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    It all started in 1995, when I couldn't get into a Chumbawumba concert on Houston Street in lower Manhattan. I was nineteen 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 twenty-three-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. 

    I realized that beneath the gentility, they were also really, really angry.

    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.

    Comments ( 55 )

    love it. gets some good digs without sounding at all bitter. keeps it real: about youth in general somehow... even though i'm sure it was hard to keep from really having at mcsweeneys. a topic all in itself.

    commented on Feb 14 05 at 1:07 pm

    I was with you there until you cited Wes Anderson as someone who is approaching this "sincerity" as more refreshing--he's part of the same paradigm! And he's rapidly approaching over! (Because The Life Aquatic was the messy fulfillment of the moderately effective yet slightly bothersome twee-ness of The Royal Tenembaums.) In fact, I think you could make an argument for the tiredness of McSweeney's, Wes Anderson, and The Decemberists--although the new album is actually really good because the songs have something at stake. Risk. Vulnerability.

    E.D. commented on Feb 14 05 at 1:17 pm

    I take exception to this article. In the mid-90s, I would have had sex with any woman who asked me to, and probably did. Also, I like sports and I've never heard a Will Oldham song. Not all men are the same.

    --Neal Pollack

    NP commented on Feb 14 05 at 1:54 pm

    Great article.

    RM commented on Feb 14 05 at 8:26 am

    awesome essay, really right on. i went to wesleyan (where eggers is an alumn, i think) and i always felt like the pseudo-sensitive, snarky guys were just our generation's version of jack keroac - distant, self-absorbed, and too detached and lonely to recognize it.

    sd commented on Feb 14 05 at 10:49 am

    I enjoyed the article. It's been what I've been saying all along, except you left this part out--the McS group really don't like non-white people. It extends even to their online publication. Browse the names of the contributors over the years, see how many hispanic, or even italian names you find. Most of the women are girlfriends of McS's males. It's really a disgusting little cadre of nepotism.

    MM commented on Feb 14 05 at 11:49 am

    You should have talked about that one mcswy's groupie who got herself knocked up by one of them on purpose and is now the single mother of a little bundle of proof that one of them once had sex with her.

    M.O. commented on Feb 14 05 at 11:57 am

    This is stupid. What kind of person considers Pearl Jam's fight with Ticketmaster weak?

    se commented on Feb 14 05 at 12:25 pm

    Great. And I see this as a caste system issue. Haven't you the money to be an Ivy League man? Oh, you DO have a bit of money? Well, you're just after us to support you, darling. You want to tag along, as girls will.

    commented on Feb 14 05 at 4:24 pm

    Great essay, Ada. I know those kinds of guys (and some of those actual guys) and I'm familiar with their generally undeserved lady-magnatism. This brings up a related, fascinating conundrum: boy authors reel in the chicks, while girl authors do not reel in the cute boys. Maybe I was naive, but I assumed I'd be fending off adorable, smart skateboarders with beautiful arms once I started publishing stuff. It never happened. Boys are totally unimpressed with girl-talent; sometimes they seem annoyed. Smart does not seem to be sexy on girls. Possibly, it's a little scary on girls. I'd love to read an article by you about that.

    SR commented on Feb 14 05 at 4:26 pm

    Agreed with the poster who says Wes Anderson is in the same boat but think that this article is wonderful. If only that it captures perfectly that feeling of wanting to be a part of something, failing, and then later finding out that that something was stifling and unimpressive to begin with, like McSweeney's. The pseudo sincere, self-indulgent Tom Bissell pieces such as "Perhaps it's best to Teach Them All," reveal themselves with phrases like "Them All."

    S.K. commented on Feb 14 05 at 5:30 pm

    Oh my God! This is the greatest article I have ever read! You hit the nail on the head so perfectly. To update the paraphernalia list of the "McSweeney's wannabe crowd circa 2005" it would include "the exact same timbuktu shoulder bag (the better to accentuate the lazy man-boobs), the same Moleskin notebooks, the same iPod Shuffle, and, if their parents have the means, the same Toyota Prius." Any writer who has submitted to McSweeney's in a moment of weakness, knows that they send the most irritating rejection letters of any "publication." Now lets watch their "clever rebuttals" as they try to circle and attack, all the while averting their eyes from one another's man boobs, timbuktu bag, and ironic children's book reading materials.

