Back near the dawn of time, I spent summer and christmas breaks working alongside a smart, beautiful, smart-ass girl. The banter was legendary. Never had I compatibility with someone that devastatingly intelligent, stunning, and, well, dirty. However, due to a high-school-ish lack of self-confidence and cluelessness, I assumed our linguistic sexual interplay was merely in the land of “let’s just be friends”ishness.

Eventually, our friendship progressed into letter-writing and getting together with groups of friends now and then. I think our flirtiness via snail mail and parties got to the point where I somehow indicated my real feelings, for she responded with a “I’d love to go out with you, but [her best friend] has a crush on you and I wouldn’t want to hurt her.” So after much soap opera garbage and letting down the friend easily, I got that first date. And it was spectacular; the specifics were better than I’d imagined (a story for another website?). This was an open-minded girl! But I stopped short of home plate that evening, I don’t know why: I’d never had sex, lack of self-confidence, first date, stupid, etc. And we went on for a couple of weeks, and here’s where the train falls off the track.

Rather than trying to reignite the passion and fun and fearlessness of that first night, I became a supreme fluffhead schmuck. A far-too-expensive necklace for Christmas. Teddy bears. Little gifts all the time “just because.” Discussions at her house, alone, without progressing to making out. Too much obsessive attention WAY too soon. Trying to show her the relationship wasn’t just about sex.

And then, well, it wasn’t. She let me down easy, but she never really explained why she broke it off, to my lifelong frustration. We wrote letters for a while, even with some of the flirty stuff thrown in, halfheartedly, but that was it.

And in twenty years, I’ve never met another woman with that same combination of smarts, beauty, humor, and pure sexuality. How’s that for schmuck?

Submitted by Snake, Age 35, Boston