Sometimes they’re huge problems that touch on racism or trauma or abuse. Sometimes they’re frivolous problems, about weddings or gifts, that present windows to deeper ones: codependency, boundaries and so on.
The tidying-up of people’s personal lives has a singular appeal to Lavery. Each letter is a story in need of a resolution. Yes, there are real people and real complexities on the other side of the Dear Prudence letters, but the format makes each advice-seeker’s mess seem manageable. “It feels like just great, brief plots that are submitted to, like, a person — kind of at random,” he says, “who then submits, ‘Here’s how I think you should end the story.’ ”
Lavery, 33, is not just a random person. Over the past few years, the story of his life has resembled a series of Dear Prudence letters that Lavery has had to resolve for himself, culminating in a new memoir, “Something That May Shock and Discredit You.” The book is an account of his gender transition, interspersed with the types of satirical essays about literature and pop culture you might have once found on the Toast, the now-defunct feminist website that he co-founded in 2013, when he went by his birth name, Mallory Ortberg.
Dear Prudence, I think I’m trans.
Dear Prudence, I’m in love with my best friend.
Dear Prudence, I think I have to cut ties with my family.
There are no formal qualifications for an advice columnist. There are only informal ones: a deep well of empathy, a strong moral compass, a gift for being succinct without coming off as glib. “Most of us aren’t psychologists. We’re not therapists,” says John Paul Brammer, the advice columnist who writes ¡Hola Papi! for his Substack newsletter (previously for Out Magazine). “We’re your pals at the bar who you can tell your issues to, and we’ll talk you through it.”
Of Lavery, he adds: “Danny has that energy.”
Perspective, too. Lavery is the most notable new figure in a field of advice-givers that has begun to diversify, reflecting an overdue understanding that cisgender white people are hardly the only ones in search of the “small acts of neatening” that columnists can provide — nor are they the only ones qualified to tend to other people’s problems.
Maybe it helps for the advice-giver to have led a complicated life — the kind that exposes you to different people, different problems, heartbreak, forgiveness and grief.
For Lavery, some of the most crucial questions and answers have had to do with family: the one he left behind and the one he has made for himself. His upbringing “shaped me and made me who I am, and I can’t change it any more than I can change another part of myself,” he says.
He pauses to take that back: “Although, I can change parts of myself.”
Dear Prudence, a newly minted New Yorker who came from the Bay Area, is wandering through the Brooklyn Museum, when Bernardino de'Conti's "Portrait of Catellano Trivulzio," stops him in his tracks.
“What a s----y little beard,” says Lavery, pointing out the contrast between the subject’s “great, lustrous hair” and the “faint cloud of mist over his chin.”
His unsparing assessment quickly gives way to thoughtful analysis.
“What feels very transmasculine about this is just like, ‘I’ve got my hairstyle exactly as I want it. And my beard’s not ready for prime time, but I’m gonna pull it out.’ ”
If the Toast were still around, it’s the kind of insight that might have led to an entire post: ‘Transmasculine Beards of Art History.” That was the website’s sense of humor: well-read, absurd, knowing. Lavery created the Toast, with Nicole Cliffe and Nicholas Pavich, in 2013. On any given day, they might have published a literary satire, a gender critique, biblical fan fiction and a fantasia about raccoons. Readers, who called themselves Toasties, felt genuinely bonded by their affection for the website. One Toast fan even donated a kidney to another.
One of the site’s memorable features involved Lavery writing funny captions for old paintings centered on a theme, like “women resting miserably” and “really excellent pointing,” which is why The Washington Post suggested a stroll through the Brooklyn Museum.
Lavery studied English, not art, at Azusa Pacific, a private evangelical university. He was born in Simi Valley, Calif., to Nancy and John Ortberg, pastor of the Silicon Valley megachurch Menlo Church. When he was growing up, Bible stories became his default reference points — and remained so, even as he left behind other parts of his early life.