    MTA commented on Feb 14 05 at 6:17 pm

    the author of this article comes across as a bit of a rejected lover. It's more sad for her (the writer) than for the emotionally unattached men of her dreams. But is this trifle of an article helps the author move past her feelings of rejection, then bully for her.

    DJM commented on Feb 14 05 at 9:22 pm

    Yeah, it reminds me of what's sure to be the new subject of media conversation, "Bitter Girls" (it's the title of a book about women post break-up), but the value is in telling her "bitter" story so we can read it and remember our own. Isn't it just that simple?
    I just want to disagree with the woman saying we girls don't get boyfans through writing or generally being smart enough. Personally, I have a lovely following of nerds :)

    I. commented on Feb 14 05 at 10:24 pm

    SK, you are a fool. Tom Bissell is the best writer writing today. Dumbshit ULA craphead.

    io commented on Feb 14 05 at 11:10 pm

    IO,ooh is this "snarkwatch?" I have nothing to do with the ULA, I think they can be infantile,are bad spellers, although I agree with their stance on rich writers accepting need based grants, and last I heard, I have a right to express my opinion. I don't like the guy, nor the patronizing article he wrote for the Believer. One can not like McSweeneys and Bissell and not be part of the ULA. It is a possibility. Before you call people names maybe you should think about whose head to whom the crap belongs. Is that what happens now? People get called ULA because they express their dislike for someone's writing? Grow up!

    SK commented on Feb 15 05 at 3:41 am

    thank you thank you thank you thank you thank you. thank you.

    jlc commented on Feb 15 05 at 6:30 am

    Great article. Hooksexup, can we get some more naked men please? I am sick to death of breasts. We women are beautiful, but... naked men, Hooksexup. Naked men.

    commented on Feb 15 05 at 10:19 am

    Ada,

    Bravo.

    You hit it on the head. For so many of us who have harbored a simmering resentment for this class of intense navel-gazers. Who wear their punnery like armor, and brandish moral superiority like a magician's bouquet of flowers.

    They have somehow made it uncool to even try to do what they do. Fortunately, you have not succumbed.

    Can we add Chuck Klosterman to this pyre?

    CB commented on Feb 15 05 at 10:57 am

    hi, i blogged a bit about this good piece--https://regularstaple.blogspot.com/2005/02/heartbreaking-work-of-essentially.html

    sdm commented on Feb 15 05 at 3:16 pm

    Does anyone else find it sort or ironic that the folks defending the McSweeney set, seem to have missed the entire point/premise of the piece?

    af commented on Feb 15 05 at 4:00 pm

    Anyone here have copies of their rejection letters from McSweeney's? Wish I hadn't deleted them, they're a priceless look at the arrogance of those guys.

    -rml commented on Feb 15 05 at 4:04 pm

    I used to be one of those women, too.
    great piece.
    --Elisa Zuritsky

    ez commented on Feb 15 05 at 4:31 pm

    I disagree af. It seems to me the author has missed her own point. She never draws the link between the young, confused, intellectual who has semi-romantic relationships with women, and McSweeney's. Ada's description of this type is interesting, but it could just as easily be the spoken word set in Chicago or the young realist painters in Los Angeles. The man she was in love with is a generic type and an article on that type, as well as the type of women like Ada who fall in love with them, might be interesting. But the attack on McSweeney's, at least within the confines of this poorly reasoned article, is gratuitous.

    dcf commented on Feb 15 05 at 6:28 pm

    DCF, you just proved AF's point! The "guy" she was in love with IS McSweeney's, not an actual GUY, the magazines, the books, the journals, the pompous followers, THAT is what she was in love with. I'm sitting here shaking my head in disbelief. You totally missed it. She's talking about how she got over her fascination with the McSweeney's publications, attitudes, ironies, and self-importance when she realized that it's just a stance, taken in the same way she perceived Pearl Jam, when a personal fan letter got a corporate style, rubber stamp invitation to join the band's fan club. MScweeneyes are the guys with rolled up jeans, feeling too knowing and witty for their own good. She saw through their 2 dimensional pretensions. Seriously, read the sh!t on the Mcsweeneys website, and flip through their books, then read them five years later and see if they don't strike you as weightless and shallow. Heartbreaking Working of Staggering Genius is a prime example, I can't get through the first quarter of it anymore. I pray that Nick Hornby can escape their clutches, but he's getting sucked in, slowly but surely. But as for you DCF, come on, open your eyes to allusions and metaphor. Damn, too literal.

