An Anti-Valentine to McSweeney's Men

It all started in 1995, when I couldn't get into a Chumbawumba concert on Houston Street in lower Manhattan. I was 19 and had never been turned away anywhere before. The bouncer was nice enough, but it didn't matter. Inside, I could see my friends – my sort-of friends – a motley crew of quirkily attractive, soft-around-the-middle 23-year-old men with the exact same beat-up satchel, the exact same Mead notebook, and the exact same smirk.

They wrote for or avidly read McSweeney's or its precursor, Might, and were members of the Dave Eggers-led cultural movement, then at its apex of hipness. I could see them through the window but couldn't get their attention. I was too embarrassed to try to charm my way in, so I just went home, holed up in my room and read George Steiner's Proofs and Three Parables, which I'd been lent by one of those guys on the other side of the glass. But the book was like him: too smart for me.

That was one of the worst summers of my life. Fantastically depressed, I was staying with my parents, fact-checking and baby-sitting and waiting for the fall, when I would start college. I had been semi-in-love with a dozen people by then, but none of those crushes had screwed me up. Those had been fun. But this crush on the guy inside the club I couldn't get into – this one was torture.

The clever, conceited men of McSweeney's – for they were almost all men – were undeniably over-educated and, to me, devastatingly attractive. They all seemed sensitive and friendly. After I knew them for a few months, I realized that beneath the gentility, they were also really, really angry. For example: if, on the way home from a pun-filled evening, they came across computers or TVs abandoned on the street, they wouldn't hesitate to grab a 2x4 and destroy the monitors. At the time, I found this endearing, but in retrospect, those were some hostile fellows.

Anyone who dated in a major city or college town from 1993 to 1999 will recognize the type. For several years, McSweeney's smugly epitomized a culture with its own language (too smart for pop culture), style (too smart for fashion), and social schematic (too smart for anything remotely overwrought). On all scores, in fact, McSweeney's was underwrought, cold and pretentious (but affable about it).

That guy in the club liked me just enough to trade books, to tell me about Will Oldham, to go out for dinner, even to sleep in the same bed a few times, but would never leave anyone with the impression that we were dating. Whatever we were doing, it was in some miserable limbo between platonic and romantic. I tried to talk him into liking me, but that never works, and it really did not work this time.

From what I could tell, most of this McSweeney's-neutered crowd dealt in a similar way with the women in their lives. (At least, I deduced this from the fact that there were no other women around, and that those who came up in conversation almost all seemed to live at least as far away as San Francisco's Mission district.) Still, I'd heard my crush had girlfriends in the past, and I sensed he would have girlfriends again.

A year later, a mutual friend told me he was living with a cute girl with whom he shared a cat. But I never saw that side of him. I was the pathetic friend he saw every other day, the one he would joke about with his real friends. The one who against all reason desperately wanted him.

In frustration, I smoked a lot of cigarettes, drank a lot of deli coffee and slept with his best friend. But nothing had any effect. This was around the time my best friend started to say I was "distant" and "weird" and "why the hell was I so obsessed with that linguist with the squished face."

I was obsessed because he, and McSweeney's itself, had rejected TV-cool, punk-cool, grunge-cool and all other cools to date, and had concocted their own brand. They were emotionless as greasers, jovially homoerotic as beatniks, but smart-assy as old Hollywood stars and at times really, really funny. Their best work was like the greatest note you ever got passed in class.