Help! I Couldn't Stop Writing Fake Dear Prudence Letters That Got Published

It was a fulfilling creative outlet, until one got featured on Tucker Carlson.

Bennett Madison
inherent advice

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.

After a few false starts, I learned that a good letter is defined by two opposing values: it must be plausible, but it must also be ridiculous. This is a delicate equilibrium to manage, and one that I botched frequently. Help! My Friend Thinks I Am Stealing Vaccines From African-American Grandmothers To Attend Sex Resorts ran, but was a disappointment; it needed another flourish of insanity to justify its existence. My Family Used to Call Me Auntie Christmas. Now They Call Me the Christmas Karen! was a personal favorite that never got published, likely because it failed on plausibility — I had miscalculated the relative ages of the characters, and the whole thing fell apart upon examination.

My biggest weakness was dialogue. I was always tempted to include fabricated direct-quote diatribes in my letters, even knowing they would raise red flags. In Help! I Refuse to Return My Lesbian-Identifying Ex-Lover’s Moose-hide Vest, I couldn’t bring myself to kill the line where a crusty lesbian elder traumatizes a roomful of young tenderqueers by demanding that they “belly up to the beaver buffet!” This one, sadly, never saw the light of day.

When they did run, my letters were often edited in ways that I didn’t care for. Spelling or usage errors and malaprops were key to the voice of my characters, but they usually got corrected before publication. Help! My Husband and I Can’t Agree On What To Name the Baby We Might Get! was a pleasant exception: it was important to the story that this fictional couple was “getting” rather than “having” or “adopting” a baby, and my word choice was thankfully allowed to prevail.

But sometimes my work was altered in ways that changed its substance. In My Daughter Is Pretending to Be Demonically Possessed… and I Can’t Take It Anymore!, I’d made a point of establishing that the advice-seeker fears dampening her daughter’s creative spirit by scolding her for crab-walking around the house and spitting on her family members. When the letter finally made an appearance on Prudie’s podcast, it had been stripped of its caveats to allow Prudie to deliver a sermon about nurturing childhood creativity. (“This child is perfect, and has a great big imagination.”) I don’t have a child, much less one who’s a vessel for a demon; nevertheless, I felt misunderstood.

Prudie’s advice often missed the point in favor of discursing on pet topics. In Help! My Sister Is Convinced She’s an Unrecognized Genius, and It’s Tearing My Family Apart!, a woman has turned into a monster after getting a perfect score on the type of Facebook quiz that asks users to identify sushi’s country of origin. “IQ. Fake and racist,” Prudie responded. True, but what did that have to do with anything?

Occasionally, though, Prudie praised me: My Mother Is Trying To Convince the Guests At My Gay Wedding To Come Dressed As Disney Characters was, in the columnist’s words, a “beautifully written” letter in which “every turn of phrase was a joy.” The pride I took in such accolades was, I’ll admit, rather unseemly. I couldn’t handle the scoldy gaze of the Young Adult Goodreads machine, but I had missed the bright lights of the trade reviews and their attendant stars. I would take what I could get.

Though I assumed that thousands of people were reading my Dear Prudie letters, I received little in the way of feedback, other than from the small but prolific group of weirdos that populated the comments section of the site and a few close friends who mostly seemed confused about what I was doing with my life. It was the sound of one hand clapping.

It was ironic, then, that the letter that received the most attention was also my final one. The evening after Help! My Husband Won’t Remove His Mask, Even For Sex! ran, I was on my first margarita at a Mexican restaurant when a colleague texted me that it was getting traction on Twitter. I was on my second when another friend alerted me to the fact that the letter had been picked up by Tucker Carlson on Fox News. In a segment with Clay Travis — Rush Limbaugh’s replacement — Carlson read smirkingly from my work over a chyron that read TERRIFIED LIBERALS KEEP THEIR MASKS ON DURING SEX.

The attention was obviously thrilling, but it also made me uneasy. I had meant the letter as a mild comedy of manners set in the neurotic milieu of the Brooklyn middle class — a milieu that was, of course, my own. While part of me was excited to have duped a dweeb like Tucker Carlson with such an obviously phony scenario, I was disturbed to have provided chum for the pro-Covid, bleach-drinking lunatics in his audience. And unless I decided to remove my own “smelly and soiled” mask and reveal myself, no one would ever even know that Carlson had been taken in.

This bittersweet success came at a moment when I was already contemplating retirement. Daniel Lavery had hung up his Prudence hat after taking a $430,000 advance to write about geese on Substack in early 2021, and the news depressed me. I had come to see Lavery as something of a Javert figure (or was he Valjean?), and I was uncertain whether my game would be any fun without my familiar nemesis. On top of that, fake scenarios had started to feel passé. On Twitter, a steady stream of artlessly ludicrous Am I the Asshole? crossposts from Reddit regularly garnered thousands of faves, making me feel undervalued in my own labors. I had grown disillusioned with YA after it had been invaded by an army of carpetbagging would-be screenwriters, and my replacement hobby was being similarly colonized by people who didn’t seem to take any of it very seriously. Now, Tucker Carlson made me consider that what I thought of as harmless trolling might actually have evil consequences.

So I quit the game. Or, at least, I’ve yet to submit a letter to the new Prudence, Jenée Desmond Harris. Maybe I’ll get back to it someday, or maybe I’ll find undiscovered territory from which to operate in a new kind of obscurity. Several friends have suggested that I gather all my work into a collection, but I don’t see the point: when the fakery is advertised, it loses its power. Maybe I’m the only one who thought it had any power to start with.

I wonder often about others like me. I know they’re out there — I can spot a fake from a mile away, but not having gone to Yale, I have no way of connecting with this secret brotherhood. Who are they and what do they care about? Why undertake this calling? I can speak only for myself: at a moment when stories increasingly serve as delivery mechanisms for moral and political messaging, it felt like a tiny form of resistance to engage in fiction that was at its heart completely pointless. At least it was meant to be. I did it neither for money, nor for glory, but for love.

Bennett Madison is the author of several novels for young people, including September Girls and The Blonde of the Joke.