    mta commented on Feb 15 05 at 7:07 pm

    i must say i am torn about this. on the one hand there seem to be a few people throwing stones here whose work has been rejected by mcsweenies. as a magazine publisher i feel an visceral empathy for the publication -- it ain't easy to keep a little literary publication alive, and its unfortunate that rejection letters tend to sew resentment. why do people submit articles to journals they don't care for? seems to me there is a bit of the groucho marx principle at work here, protestations that mcsweeny's if over notwithstanding.

    on the other hand, i agree with the assessment of the publication -- the more ironic than thou game plays itself out pretty swiftly, and is finally a rather cowardly intellectual position.

    ironically the undercurrent of bitterness in the little mcsweeny fiefdom was probably originally catalyzed by smug rejection letters, and now they are writing their own. beaten children beat their children. but you can't publish an interesting publication without rejecting people, and there is a place for gimmicky literary convolutions. this is the crucible phase: will they persevere through the post-limelight era, and discover, as Ada has, the timelessness of sincerity?

    ben commented on Feb 15 05 at 10:41 pm

    Interesting point. I personally feel that McSweeney's slap in the face rejections knocked off my rose colored glasses and I started to think "This bunch is kind of lame. Why did I ever think they were so cool?" In Ada's case, she had them come to her asking for sestinas (a form I can't help but think the editors had only recently "discovered") and she had the good sense to say, "No thanks, doughboys."

    rml commented on Feb 15 05 at 10:51 pm

    Ms. Calhoun,

    Right on, honey. You're really onto something there about the not-so-accidental, male-oriented thing that breathes life into McSweeney's

    A.R. commented on Feb 15 05 at 11:16 pm

    Ada,
    How do you feel about Michael Woolf calling you a "stalker" in his column? I mean, he was talking about you, right?

    PTH commented on Feb 16 05 at 7:09 am

    I received one rejection from McS and it happened to be pretty darn charming and encouraging (the drawing was sweet). That it happened to be written by a woman may make it the exception that proves the rule (or something). Any examples of snark?

    ml commented on Feb 16 05 at 6:46 pm

    I'm a young and impressionable writer who has had the fortune of never dealing with McSweeneys on any level whatsoever (a year ago I would have said "Mc Who?") However, from what little I tried to read of Heartbreaking Masturbation Piece I can see that you have summed up exactly how I've grown to feel about the Eggers and his lot. Really, an outstanding article. I'm just sorry you had to go through all that mental exhaustion. I would like to bid welcome to the "new" generation of whatever writers come next and hope that I can 1) be a part of it and 2) we don't fall into the same bitter/smiley pitfalls of the previous generations.
    Oh, and here's my shameless blog plug: sarasensurround.blogspot.com

    SAB commented on Feb 16 05 at 10:09 pm

    This was the essay I always wish I could write. Thank you for articulating my thoughts and experiences perfectly.

    NS commented on Feb 17 05 at 3:29 pm

    fabulous article!

    haven't we all had wince-worthy crushes?

    honestly. sometimes, i think i should be locked away for my bad taste in men.

    bk commented on Feb 17 05 at 6:23 pm

    SR :

    I'm a guy who's always been very impressed and interested in talented / smart / assertive / successful / confident women .
    The problem with most women of that type is that they are strictly interested in men who are more talented / smarter. more assertive / more successful / more confident and let's not forget older. Some of those cute boys might be the type who would like a smart brainy woman, but they don't feel as smart/accomplished as you are and know that for most women, a less acomplished man is out of the question. Accomplished men, on the other hand, usually have no problem whatsoever with less accompished women.

    HV commented on Feb 18 05 at 1:55 pm

    To the person who commented about the lack of "non whites" :
    It's often assumed in some circles that a lack of "colour" in that particular clique is a result of racism. It doesn't occur to some people that black folks may, in general, not have the slightest interest in said culture anyways .

