My friends went to a Con when I was in sophmore year of highschool. (so like, what, fifteen?) They came back with all these stories about "con" and how much fun it was and yadda yadda yadda.
I was not an anime person, still not terribly, and probably never will be much (I like a select few animes, but most don't appeal to me) so I shrugged it off. They started making me watch anime to help me understand, which it didn't...(they started me out on Love Hina, which, when you've never seen anime before, and are alone in a dark room after everyone else has fallen asleep, is buku creepy -_- )
But con never the less sounded amazing, especially since I am a webcomic, videogame, RvB, etc etc nerd.
So we went to the local Sakura-con the next year. I ironically got a sewing machine for my birthday and planned cosplays.
I was a little overzealous. Being a theater kid and a crafty person, I get overambitious with costumes reaaaallly easily and not understanding cosplay, as I had never seen it, I did really amazing halloween costumes. Which make only half-a**ed cosplays. I did a Soot Sprite for Spirited away which nobody understood and ended up looking saggy and weird. Skull Kid from Legend of Zelda, which had an amazing mask...that was too heavy to stay on my face and had to be carried around, and the costume was otherwise crappy and suspiciously racist looking.
The only good cosplay I did was an original character (and ironically the only one I was complimented on several times) that had a straight jacket I made myself and was self locking (a feature some guy wanted to know more about, which made me more than a little suspicious) and a toaster strapped to my back on a cord bandolier. Oddly enough, as crappy as our first costumes were. I really loved it. More than the Anime and the merchendise, which is what some people seem to be only interested it, it was the environment and the costuming that really brings me back to con. I'll probably be finding ways to cosplay even after I'm old and it's creepy.