What has been the biggest regret of your life to this day?

I didn't get to know my first crush more. I was 12 at this time and I was struggling with my attraction to girls. I didn't even know it was a crush at that time, but it's still there. Let's call her Raven, because that was the nickname I gave her when I didn't know her name.

Raven moved away and I did too, but even though we're still in contact to this day and we are on good terms despite our difference in general mindset, I have never been truly able to forget her. I've had other crushes, I've fallen in love, but she's still somewhere in my heart. It's been 7 years and I still wish I could go back to that winter of 7th grade when I had just arrived in the middle of the school year.

Raven and her friend had come to warn me about a girl who had talked to me in a very mocking way. They said this girl was a bully, and that I should stay away from her. I could never thank them more. I already didn't feel that girl right. But then, I felt so curious about Raven for some reason... and I found her so beautiful too. This nickname I gave her was because of her hair and skin. Black hair, dark brown skin (she's Sri Lankan). Reminded me of a raven's feathers. I didn't know her name. I didn't until the next year when I found her on Facebook. I watched her from across the school yard, but we only talked a couple of times. I was sad not to see her anymore when I left school and turns out, she left that school too.

Later on I try to find her, but without a name, it was hard... until I stumbled across her profile by looking through a mutual friend's list, and I learnt her real name. I was so happy. I added her as a friend and she accepted, and we talked for a while, but I definitely felt we weren't on the same wavelength. She's not really the brightest bulb in the room and I got frustrated at times, but I was happy to finally be able to talk to her.

But God do I wish I had done that in school. I could've got to know her even better, and maybe...? Maybe I could have kissed her? At this age, girls tend to experiment, and I just wish my shy ass would have got the nerve to approach her.

/r/AskReddit Thread