Wallace continued seeing therapists in Bloomington, partly to try to resolve issues with his mother, partly for his own relationship problems. Worried that he was becoming a stock Romeo, he insisted he was ready for commitment, and for an end to what he called in a later letter “serial high-romance and low-intimacy” relationships that never got truly intimate. Other than the classroom, his favored venue for meeting women was St. Matt’s, the church in whose rectory his recovery group met. His listening skills and his own practiced efforts at self-disclosure often led to breaking the rules against “thirteenth stepping.” Other recovery members warned him to stop, citing the emotional dangers of dating the newly sober, which, from his crazed relationship with Mary Karr, Wallace was no stranger to. “The odds are good but the goods are odd,” went an old recovery saw. But Wallace could not stop himself. He wrote a friend that there were times he’d walked into the twelve o’clock recovery meeting and found that he had slept with three of the ten women there, “and come close” with one or two others. His behavior seemed, even to him, at times hard to justify; he was leaving a lot of hurt in his wake. But his bigger worry was that all this seducing was most damaging to himself. He saw that the need to make every woman fall madly in love with him had made him highly manipulative, a man who went around trying to make women feel the same, as he put it in a letter to a friend, “tuggy stuff” he always felt in that moment. To him this was the most wretched of transactions — tricking someone into needing you by pretending to care. It was the thing he had written Infinite Jest in part to expose. It made you, he realized, not so different from “the people selling Tide.”
By the time Wallace returned to Illinois State from his Supposedly Fun Thing book tour in the spring of 1997, he was already worried about his fiction writing. Predictably the effort to produce Infinite Jest had left him feeling wrung out. This sense of depletion had not surprised him at first. He had crafted the beginning of the novel in Boston in the early 1990s, expanded and improved it in Syracuse, and by the time he got to Bloomington in July 1993 he was mostly rewriting and responding to Pietsch’s edits. That had taken up the next year or so. But by 1995 he had been hoping — expecting — to start something else. It was his assumption that the new thing would be a novel too. The novel was the big form, the one that mattered, that reviewers and other authors cared about and by which he could fulfill his compact with readers. DeLillo’s published writing consisted almost entirely of novels; so did Cormac McCarthy’s.
The freedom success now brought left Wallace uneasy; in his life, he had worked to narrow his choices, to give himself a simple set of instructions — don’t drink or smoke pot; don’t try to impress others to make yourself feel better. But on the page things were more complex. He knew that he had to write for himself and not think about the reader, but that was easier to enunciate than to enact. He would have conversations during this period with Costello where he would complain about how hard it was now to get the words down in the right order. Since Amherst, he and Wallace had had as a touchstone of good writing John Keats’s poem “This Living Hand”:
This living hand, now warm and capable
Of earnest grasping, would, if it were cold
And in the icy silence of the tomb,
So haunt thy days and chill thy dreaming nights
That thou would wish thine own heart dry of blood
So in my veins red life might stream again,
And thou be conscience-calm’d — see here it is—
I hold it towards you.
Wallace would talk about wanting in his writing to “make the hand come out,” and then, in disappointment afterward, “The hand, Mark — there’s no hand.” Costello worried that his friend was being too negative about his own work, that success had tipped his delicate internal balance.
When Infinite Jest was done, Wallace found himself more comfortable with shorter fiction. The value of this writing was unclear to him, though, and did not make him feel he was using his time well. “Writing is going shittily here,” he wrote to DeLillo in September 1996. “I’ve spent all summer doing dozens of obscure ministories that seem neither comprehensible nor interesting to anyone else.” He told Brad Morrow at Conjunctions that he spent his days in his black room, writing “weird little 1-pagers.” Some were about “the spiritual emptiness of heterosexual interaction in post-modern America,” as he would phrase it in a later interview, others almost metaphysical aperçus about the hazy intersection of cognition and the world, vignettes he grouped together under the heading “Another instance of the Porousness of Certain Borders.” What had made the scope of his imagination contract so radically? He blamed himself, rather than, say, fatigue or age. He thought perhaps other authors had less trouble. The year before he had turned back to the writer whom he most admired for help. He had a “jejune” question for DeLillo — like “some kind of tentative hand in the back row of a writer’s classroom visit or something.” He went on, “Do you have like a daily writing routine? Do you set off certain intervals as all and only time for fiction-writing? More important, do you then honor that daily obligation, day after day? Do you have difficulties with procrastination/avoidance/lack of discipline? If so, how do you overcome them?”
I ask because I’m frustrated not just with the slowness of my work but with the erratic pace I work at. And I ask you only because you seem at least on this end of the books, to be so steady — books every couple or so years for over two decades and you don’t seem to have an outside job or teaching gig or anything that might relieve (what I find to be) the strain of daily self-starting and self-discipline and daily temptations to dick around and abandon the discipline. Any words or tips would be appreciated and kept in confidence.
DeLillo wrote back to reassure the thirty-three-year-old Wallace that centering yourself to write got easier over time, though it never got easy. “The novel,” he wrote his younger friend, “is a fucking killer. I try to show it every respect.” This perhaps satisfied Wallace for a time, but his hand was up again a month later. Why, he asked his adopted role model, did the route to maturity have to be such a struggle?
Maybe what I want to hear is that this prenominate war is natural and necessary and a sign of Towering Intellect: maybe I want a pep-talk, because I have to tell you I don’t enjoy this war one bit. I think my fiction is better than it was, but writing is also less Fun than it was.
“All right,” DeLillo replied, a bit more sharply this time, “your first book was more fun but that doesn’t mean you’ve left pleasure behind forever.” For him, at least, it was the act of writing that carried him forward: “I have fun when I find myself gliding on language and when the story seems to drive itself forward and when I’m able to give a character his or her most unexpected expression,” he wrote. Still, novel writing, with its isolation and the uncertainty about what one had achieved, was never going to be a picnic. Wallace had to understand that. He offered a kind of buck-up, disputing Wallace’s distinction between his “bad” early work and his “good” later work: