David Foster Wallace’s Pen Pal

I feel like it’s not my place to comment, kind of like someone else’s choice to be vegan or drive a luxury car or something. It’s a personal consumption choice & they have their reasons.

If I look at it reasonably, I share being slightly perturbed though like you, I don’t know that I would turn down $75k. If I look at it with my romantic, fictional eye it almost seems like a DFW plot device. You’ve got a talented letter writer who adopted an unending stream of identities in college, found herself in a difficult marriage and began writing an author in the midst of his struggles with powerful demons. They never met and the author terminated their relationship about a year before killing himself.

Years later, her house burns, her husband finds the letters intact and they sell them. Heck, if she bought a sailboat with the money and toured the Mediterranean, it would be a hell of a pitch...

Deep sadness. I don't feel like I have the right to judge or the means to understand her position, but it is sad for me whenever the personal and the sacred is converted to asset. My feelings toward Wallace probably makes the whole deal worse.

The article seemed to portray the letters of being a symbol of a previous pattern of troubling escapism for her, and selling them was a personal affirmation of graduating from that pattern. Such items may be sentimental, but if the sentiments that they hold for you aren't a positive force, then it's better not to keep them around.

There is a certain amount of absurdism that you need to buy into, but once you do there is so much to the book (it's also quite funny). DFW dives into themes of addiction, mental health, modernism, etc. He clearly struggled with a lot of these ideas in his own life, and he captures it so well in the cast of characters he creates. I personally found the first 250 pages a little tough, but once I got through that it became hard to put it down.

It's a rewarding read and surprisingly becomes a real page-turner once you get to grips with the large cast of characters. It's also incredibly prescient in the way that it foreshadows 21st century attitudes about the role of technology and social media in our lives, as well as broader cultural and political attitudes (President Gentle's ran his campaign on the promise "let's catapult our trash into Canada and make them pay for it". Sound familiar?). The book is essentially an exploration of the thin line between desire and addiction, in all its forms – addiction to alcohol, to drugs, to excellence, to winning, to perfection, to technology, to loneliness. DFW nails these various portrayals of addiction and almost any reader will see themselves mirrored in one of the book's characters.

I read it in hard copy and am now rereading on a kindle, and would recommend the latter over the former. The three hardest parts of reading IJ for me are (1) its size (the book is like a brick and the font size is tiny), its vocabulary (DFW frequently uses archaic language and domain-specific jargon or just totally makes up words – about a third of the unfamiliar words in the book aren't in the Oxford dictionary), and the hundred of endnotes which are critical to understanding the book, and which themselves have countless footnotes. The kindle's configurable font size, built-in dictionary, and footnote navigation greatly simplify the process of reading it.

My biggest tip for reading it is to not try too hard to make sense of the plot or characters for the first few hundred pages. It is written in an intentionally difficult style; there'll be a long chapter about an unnamed character, only for that character to disappear from the novel until 300 pages later when they're reintroduced in a completely different context and you might not even realise that this guy is actually the same guy from that earlier chapter. If you enjoy the writing, take it on faith that you'll eventually have a grasp of the plot just enjoy the ride. If you don't enjoy the writing, the book's probably not for you. Even at a brisk reading pace it will probably take two or three months to finish, and by the end it will feel like the book has always been a part of your life.

IJ is also distinctive in that many of its chapters and sections could stand alone as wonderful works of short fiction. So even if you're not sure what's going on or how the characters you're reading about fit into the plot, the writing itself is sufficiently captivating that it doesn't really matter. My hardcopy is dog-eared with sections like these:

* The tragicomic death of DuPlessis (not a spoiler), told in a meandering run-on sentence. "... after unspeakable agony, hearing his head's pulse as receding thunder and watching his vision's circle shrink as a red aperture around his sight rotates steadily in from the edges, at the height of which he could think only, despite the pain and panic, of what a truly dumb and silly way this was, after all this time, to die, a thought which the towel and tape denied expression via the rueful grin with which the best men meet their dumbest ends — this Guillaume DuPlessis passed bluely from this life, and sat there, in the kitchen chair, 250 clicks due east of some really spectacular autumn foliage ..."

* Ken Erdedy's introduction ,which captures the experience of that last desperate substance binge, by an addict who doesn't even get enjoyment from their substance of choice anymore, and in their addict's logic they obscenely think that actually maybe if they just consume a sufficiently large quantity of the subject it will be so unpleasant and disgusting and shameful that they'll never want to consume again. On my first read I didn't even realise this chapter was about Erdedy since he's not named in it. Kate Gompert's and Joelle van Dyne's introductory chapters are similarly impactful.

* An endnote which provides exposition on the background and childhood of the wheelchair assassins, where said exposition is in the form of a terribly-written essay that a teenage student is trying to plagiarise for a homework task. The endnote alternates between the hilariously overwrought text of the essay itself, and the student's increasingly frantic and frustrated attempts to paraphrase it.

* "The so-called 'psychotically depressed' person who tries to kill herself doesn't do so out of quote 'hopelessness' or any abstract conviction that life's assets and debits do not square. And surely not because death seems suddenly appealing. The person in whom Its invisible agony reaches a certain unendurable level will kill herself the same way a trapped person will eventually jump from the window of a burning high-rise. Make no mistake about people who leap from burning windows. Their terror of falling from a great height is still just as great as it would be for you or me standing speculatively at the same window just checking out the view; i.e. the fear of falling remains a constant. The variable here is the other terror, the fire's flames: when the flames get close enough, falling to death becomes the slightly less terrible of two terrors. It's not desiring the fall; it's terror of the flames. And yet nobody down on the sidewalk, looking up and yelling 'Don't!' and 'Hang on!', can understand the jump. Not really. You'd have to have personally been trapped and felt flames to really understand a terror way beyond falling."

* James's father's monologue in the garage, which I maintain is one of the best pieces of short writing that I've ever read. I get actual chills up my spine when I read the words "Jim not that way Jim." It's such a dark and beautiful reflection on ambition and potential and what happens when that potential is crushed. "I know, I know you've seen me brought home on occasions, dragged in the door, under what's called the Influence, son, helped in by cabbies at night, I've seen your long shadow grotesquely backlit at the top of the house's stairs I helped pay for, boy: how the drunk and the maimed both are dragged forward out of the arena like a boneless Christ, one man under each arm, feet dragging, eyes on the aether." Stunning stuff.

For me, I can only read DFW short stories. I love his writing, but, like a very rich dessert, I prefer limited to large amounts.

I don’t know if it is good but after reading it years ago I still think about it all the time. DFW has a lot to say about the realities of how people cope (or fail to cope) with modern society.

Highly recommend reading it in physical form, trying to follow the footnotes on a kindle is a torturous experience.