    HV commented on Feb 18 05 at 2:04 am

    Well done & spot on. ---Sabra Wineteer

    SDW commented on Feb 18 05 at 9:13 am

    I'm absolutely certain that there was no such thing as McSweeney's in 1993. I don't even think there was a Might Magazine in 1993, which seriously calls into question the truth of this article.

    se commented on Feb 18 05 at 4:24 pm

    Uh...Ada said 1995 in the article.

    B.S. commented on Feb 18 05 at 7:00 pm

    from article:

    da commented on Feb 18 05 at 8:43 pm

    Great write Ada. It was enjoyable to read an article that ended on such a high note of appreciating the love you do have. A love that's accepting of his lady instead of some ficititious character he wants her to be.

    - Savannah Skye...

    ss commented on Feb 19 05 at 9:41 am

    SR wrote: "Boys are totally unimpressed with girl-talent; sometimes they seem annoyed. Smart does not seem to be sexy on girls." That's a load of crap. Hooksexup's personals would not even exist if there weren't zillions of guys who like intelligent, creative women. Think about it.

    DGR commented on Feb 20 05 at 1:25 am

    SR: Yes, I recognize that what you said is true of most men. Nonetheless, here on Hooksexup...

    DGR commented on Feb 21 05 at 4:25 am

    outstanding.

    jd commented on Feb 24 05 at 11:27 am

    Ada, great article! I just praised you on King Wenclas' ULA blog:

    https://kingwenclas.blogspot.com/2005/02/hunter-thompson-mystery.html#110...

    I hope this link works. Anyway, great article!

    TH commented on Feb 25 05 at 12:48 am

    Great article, great great great, I remember it all, and they were sort of awful.... But it's a snapshot of an adolescent past, both theirs and ACs. They were boys then, now they're men. (Both literally and figuratively -- and by the way, there were lots of girls around too, some of them even wrote!)
    Sure, the cuteness was unbearable, but both The Believer and McSweeney's -- the publication, not the website-- have outgrown most of their cuteness and put out some great articles, and even better books. Off the top of my head Stephen Elliott, Tom Bissell, Ben Ehrenreich, Neal Pollack and Wiliam T. Vollmann are all excellent writers who have nothing whatsoever in common besides good writing, and publication in McSweeneys.

    So what are we going by here, the book, or the cover?

    SA commented on Feb 25 05 at 9:48 pm

    I just wanted to send Ada three cheers and fists in the air. Her article, with its wry wit and grace, was so spot-on, it made me blink away all the lighters waving in the night I thought I suddenly saw sweeping back and forth in salute.

    hp commented on Feb 28 05 at 10:10 pm

    Actually, I have slept with a McSweeny's writer. No joke. He actually wrote a video game review that was published on The Onion AV Club last week.

    It was just the once, I was 21 and he bought me two kamakazes... but yes, I slept with someone who writes for McSweeny's.

    ksf commented on Mar 01 05 at 3:56 pm

    ada calhoun, your mcsweeneys article made you a minor celebrity/hero at my small liberal arts college when i posted your article in the bathroom stall

    i loved it

    im commented on Mar 01 05 at 4:12 pm

    woah. that essay was so otm it hurts. or perhaps it makes it not hurt so much. the last guy i fucked is actually one of the authors below. and i'm still kinda embarassingly, frustratingly sore about it.

    in an effort to figure out why i was so upset over such a trifle, i obsessed about the chasm between male and female expectations and desires; the nature of art, life, manipulation, and the differences between the 3; the battle between the introspective and the extroverted; whether the noncommittal-seductive push-pull is a subconscious survival mechanism or irresponsible exploitation... and probably a few more heavy theoretical topics. but i dunno if any of that helps. he just had some kind of charisma i'm a sucker for. the unique, intellectual affectations and signifiers those guys work really are confusing. but none of it made me feel very good. women (or maybe anyone with romantic ideals) are so willing to withstand any pain in pursuit of 'love', but there's a difference between working through debilitating issues to get to a greater goal and working through your needle phobia to become a junkie.

    but enough! be done with this!
    and thanks for the essay!
    it makes me feel less insane and alone while i wait for someone much more suitable to come along.

    LC commented on Mar 10 05 at 1:43 pm

    Yes. Yes, yes.

    mr commented on Mar 13 05 at 1:10 pm

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