time [14]) with her from time to time. She seemed very interested in getting to know me; I don't know if that was just her being friendly to me or what.

I really did not get to know her well until I was in the 11th grade when she just started high school, when she picked the aforementioned elective. I guess by luck we were in the same class. We started becoming good friends; talked to each other from day to day. She did, like many other people in the class, look up to me as a role-model. (I guess this is a good time, if any to mention, that the class was NJROTC ... blah blah details... You can google the details.) She stayed in the program for a year, but we stayed friends afterwards until the start of the following school year.

Now on to my senior year. We did not talk as often as we used to as she was two grades below me and classes did not line up. Anyway, prom (and military ball for JROTC) season was coming up, and since it being my senior year is supposed to be the year where you show off and all that good stuff. A few of my friends asked who I would take. That's when I mentioned I had a crush on the girl. Some were surprised and others not.

After mentioning that I had a crush there were a couple of times one of my friends (looking back I guess he was my wingman) tried to hook me up with her. We talked and caught up with some things. But...

Spoilers I never did ask her out. The reason: there were various personal reasons I had and it was not her. *Couple months before I got together with another girl and it did not end well on multiple levels with her and friends. I was still recovering from that. (One of things I regret most in my life, but different story entirely) *After that incident my mom said no dating in high school. *I had to rebuild trust for a good recommendation for a scholarship in order to go to college. *I also had to maintain grades for college acceptance. *And then I was wrestling with a thought: what if I did go out with her, but it did not work out. What would happen with the friendship I had with her family?

Prom and military ball passed, but she started giving me mixed signals. We started talking a little bit more often. Then the end of the year came, graduation, parties, and all that stuff, and moved away shortly afterwards. For the next couple of weeks I felt homesick and regretted not asking her out. I have not talked her since then, guess I am too ashamed (hard, empty feeling to describe) to talked to her. Weird thing is I talk to her brothers from time to time through facebook.

6 months later, I am going to visit home with family and friends over the holidays, and this thought of if I should ask her out or not has been in my head for months. I just need some advice. Thank you kind reader and Happy Holidays!

tl;dr: I've [18 M] known this girl for 4 years now. Didn't become friends until 2 years ago. Really did not talk to her last year because so much was going on in my life. She gave me mixed signals before I moved. Have been in contact, because I felt embarrassed and/or regret (hard feeling to describe) just leaving her. Going to visit home for holidays. Should I start over, ask her out, or give up?

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