From the New Yorker obituary for David Foster Wallace:
“In his fiction, he aimed at capturing the authentic rhythms of speech and thought, even when doing so meant breaking the rules of writing (rules that Wallace, an obsessive reader of dictionaries and guides to grammar, was extremely familiar with).”
This brought GalleyCat no end of amusement, although the attorney and legal writing expert we consulted says it’s a perfectly good sentence and the thing about not ending a sentence in a preposition is outmoded. “Rules with which Wallace… was extremely familiar” sounds more authentic to these ears; then again, Deborah Treisman quotes an example of Wallace’s writing later in her article in which he asks, “Do you have your own set of abstract questions to drive yourself nuts with?” And that feels more natural than the “proper” reading would, and the question particularly apt.