Up until my second year in college I had zero experience with women. There was this adorable girl in my anime club and somehow I ended up going from hanging out in a group with her, to hanging out occasionally with her just the 2 of us. We did normal friend zone stuff, get lunch, hang out watching anime, going to the theater, playing tennis, etc. Pretty much no physical contact or affection, not even a kiss.
Then after about a year of hanging out, things seemed to be heading towards a more serious direction. We'd get dinner together, sometimes at upscale restaurants, we'd watch anime at her place and it'd sometimes run all night into the morning, and I'd sometimes sleep on her couch, we'd go for long bike rides, even went to an open air observatory and watched the starts together for hours. I even met her parents. Still little to no physical contact, maybe leaning on each other on the couch, still no kiss.
I finally work up the nerve to ask her out on a proper date. (Although I was still too chicken shit to call it a date.) Nice Italian restaurant and then going to a live violin recital. I had worked it all out all romantic like, the restaurant had a real cozy vibe, soft lighting, fancy decor. The violin recital was held in a church, took place after dark, there were glass walls so you could see the stars, and everything was candle lit, or had that feeling.
Well before the date even started, we head to my place to kill some time. I don't remember too much of what we did but I do remember giving her a playful spank with my violin bow and she didn't seem upset about it. She was wearing a dark colored sun dress, that kind of looked like camouflage, and I had a fake army helmet that kind of matched and she put it on acting all dorky.
It was all so perfect. The moment seemed right, I went in for a kiss, my first ever kiss... and I completely missed her lips. I think I kissed her chin or something, I was completely embarrassed. I threw myself back onto my bed, wallowing in shame for what felt like days, but was probably seconds. I jumped back up, gave her a quick awkward kiss on the lips, said, there I did it, then flopped back on my bed, feeling like a total looser.
We still went to dinner, still went to the recital, even went for ice cream afterwards, but the whole night I was just embarrassed and mostly quiet. A few months later, I finally work up the courage to tell her that I like her. She flat out rejected me, saying she didn't like me that way. We still hung out but I was just crushed the whole time. Maybe I thought there was still a chance, I mean, I thought for sure she had been sending me signals or leading me on or something.
I ended up dropping out of school and joining the Army. Not because of her but for unrelated family problems. In basic training when we got our cellphones back for a couple hours as a reward for something, I couldn't get my parents on the line and she was the next person I called. Later on after basic, I send her a little teddy bear with an Army uniform on it and she, and her mom for some reason, told me she loved it.
By the time I made it back from the Army, she had already moved to another state and was planning on moving out of the country. I drove across country to see her one last time before she left. That was about 10 years ago and I still haven't gotten over her. Just typing this out filled my chest with a crushing loneliness. I'm sure she's already moved on after all these years, or that I never really had a chance with her and it was all in my head, but I don't know if I'll ever be fully over her.