It's a TRAP: Dating the DSM* Manual Way! (Pt. 1)

My first true love, my first real heartbreak, and BOY was it a fucking SHIT SHOW. But if I learned from it, maybe you can too! Or maybe someone out there can avoid making the same huge mistakes that I made. Or maybe someone will just enjoy the schadenfreude that comes along with reading this.
First, a little background to get you in the mood...

SETTING THE SCENE
In high school, I was "chubby" (not really...) and pimply and awkward. And my best friend was the hottest girl in school (still one of the prettiest people I've ever known) AND the valedictorian. Nobody kissed me, nobody asked me on dates, and only ONCE was I ever asked to a dance. And hey, that boy dug the hell out of me, but he was even more shy and reserved than I was, so nothing happened. Hell, we hardly even danced. Like maybe one dance. We came together, and I mostly danced with my girlfriends. SO COOL. I was a mega-prude with NO good examples in my life of what a relationship should look like or feel like.

Then, toward the end of my senior year I started an OK Cupid account. This led to some very unchaste AIMing with a boy my age who lived about 2 hours north of me. Unchaste because he had the cajones to ask me things like, "what underwear are you wearing?" and I had the senorita cajones to answer. But I didn't want to, and it made me uncomfortable. I'd never been kissed! And you're asking about my UNDERWEAR?! Alas, it excited me, and it felt awesome to be LIKED. Especially to be liked in such a non-threatening environment as the internet. I could like him, I could talk sexy talk with him, AND I could continue to be a total innocent prude. It was baller.

At some point, we decided to take the relationship from the intertubes to real life, and boy did my tonsils regret it. He stuck his tongue as far down my throat as possible and, when I whimpered my protestations of "I'm not ready," he simply said "I am" and continued to palpate my uvula with his tongue. Really, obviously, the beginning of a beautiful relationship. No really, we dated for 2.5 years. Right?! That's how low my self-esteem was. But he was my age, and he liked me, and that was enough for me.

Our wretched affair lasted just long enough for him to see me through the death of my dad and dump me, like, a week later. Oh, and he didn't just dump me. He dumped me over the phone, and told me he liked to cross-dress. Uh? What? Who does that? I mean, that's fine and all, but that's a really fucking weird way to break up with someone. OH and then he told me to drive up to see him so we could have it out in person. That just meant me driving up at like 1am, him putting the moves on me, me sleeping with him, and me leaving in the morning feeling disgusting and dejected. Then I got the flu and missed out on our family's Christmas events. So that was pretty awesome.

TUNE IN FOR PART II: MEETING THE DEVIL

*=DSM stands for Diagnostic and Statistical Manual of Mental Disorders, criteria for classifying mental disorders.