When I was actually four. It was a girl named Emily who I went to pre-school with. She's actually my first kiss, too. However, it wasn't serious, of course. I mean, come on, we weren't even in Kindergarten yet. So I never count her as "official."
Then in second grade, this new girl moved down from Alaska, named Gillian, and I hated her. Seriously. However, a few months later, she was lonely, came up to me asked if she could hang out. I almost said no, but I'm glad I didn't. About a month later during a school day she asked me to be her boyfriend, I said yes, but we broke up two hours later. Ironically, this would be my best friend!

We still are great friends seven years later. I don't count her as my "official" first, either.
Then in sixth grade, another girl I was good friends with, Paisley, asked me out, and I said yes. We lasted quite awhile. She's my first "official" girlfriend. I asked her out to our first ever school dance. We never kissed, but we lasted a good five months. We never officially broke up, it's just that she moved away and I actually haven't talked to her face-to-face since August of 2007. We texted back and forth a couple times, though. The last text talk we had was back in January of this year. I remember because we got to talking about how her uncle Christian Cantwell, did in the Olympics and how everyone at my school couldn't stop talking about it since he grew up in that town.
My last girlfriend was not too long ago. She's the first I actually asked out, and her name was Megan. I asked her out in March of this year, took her to the crappy Spring Fling and the awesome 8th Grade Banquet and Dance. We actually had our first kiss at the Banquet. I count this as my first official kiss. I was so nervous, too! We broke up on Father's Day. She broke up with me through text, but then called right after to see how I was. We're still okay friends, but there's always going to be this weird awkwardness between us.