I couldn’t stop writing fake Dear Prudence letters that got published

From Gawker:

Sometime at the tail end of 2018, shortly after abandoning yet another draft of what was supposed to be my fifth Young Adult novel, I took up a different form of fiction: I started writing fake letters to Dear Prudence, Slate’s long-running advice column.

Part of the reason for this change was that I was getting too old for young adults. As the sun set on my twinkhood, the teenage characters in my unfinished drafts had become suspiciously middle-aged in their preoccupations. They were jaded about sex, fretful about the effectiveness of their skincare routines, and clumsy in their use of emojis. Maybe worse, in the time that I had been writing YA, the once pleasantly eccentric corner of book publishing had become a stronghold for cynical opportunists and people who seemed to despise the very idea of literature. It was all fucking with my head, and while I couldn’t imagine giving up on fiction entirely, I was starting to think that what I had spent my career doing wasn’t working anymore.

Writing fake letters to advice columns could not be considered a good career move; after all, it was unpaid and I wouldn’t even get a byline out of it. On the other hand, it was easy and creatively fulfilling. In my anonymous, fabricated letters to Prudence, I could follow the most demented threads of my imagination without having to anticipate the omnivalent flavors of opprobrium that might rain down on me from YA’s brigade of cultural revolutionaries.

The world of “agony aunts” was not new to me. In my childhood, I would take the Washington Post and the local Montgomery Journal with my after-school snack, and while I’d tried to cultivate an interest in the news of the day, the advice columns were what really spoke to me. Part of this was personal. It was family legend that my grandmother had been published in the 1970s by Ann Landers, sincerely asking if she should divorce my grandfather for his secret smoking habit. Ann had advised her to chill, and they remained married, so I felt that in some way I owed her for my existence. (Then again, my grandfather eventually died from the cigs, so maybe Ann was to blame for that too.) In my pre-teen mind, Ann Landers and her sisters (Dear Abby was, in fact, her actual sister!) were figures similar to the Fates. To contemplate the ways in which their pronouncements had altered the course of history was to stare down a dizzying kaleidoscope of Quantum Leap what-ifs.

I was also intrigued by the question of fakes, for which Ann was always on alert. She operated under the thinking that Yale undergrads were the most common perpetrators of fabulist letters, and, for a time, refused to publish any letter bearing a New Haven postmark. This suggested to me an erotic glamor: I imagined dormitories full of muscular undergrads lounging around in their undies and collaborating on phony scenarios before hitting the showers together to celebrate their labor. It was with this dream in mind that I approached my task.

Over the next couple of years, I used burner email accounts to submit around 25 letters to Dear Prudence, at least 12 of which were answered on either the printed column or the podcast.

Though Dear Prudence has run in Slate since 1997, the role of Prudie was assumed in 2015 by Daniel Lavery — co-founder of the feminist website The Toast and author of a book about famous literary characters texting — who transformed the column into something of a tribunal, doling out po-faced judgment to guilty white cishets for crimes of allyship. Was it wrong for a letter-writer to call the cops when she saw a home invasion taking place on her street? (“You can’t go back in time and undo what you did, of course,” an unamused Prudie tsked.) Would it be morally acceptable for another to steal their parents’ phones and secretly delete objectionable content from their Facebook feeds? (“Go ahead and unsubscribe them with my blessing,” Prudie advised.)

More than being an heir to Ann and Abby, this incarnation of Prudie felt like an heir to Judith Martin’s Miss Manners, whose adjudications on minor questions of polity were, in their own way, more titillating than the seamier stuff offered up in more generalist columns. But rather than looking to Emily Post, Lavery’s Prudie was guided by the convoluted pieties of Twitter. This was fertile soil for the themes that I was interested in, which included Disney monomania, semantic disputes in queer relationships, and paralyzing anxieties around Brooklyn-style social mores.

Link to the rest at Gawker and thanks to D for the tip.