What is your biggest regret?

I (M24) regret losing a bestfriend(F23). We were bestfriends since we were 13 - same school and same group of friends. We were chatting constantly about everything and were going out atleast once a week. Over those years, she had partners or h/u, while I wasn't as lucky and only had h/u. I always liked her. She was kind to me, genuine, smart, same interests, same sense of humor and extremely attractive - a perfect girl for me. Many people questioned our friendship and thought we weren't just friends, we both denied it because it was not true. I never told her that I liked her because I was scared of losing her as we were both too young and unexperienced, not too many relationships succeed at such young age. When I was 18, I was going out with a girl that played with me and viewed me as her puppy. She would pull me close and then push me, just to give me enough "crumbs" so she could keep me around. Over time, I had enough of that and ended things. Regarding that situation, my bestfriend told me "I don't understand why she would do that to you. If we weren't friends, I'd liked to be in relationship with you." I laughed it off because I didn't want to make it weird. After a month, my bestfriend told me that she has to tell me something. She admitted she was in love with me, but it was happened a long time ago. Again, I laughed it off because I met a girl who I started dating over time. also, because I was scared of losing her, we could say I wanted to keep her a last one. Kind of a jerk, eh? In meantine, she found a boyfriend that she really liked. I was happy for her, because we were both happy in our relationships. Eventually, we stopped talking and hanging out. Our communication went to wishing each other birthdays, new year, etc. From time to time, I would remember her and wished we were still bestfriends as we used to be. I missed her, but we both wanted to be fair to our partners. After 4 years of relationship, I broke up with my girlfriend because it was too toxic and we weren't happy. After few months of getting my shit together, my bestfriend invited me for a coffee. We didn't see each other for almost 2 years. I was excited to see her. We met, talked about basic things in our lives. She got a degree, found a dream job, moved in with her boyfriend. She got engaged. Flashbang hit me, everything was in slowmotion. I think she noticed that I was in shock because she knows me. I told her I am happy for her, honestly I really am. We both went our ways. I got home and cried for hours. Reality hit me. I had my chances. I lost her.

/r/AskReddit Thread