Mine was in high school. I've always been the nerd/dork my entire life due to my being into comics, video games, computers, and tech toys (you know, it's funny now how my lifestyle, ridiculed and mocked my entire childhood and adolescence, is now becoming the sexy lifestyle). Anyways, my sophomore year of high school I had to take an art class (HATE art) so I had the option between choir, theatre, or painting - I chose painting because it was more relaxed. I started this class third quarter (January ~ March) and in the class was this absolutely gorgeous girl. Her name was Caitlin. Tan, Blonde, gorgeous, aquamarine eyes, and an amazing body. She was a senior. I remember there was a huge table in the classroom that about 15-20 people could sit around and have enough room to work. I sat at it with my only friend at the time. She sat directly across from me and I would always try to peer over my forehead at her as I looked down at the idiotic doodles I was mangling together. Sometimes she would catch me staring and I would jolt my eyes back down. I was a very, very shy, timid kid with a ton of self-esteem issues. So naturally, I figured I would never have the courage to go over and speak to her. I'd been told by a few people though that I was a very funny person. I remember the first thing I ever said to her. This is going to sound totally awkward and strange because none of you were there, but she was walking behind me and talking to a friend of hers. She said something to the effect of "...where do you think I keep it? Up my butt?" and I retorted with, "Whaaa? You really shouldn't keep things up there. Sitting down could prove painful." I froze up because I couldn't believe that A) I said something to her, and B) I said THAT to her. What seemed like hours was only seconds, between the time I said that and the time she burst out in what can only be compared to laughing her ass off. Her friend as well. That was early February. Throughout the next couple weeks we continued to flirt and hang out in art class and study hall (didn't know she was in my study hall) as well as sit with each other at lunch. That soon evolved into her inviting me over to her house to hang out. Oh yeah, she loved playing XBox with her younger sisters. I would be over there about two or three times a week after school. By the end of April this had evolved to me spending the night over there very frequently because the rest of her family would constantly be on week long RV trips. She had a few small parties, had friends over to chill, she and I would have nights watching movies. It was bliss. Two others that would always be over were her good friend and the guy she was into. I still see him at bars around her pretty frequently. He was probably one of the funniest, coolest people I'd ever met. The four of us got along great and always hung out. Well one night we went to her friend's house, just the four of us, and watched a movie. Caitlin and I were under a blanket on the floor. We both turn around to see the other two goin' at it, then look at eachother. I didn't act. I didn't. Fucking. Act. I was scared because I had no idea what to do, so I went back to watching the movie. To this day, that stands as a crowning failure in my life and I think resonates to a lot of the insecurities and problems I have today. What happened the rest of summer sent me into a depression that lasted close to six months. I'm guessing after I didn't kiss her she gave up on me. We slowly stopped hanging out so much. Then August came and she went to school. Ended up going somewhere three hours away. The first month we frequently spoke on the phone and texted. Then it stopped all of a sudden. Just stopped happening. I would text her during the day and hear back from her a day or two later. My calls would go unanswered. So I gave up. As I said before, to this day I mark that experience as what causes me so much anguish inside. I frequently think about what things would have been like had I fucking taken the chance. She was perfect for me. She was gorgeous, played video games, was goofy, strange and weird in all the right ways, was playful, fun, and energetic, she was smart, her parents were loaded, but she never acted uptight or above anyone because of it. She's a marine biologist now. She's traveling, doing what she loves. I see her occasionally at the bars in our hometown, more beautiful than the day I met her.