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.

I had exactly the same reaction to McSweeney's at 19 as I did to Pearl Jam at 15 – an urge to write someone a well-composed letter full of brilliant observations about life's subtle ironies, understood by only we happy few. (For the record, I did send one to Eddie, an expertly composed, Selectric-typed, single-spaced page, and got back a corporate-y invitation to join the Pearl Jam fan club.)

I can see now that Dave Eggers and Eddie Vedder were, for all intents and purposes, the same person. Every generation has its aloof, intense objects of anti-pop lust. Both were way too serious for their own good and had a tendency to pick lame fights: Eggers with The New York Times and journalists generally; Vedder with Ticketmaster. Also, most importantly, neither one would date me, I felt sure, even if we met. Both represented everything I ever wanted and couldn't have – and not just because I didn't have a fake ID. I dreamed about Vedder until I got the fan-club invite, then decided he was a hypocrite and grunge was anti-intellectual.

Then came Dave Eggers. While he was similar to Eddie Vedder – both were avatars of an identical impulse – they differed in one key way: Eggers represented the much-headlined New Sincerity. Unfortunately, in the '90s I was about as Old Sincere a girl as you could find. I could not lie, and I could not make it through a Hal Hartley film without weeping at its human truth, although I hated that about myself. McSweeney's writers hated their own feelings too, I was sure, but I couldn't do anything to hide mine, whereas they somehow were able to transmute theirs into jaunty little titter-worthy pieces with titles like "An Open Letter to Little Children Who Play in the Alley and Like to Throw Stuff At My Car."

My friend describes their style as "Inside-jokey, Ivy-League-y, casually banter-y, but referencing every writer of the past three hundred years." In order to participate, you have to have your eyebrow cocked 24 hours a day. Or, as another friend says, "It's like they built a cool treehouse in the backyard but required everyone to invent their own cutesy conceit before they'd allow them up the ladder." Only when you play their game in exactly the right way will you earn love, or whatever passes for love in that sphere.

I never got close enough to find out exactly what that was. Which is why I take some perverse delight in what's befallen the Eddie Vedders and Dave Eggers of our generation. They've become a parody of themselves – the earnest growl now sounds so affected, the Your Disgusting Head books are beyond wearying. And I don't know if there are still people who relate to each other like that: linguistically tap-dancing all the time to earn praise and affection. I know I gave up on it by the time I got out of college. That hyper-smart tone isn't cute anymore. The joke – the ye olde names for everything, the binding in odd countries, the way-limited editions, the show-offy readings – has gotten old. Those guys have gotten old.

I don't know exactly what brought about the end of their era: was it Dave Eggers' egomania, or the fact that Wes Anderson's brand of cute referentialism is fresher (and that Anderson doesn't antagonize the press)? For years, there's been all that talk about sincerity being the new irony and irony being the new sincerity and I don't pretend to have any new insight into which is which this week. All I know is those guys haven't had anything new to say for some time.

I was recently asked to write a sestina for McSweeney's. Flattered, I tried for an afternoon and then gave up. It wasn't that I couldn't produce one – I wrote four poems that were even the traditional iambic kind, but I didn't like them all that much, and to be rejected by those guys again was more than I could bear.

The promise of disapproval just doesn't turn me on like it used to. I no longer revel in the upturned nose of the frigidly pompous that used to get me so hot. Lots of girls I knew (and plenty more I heard about; see Michael Woolf's article "The Kidder King") had similar non-affairs, chasing guys who would invite them to open mic readings but never, ever save them a seat. I think it's a variant of the broader mid-twenties syndrome: shirking commitment in creative ways. But McSweeney's created a virulent strain, a relationship superbug.

These days, I look at McSweeney's like I look at all those guys I was so obsessed with who wouldn't give me the time of day. Just like the eco-feminism books I enthusiastically read in my first year of college. It's not like I don't know what the hell I was thinking. I know EXACTLY what I was thinking. That's why I'm so embarrassed.

The fact is, I should have found someone else to hang out with that summer and all those '90s summers after that, when I instead wasted my time on representatives of the neo-sincere who disdained me: Davide, the 29-year-old virgin so religious he thought he could make it rain by praying; John, the realist painter who introduced me to the Replacements and told me he didn't love me while we sat a foot apart on a dock in the middle of the night. In most cases, I took it well – which is, of course, what neo-sincerity required.

With Valentine's Day upon us, my first as a married grown-up, I've been able to look back on all my wince-worthy crushes with a little distance. It's the ultimate in Old Sincerity: wistful reflection (cue appropriate Cure song). Only I don't feel so wistful about that particular phase – just humbly grateful that I wound up with someone besides those guys I so unproductively swooned over back then. Being with someone who gets worked up about things besides obscure poetry meters and taxidermy is really kind of great. So, An Open Letter to All Those Neo-Sincere Men I Threw Myself At: Sorry, my mistake.

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