Originally published in Brief Interviews with Hideous Men. Personal enjoyment rating (out of 100): 92.
As a fiction writer myself (specifically an unpublished fiction writer), I am RIGHT THERE with Wallace's self-professed "honest" struggles to salvage the metabelletristic fiasco of these eight pop-quiz interrogations (only three of which he's actually included, a fourth of which is a revision of one of the earlier pieces) by introducing a "ninth" pop quiz that begins as such: "You are, unfortunately, a fiction writer. You are attempting a cycle of very short belletristic pieces, pieces which as it happens are not contes philosophiques and not vignettes or scenarios or allegories or fables, exactly, though neither are they really qualifiable as 'short stories'..." Through the duration of this lengthy and heavily annotated "final" quiz, Wallace stresses the importance of honesty, that being the key that will save the story from being simply a "cute formal exercise in interrogative structure and S.O.P. metatext." He also points out the thin thin line on which the story skates, that it must be
...both grotesquely funny and grotesquely serious at the same time, [lest] any real human urgency in the Quiz's scenario and palpations is obscured by what appears to be just more of the cynical, amusing-ourselves-to-death-type commercial comedy that's already sucked so much felt urgency out of contemporary life in the first place...
Yes, this point's been made in Infinite Jest, but given how raptly readers have been poring over interviews with Wallace's editors and colleagues circa that 1994 publication, they might just as well hear it from the self-conscious author himself, some five years later. The internal struggle of the author is on full display here, and although it does sometimes tip too far into manipulation or "ironic undercutting" -- particularly in the footnotes warning us about the use of terms like "relationship," "to be," and "feelings" -- these flaws are what we're being asked to empathize with in the first place, re: the whole interrogatory quiz structure, and the more he (= Wallace) contorts to himself understand what he cannot find a way to write, the more he, in his unclear clarity, succeeds in convincing us that there is in fact something to be salvaged from his failure.
You could see something near religious/messianic in this, if you wished, the whole Author nakedly suffering for us situation, something coyly hinted at with this line: "you will have to puncture the fourth wall [among other things you'll have to puncture]." Here it is again, the author speaking of his own desperation:
It's going to make you look fundamentally lost and confused and frightened and unsure about whether to trust even your most fundamental intuitions about urgency and sameness and whether other people deep inside experience things in anything like the same way you do . . . more like a reader, in other words, down here quivering in the mud of the trench with the rest of us, instead of a Writer, whom we imagine to be clean and dry and radiant of command presence and unwavering conviction as he coordinates the whole campaign from back at some gleaming abstract Olympian HQ.
And isn't this, in the end, why so many of us love him? Because he was right there with us, more obviously so as our stand-in in his essays, but also struggling within the boundaries of his own signifying fiction? Because it was his wavering conviction, his lack of perfection that made his ideas seem all the more rational and approachable? Yes, as a result of his struggles, we had to wrestle with his text, too, particularly in the pop-quiz portions (4, 6, 7, and 6a) that preceded this one (9), but this is the whole point. Or as Y puts it to X, who has just confided his feelings of "self-loathing and -urtication":
But X, by finally resorting to having Y conduct a thought-experiment in which Y pretends to be X and ruminates aloud on what he (meaning Y, as X) might do if faced with this malignant and horripilative pons asinorum, gets Y finally to aver that the best he (i.e., Y as X, and thus by extension X himself) can probably do in the situation is simply to passively hang in there, i.e., just Show Up, continue to Be There...
In other words, only by having us pretend that we are these characters (such as the "two late-stage terminal drug addicts" who show one another a real human kindness in the freezing alley, or the formally poor mother who gives up primary custody upon her divorce in order to insure that her child has a made-for-life trust fund), can Wallace begin to convince us of the internal sameness that he's convinced we all share. This sameness, incidentally, is the self-obsession/-consciousness we have w/r/t being liked and loved by those around us, a fact that if we openly faced instead of building defenses around, might actually allow us some true happiness and connection in this world. And so it's here, in "Octet," that Wallace pulls together all the loose threads of the short shorts in this collection (many of which I'd argued were not, in fact, short stories), and snatches victory from the jaws of defeat.
Those who believe Wallace to be nothing more than a stunt-writer, a postmodernist, aren't reading deeply enough into a story like this; they're greedily lapping up the flaws and contradictions as a way of excusing themselves from the real honesty that a participatory story like this requires; they're stepping back from the trying, failing, and trying again that I, as a writer myself, feel reinvigorated by. Let's get lost together.