My very first relationship with a girl began long before either of us knew what a relationship was. Growing up I was inseparable with a girl who lived on my street. We were too young to understand romance, we were just best friends. We went to the same school, and we were always together. As we got older it became sort of understood that were a couple, as much as gradeschool kids ever are. It was like an elephant in the room though, we never openly acknowledged it to ourselves or anyone else, I remember being teased goodnaturedly about her by friends and sheepishly denying my true feelings. Eventually I brought up the idea of being boyfriend and girlfriend when we were about 11 years old, and she said she wasn't ready or wasn't sure or something. We started drifting apart and eventually I found out she had a crush on my friend. For some reason that revelation utterly devastated me.
That was my first experience with love and heartbreak.
My first sexual relationship ended a bit more amicably, for me. My first real girlfriend and I dated throughout my sophomore, junior, and half of my senior year in highschool. I think we were in love for a while, but at some point near the end my interest began to diminish. I had a female friend at that point who I was spending more time with than her and we were developing feelings for one another. My girlfriend realized this and tried at first to hold on to me tighter. That didn't work and she decided we shouldn't date anymore, just 'see each other', whatever the hell that meant. So we drifted apart further until one day I heard from a friend that she had kissed some guy at a party. She vehemently denied it, but I was furious and told her we were done and flipped out and made her cry. To this day I'm not sure if she really did kiss that guy, but I feel bad about the way I reacted because at that point I didn't really care anymore anyway.
My worst breakup of all was about two years ago. I still have trouble thinking about it. She was the only girl I ever knew for sure I was in love with. We dated for a little over a year, and it was bliss. Then one night I got drunk and cheated on her with some pig who had been after me for months. I didn't think anyone would find out, but the very next day it was frontpage news. She broke up with me through a mutual friend and wouldn't answer my calls or return my messages for about a month. Then she just came back to me. Everything was different from then until the end though. We made it work for two or three months and then she left me for good. Looking back I think she came back because she couldn't quit me cold turkey and was just trying to ween herself off of me without actually intending to stay with me much longer. I still loved her but she was learning how to unlove me right infront of my eyes. The whole thing was just a big mess, and it haunts me.
So there you go. My top three most painful breakups.