I met Karen at a party at an indie clothing company on the South Side. I’m not sure how or why I got invited. The thought of underage kids drinking at your place of business seems like a risky proposal now, but it didn’t strike me as unusual at the time. There was a keg downstairs near the bathtub where they bleached and dyed the clothes.

I went to the party with Kristen, the first girl I ever dated from my own high school. Kristen was an diehard Smiths fan, and I’d started noticing her sometime during our sophomore year. She always sported coiffed hair, horn-rimmed glasses, cardigans, and trench coats. Naturally, I was smitten, but she remained out of reach until our junior year when our mutual friend L.J. introduced us.

By then, however, in a highly unusual teenage transformation, Kristen had become more interested in Mötley Crüe than Morrissey; an inverted version of my own trajectory. Her faux pompadour had grown bigger and longer and become more blonde. At the merest taste of alcohol she acted shit-faced drunk. Somehow, even at sixteen, I found this quality unattractive. If we had had a place to go it might have been different. At that age, though, when we were relying on our parents for rides, I got tired of being known as the guy with the drunk girl. I quickly discovered that making out with her severely limited her chances of doing something stupid, so that became my strategy for much of the night.

At some point during the party, when I was lip locked with Kristen, I saw Karen sitting on the rickety wooden stairs, crying in the way that only a melodramatic high school girl can cry. She had long hair with no discernable style, in defiance of the prevailing fashions of the mid- to late-eighties. Her lipstick was a little too red and was even more exaggerated when contrasted with her pale skin. Her clothes, however, were the requisite black and flowing style of the day.

Somehow I managed to strike up a conversation – of the consoling type, no less – with this girl who wasn’t my date. She was upset about her on-again off-again boyfriend, who at that moment was off-again. Maybe he’d met a new girl. I don’t remember. Karen then was just my type: vulnerable and sensitive, unlike drunk and brash Kristen. If I could help her in some small way by making her ex a little jealous, then so much the better. I still amaze myself when I think that I used to do things like this.

Probably the longest amount of time that I spent with Karen was at her house after school one day. We hung out in her room in her parents’ Tudor house, which was much fancier than my parents’ new construction suburban box. Though her house was smaller than most of those nearby, it was nevertheless in an exclusive and desirable neighborhood. She told me stories about her abusive father and her meatheaded jock of a brother. She was also a misfit at school, constantly being harassed by the cheerleaders for her nonconformist style. All of this only endeared her to me more.

We talked about music (she was particularly fond of “that New Order song from Pretty in Pink when Andie makes her prom dress”), our mutual acquaintances, our shared hatred of our public schools. We were on the same page. Then she put on a Prince tape. Parade, to be specific. Karen was obsessed with Prince, all the way down to his bell bottoms. I had never listened to him, except for seeing “Purple Rain” and “When Doves Cry” too many times on MTV. I didn’t really think much of him one way or the other. He was better than Madonna, but that was about as far as my analysis of his talents went. But this record was different. This was lush, kaleidoscopic, dreamy pop music. It was pretty, sexy, and exotic. It would not have been my first choice, but I have to give Karen all the credit she’s due. It was great music to make out to.

Then, as all great things must end, her father came home. Karen, as frightened as I’ve ever seen anyone, rushed me out the back door. Before I left I managed to make a phone call to my notoriously unreliable older brother, who took his sweet time coming to get me. I stood a few blocks away from her house, waiting for what seemed like an eternity. During that time, of course, it started to rain. Hard. I was soaked when my brother finally showed up.

I saw Karen a few more times after that, but by then I was meeting other girls as well. I was still flush with the idea that girls didn’t find me repulsive – a fairly recent discovery at that time – and my friends didn’t like Karen. They thought she was flaky (granted, she did put suntan lotion in her hair once, thinking it was gel). They never knew the sweet, charming person that I knew.

When I met a girl named Laura and was tempted by the thought of getting to know someone new, I made what I realize now was a mistake. I listened to my friends. I broke up with Karen in that uniquely high school way: I avoided her. She never confronted me about it. Later I heard through the grapevine that she dated a jock after we stopped seeing each other (à la Penny Hardwick in High Fidelity). That made me feel even worse.

I haven’t seen Karen once in the twenty years since that time, and all my attempts to find her have been fruitless. Parade still makes me sad when I hear it.