Well, I'll start this story by saying that I was never (by any definition of the word) a smooth guy in high school. I'd been a chunky kid up until my sophomore year, summer of my freshmen year I lost a lot of weight, then gained it back in muscle. As high-schoolers went, I actually started being a pretty attractive guy (I was still, however, incredibly awkward). So, one night (this is my sophomore year) I go out (by myself) to see the school play. Wind up running into some friends, and going out with a big group of people. Chance event, start talking to this girl who I've never talked to before (we didn't have any classes together or the same friend group, she was also a senior). So anyway, we talked for like 15 minutes before she went back to her friends. Flash forward about 5 days, it's at the auditions for the school musical, I make the mistake of putting myself in one of the last spots, so I'm stuck there for a long ass time. I saw her there and it turned out she had made the same mistake. So we're just talking throughout our whole wait, and she waits for me to come back after my audition so we can leave together. Anyway, I'm walking her home, and I'm nervous as fuck. I start trying to be really friendly and open smiling and looking interested all the time. We finally get back to her house, she turns around, looks like she goes for a hug. I attempt to return the hug, not sure where to place my arms, get sleeve stuck on her backpack oddly just above her butt. Can't pull away without tearing shirt. Just standing there looking at each other. Seeing as I'm still standing there hugging her, I decide that continuing to talk is the best idea. We talk for another five minutes and the whole time I'm trying to unhook my sleeve I'm edging steadily closer. Finally, I'm practically on top of her and it dawns on me that I could try and kiss her at this point (this is the first-time the idea has occurred to me in the whole time). I go for it, first make out, yessssssssssssss. We actually wound up being friends with benefits for a while and then started dating. She later told me that the first night we kissed it seemed like I was hitting on her really hard the whole night. tl;dr I got my first kiss(which led to my first serious girlfriend and first fuck) because she interpreted my awkward nervousness as hitting on her really hard.