I don't think a lot of you (yeah even those of you who cite your entire life story) come close to the level of fail I've achieved...
It started with a girl I liked in high school. Now a little background info: At that time me and a bunch of friends were playing a browser based space simulation (Ogame, if you heard about it), and I was the "leader" of an alliance within that game that included me, my friends, and some other guys that we never met but that we let join.
Entering high school, I kept the fact that I played that game (or any game for that matter) mostly to myself. Yet overtime, my physics class (which included HER) came to find out about it and to my surprise, a good portion of them (8/12 people) came to play with me and join my alliance... including her. she even asked me for "special classes" for the game. Needless to say I was in pure joy at that time.
Now comes the fail. Not all being from the same region, we would all chat semi-regularly with the members whom we didn't know in person, and just as I was working up my courage to go talk to her, I found out that her and one of those members were actually "in a relationship", despite never having actually met face to face before and always talking through the phone (a fair distance separated them), even having said the words "I love you" (I got confirmation of this the next day after I learned about it.) I quit playing less then a month after that and face-palmed too many times to count.
Long story short: I basically shot myself in the foot by being creating an alliance in an ONLINE BROWSER-BASED GAME! Beat THAT Level of fail!
although in retrospect, and considering the fact that they both are still together and have been for the past 3.5 years. I guess on some level they were meant to be, thus I have almost no regret from that entire story even though I sometimes think to myself that things might have been different if I never created that alliance... or even played that game. (Although those assholes never thanked me for playing involuntary cupid... despite her new-found "boyfriend" being aware of the fact that I had feelings for her)
I'll be waiting for a challenger to my story. Come if you dare!