long post, I don't give a shit.
My first love...well, initially she wasn't but became it. As I've said before I was homeschooled from 3rd to 9th grade before going to high school/college. Before the semester started all students attended an orientation event where we got to know each other, did various activities, etc. I got there a bit early, and as I was walking around someone yelled out "hey, you." I looked around and realized a tomboyish looking black chick had said it. From that point on she spent the next few weeks and months constantly following me around, talking to me, doing group projects with me, etc. For quite awhile I thought she was annoying because she literally wouldn't leave me alone but we became friends.
In hindsight we were quite different from our black peers. There weren't many black dudes in the HS portion of the school, and I was the only bookish, "nerdy" type. I was a backpack rap, Zulu Nation type taco who spent a lot of time in the library reading fantasy and sci fi books. She was rather tomboyish, played basketball with her brothers (one of whom will be in the NBA in a year or two), and just didn't fit in with the Mean Girls-esque clique of black girls at the school.
She used to troll me by telling everyone we were going to get married one day; then she'd constantly ask me wedding related questions ("what type of cake would you want at our wedding?"). At the time I thought she was mainly doing this to annoy me but I soon learned she was serious.

I went to her 16th birthday party and got to meet her family. After the party I noticed a lot of the people who came simply hugged her and left. Instead I decided to first thank her parents for letting me come; I shook her dad's hand, said thanks, and later shook my friend's hand which began the "handshake instead of hug" movement. Later I learned that her dad was quite impressed by me thanking him; I already knew her mom really liked me as well. But meh whatever, I was 16 and wasn't thinking about dating. That being said, my interest in her had began to move from simply being friends. I was attracted to her; she had begun dressing more feminine and it really highlighted how attractive she was/is.
Fast forward to her 17th birthday. It was around 11PM before I realized that I hadn't called her to say happy birthday. I felt shitty so I picked up the phone and called, not knowing what I was going to say. She answered, and I just decided to sing her happy birthday; it literally popped into my head the minute she answered. When I finished I apologized for calling so late. Then I heard multiple "awwwws" on her end of the phone. She had me on speaker phone and her mom, cousins, and aunt heard it.

Shortly thereafter she sent me an email saying she loved me and wanted to be my girlfriend; she also acknowledged that she recognized I wasn't really a relationship guy, but she wanted to try. I...turned her down. I said I was afraid that if we started dating it could ruin our friendship, and I thought of her as a good friend. She said cool and we moved on, but I could tell it hurt her. Around this time I would drive her to and from school nearly every day since we lived close to each other...and I noticed our car trips became quite quiet.
Not long after that she would up getting kicked out of school for violating campus behavior policy. Rumors whirled, people kept asking me if I knew what happened. Eventually I found out. I remember a lot of people around campus laughing about it, giving me weird looks, and just clowning her ("I never thought she'd be the type to do that lol"). I was so disappointed and depressed that I cut contact with her. In hindsight I was a dumbass. I still haven't apologized to her for this BTW. I should have been there to support her but didn't. I won't go into details but I basically slut shamed her - not to her face or in text (or to anyone else), but at the time I felt like I didn't want to associate with her anymore.
She was re-admitted a year later somehow and we slowly began to talk again. Eventually we were back to the way things were. She asked me again if I wanted to be her boyfriend, and again I said no. She asked one more time a few months later, same answer. I wanted to...by that point I began to realize we had a special bond, and there were so many weird coincidences that almost made me believe in fate. But I was scared and sure as hell wasn't ready to have a girlfriend.
We graduated and went to the same university, but didn't really see each other much. And that's where we really drifted apart. She got a boyfriend, got engaged, and eventually broke up with him. Meanwhile I brooded and wallowed, too afraid to just tell her how I felt. We went to dinner at one point, after her breakup, and I probably could have told her everything and won her right there...instead I didn't.
Now she has a kid and is once again in a long engagement with no marriage date. I haven't spoken to her in ages. I sent her a happy birthday message a few months ago but she never replied. In fact she hasn't been active on Facebook for awhile. I really think she must be going through a tough time with her fiance, based simply on the fact that she's been engaged for two years, hearing that she has gained some weight, and also hearing her fiance is kind of aloof; her mom has also made weird comments to me semi recently that makes me think she's not happy about the situation. I don't feel comfortable contacting her directly though, since I don't want to meddle. If not for the kid I'd probably be waiting in the wings, ready to finally tell her how I feel once she breaks up with her fiance. But now...it's over brehs.
In short guys...don't be a dumbass. If you feel strongly about someone, don't wait until it's too late. Tell her (or him). Even if she's your friend and you're afraid the relationship could be injured. Take that chance; if you're good friends I'm sure you'll be able to work it out.
