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This long thing I’m 90 % done with — I wanted to make a kind of contemporary Jamesian melodrama, real edge-of-sentimentality stuff, and instead I find it buried — like parts of “L.E.A.”—in Po-Mo formalities, the sort of manic patina over emotional catatonia that seems to inflict the very culture the novel’s supposed to be about.6

He added, “I have never felt so much a failure, or so mute when it comes to articulating what I see as the way out of the ironic loop.”

That fall Wallace asked Moore to look over the manuscript and see whether the cuts Pietsch had wanted in June made sense to him. He was pleased when a month later Moore responded with suggestions for more modest condensing. Even better, his ideas were, by Wallace’s estimate, “80 % different from Little Brown’s, meaning I get to go with my gut more.” Wallace’s gut was that when Pietsch read all the pages he’d see better how they all fit together. He had also realized by now that he was not going to be able to get the book in by the end of the year and had apologetically asked Pietsch for an extension; there were only so many hours in the day. As a professor, he penalized students for late papers, but to his surprise, Pietsch was happy to give him more time. “The trick in a case like this,” Pietsch wrote back, “is to make sure we have to ask for only one extension.” They agreed in the end to a new due date of April 15, five months away. Still, feeling guilty after the fact, in January, Wallace sent the excuses he ought to have put in the first note: the surprising Illinois cold, a lithium battery in his 1980s-era computer so old it was “no longer manufactured outside like Eastern Europe,” and most of all Jeeves:

I thought getting a puppy would make it easier to spend 3 or 4 months in high-stress isolation, but it turns out the puppy does not go into suspended animation or reversible coma when I need to work, and shits about 17 times a day, and barks.

He was back at work by now, among other things expanding the “interAmerican huggermugger” that Pietsch had found too complicated, believing that the book needed it. Infinite Jest might be a “Jamesian melodrama,” but it was also the big shit he’d been working on for almost ten years, his bid for a seat at the table with Pynchon, and for that he had to preserve his unfamiliar political setting. He also around this time wrote what would become the beginning of the novel, the memorable scene, set a year after the end of the rest of the book, in which Hal Incandenza has a nervous breakdown during an admission interview at the University of Arizona. What transpires is an exaggerated version of Wallace’s own experience on his college tour fifteen years before, when he threw up at his Oberlin interview. At his own interview, Hal is seized by terror and literally can no longer speak. He is rushed to an emergency room in the midst of a psychotic episode, the end of which trip he imagines in detaiclass="underline"

It will start in the E.R., at the intake desk…or in the green-tiled room after the room with the invasive-digital machines; or, given this special M.D.-supplied ambulance, maybe on the ride itself: some blue-jawed M.D. scrubbed to an antiseptic glow with his name sewn in cursive on his white coat’s breast pocket and a quality desk-set pen, wanting gurneyside Q&A, etiology and diagnosis by Socratic method, ordered and point-by-point. There are, by the O.E.D. VI’s count, nineteen nonarchaic synonyms for unresponsive, of which nine are Latinate and four Saxonic…. It will be someone blue-collar and unlicensed, though, inevitably — a nurse’s aide with quick-bit nails, a hospital security guy, a tired Cuban orderly who addresses me as jou—who will, looking down in the middle of some kind of bustled task, catch what he sees as my eye and ask So yo then man what’s your story?

Wallace saw that the scene was a better lead-in for the novel than the discussion between Hal and his father posing as a professional conversationalist that had stood at the book’s beginning for so long. It captured the sense of terrified isolation that is key to the story, the worry that what we feel we can never express. And it held out a hope rarely signaled in Wallace’s earlier work but dear to his recovery experiences: the possibility that telling a story can heal.

But beginning the chronology of the book a year after the earlier draft had ended also presented a problem, one that offered an opportunity that excited Wallace. Telling Pietsch about it was likely the real purpose of his letter complaining about Jeeves. Wallace acknowledged as much in his note: “A lot of this is stalling before a query.” If Hal was a crack-up in the first scene of the novel, the reader might reasonably wonder how he had gotten that way. There were several possibilities. Hal may have seen the devastatingly absorbing video his father made or be detoxing from marijuana or have taken a potent kind of hallucinogenic fungus known as DMZ (nicknamed “Madame Psychosis”). Hints for all three of these plot twists are in the text. But Wallace wanted to tell Pietsch that he was never going to let the reader settle on one. Infinite Jest was meant to be a failed entertainment, not a potted amusement. He now warned his editor that he wasn’t going to tie up his story in a nice little bow: “Any sort of conventional linear ending for this stuff is in my opinion going to seem either linearily thrillerish in a way that doesn’t go with the rest of the book; or else incredibly prolix and complicated.” Reminding Pietsch that the plot of the book he’d bought “has always been more of an arc than a terminating line,” he proposed

an almost Artaud-ish blackout-type ending…. One that might look truncated or even violently ablated…. That is to say (I am not at my clearest on this, I know), a conceived ending that’s not so much anticlimactic as aclimactic? I can (but hopefully will not) give you about 4300 thematic/theoretical reasons why an aclimactic close here will be best — e.g. resonating echoes w/themes of stasis, annulation, paralysis, undecidability, clarification of questions > solutions to questions etc.

Wallace had dealt with enough New York editors by now to worry how such high-concept talk would strike even the supportive Pietsch. He asked for help, reminding his editor that “your loyalties to readability and readerly pleasure are one of the reasons why your editorial input here and elsewhere is of value.” There was an element of flattery here — Wallace played tennis in his letters too — but also truth. He so much wanted to help the reader to a more engaged life that he feared losing him or her on the way. He went back to writing and rewriting, cutting and then adding back in more than he had cut, taking breaks only to teach his classes. He could not have worked harder, as he let Pietsch know, but even so, he saw he would not finish the manuscript by April 15 and asked for more time at the beginning of that month. His letter requesting an extension was penitent, whether from exhaustion, memories of his tangle with Viking Penguin, or the usefulness of imagining Pietsch as an unforgiving authority figure so he would get the book written:

I’m mortified to have essentially lied to you about 4/15; the date seemed an almost GOP-ishly staid and conservative projection back in January. I now want to say late April or May. I’m not saying this: I’m saying I want to say it. I canceled class for these two weeks, but now I know I won’t be done by 4/18, and then I have to make up all the classes I’d canceled.

He imagined apocalyptic consequences to being late connected to the meaning of April 15:

If I don’t file my taxes I might go to jail — though this is also a sort of late-night terror I have, about Little Brown’s parent company’s lawyers sending me to jail because of some Kafkaesque boilerplate clause I neglected to see at the bottom of the legal document I know I signed, and was given $ by you guys. I know this is just a dark fantasy.