In 2018, author Mary Karr tweeted about her abusive relationship with David Foster Wallace. This was at the height of #MeToo and cancel culture, where the phrase ‘problematic fave’ was commonplace. Wallace, dead for ten years but still alive in the public imagination, was suddenly brought into the conversation. Wallace’s fans, too, were implicated in his bad behaviour, particularly by their reputation for being ‘lit-bros’. At the time, Grace Chipperfield was writing a doctoral thesis on Wallace, which eventually turned into a collection of essays that reckoned with both Wallace’s complicated legacy and her relationship to him as a fan, a scholar, and a woman. The final essay in the collection was a deep dive into Wallace fandom, and to write this Grace corresponded with members of the Wallace community, including one of its most dedicated and active participants: Matt Bucher. Here, then, is a sample of that correspondence. This essay is a series of letters between Grace and Matt throughout which they consider their moral obligations as fans in the age of the problematic fave.