After college, he wrote for Gawker and the Hairpin before co-founding the Toast and later landing the Slate gig. But literary feminist websites, even ones with cult followings, aren’t typically lucrative endeavors; the Toast called it quits in 2016. It was shortly thereafter that Lavery began having, as he wrote, “a persistent thought, which came on all at once and in a way that suggested it had always been with me: What if you were a man, sort of?”
Walking through the Brooklyn Museum, Lavery encounters a small exhibition titled “A Woman’s Afterlife: Gender Transformation in Ancient Egypt.” Some writing on the wall provides an explanation: The Egyptians believed that when a woman died, she must briefly be transformed into a man to be reborn. “The male pronoun on this woman’s coffin represented powerful magic that caused gender transformation,” reads the text on one display.
Powerful magic would be one way to describe his connection with Grace Lavery, a professor of Victorian literature at the University of California at Berkeley, whom he met shortly before the Toast was entering the loam. They became inseparable. “It was a full-on immersive experience of like, hanging out for hours a day, every day, sharing incredibly intimate stories,” says Grace, 36, a tall, British brunette who dresses glamorously in big sunglasses and fur coats — a complement to Lavery’s holographic fanny pack and deconstructed houndstooth blazer.
They began to speak of their shared desires to transition. Grace, who was assigned male at birth, went first. Lavery followed shortly thereafter, in 2016 (he jokes in his book about a “one-in-one-out policy” for their genders). They married in December.
Writing the story of his transition, Lavery found himself returning to the Bible stories of his childhood: There’s the story of Jacob wrestling with an angel and emerging with a new name, Israel. And of course there’s the Resurrection story. Lavery thought about that one after his transition.
Especially when people would say: “It feels like someone died.”
Dear Prudence's final stop in the Egyptian collection is the Book of the Dead, a collection of spells for the afterlife. "Behold me, I am come," begins one spell. "I have brought truths to you."
The business of bringing truths to modern advice-seekers fell first to one gender, then to another. The earliest advice columns, back in the 17th century, were written by men. Their readers’ questions ranged from relationship advice to scientific inquiry. (“Is it proper for women to be learned?” someone asked in the Athenian Mercury, an 1690s British publication, according to the Atlantic. “We see no reason why women should not be learned now,” the Athenian wokely replied. “For if we have seen one lady gone mad with learning . . . there are a hundred men could be named.”)
As newspapers evolved, “we got this idea that women ought to be the ones who deal with emotional labor,” says Brammer, the ¡Hola Papi! columnist. Their authors mostly reflected the audience of the women’s pages, where they were printed. Until the arrival of Dan Savage’s Savage Love in 1991, America’s most famous 20th-century advice columnists were overwhelmingly middle-class white women, such as Ann Landers and Abigail Van Buren (the pen names for sisters Esther and Pauline Friedman, respectively), E. Jean Carroll, and Judith Martin, also known as Miss Manners, among others.
White women, such as Amy Dickinson and The Post’s own Carolyn Hax, still have the high-profile syndicated gigs, but different kinds of voices have started to emerge in the world of advice-giving. Half of Slate’s roster of parenting columnists are people of color, one of its sex columnists is a gay man, and the other is Stoya, a porn actress. Brammer is gay and Latino. Roxane Gay, who wrote Ask Roxane for the New York Times through 2018, is a bisexual black woman who has also written about her weight. Cheryl Strayed, who wrote Dear Sugar for the literary site the Rumpus, has been open about her struggles with heroin and poverty.
Advice readers are Slate’s most loyal users, according to Bill Carey, senior director of strategy at the website, and Dear Prudence gets the most traffic of any regular feature. Lavery receives nearly 300 questions a week.
Many of them are entertaining questions having to do with what Lavery calls the “rich tapestry” of life — a phrase he’s applied to scenarios such as a woman who takes her cat to raves and a man who caught his teenage daughter having sex with her boyfriend while the boyfriend was dressed in a “Mrs. Claus” costume.
In the past few years, Lavery has noticed an uptick in questions about transitioning. He sometimes might answer based on his own experience, but more often the answers are about basic boundary-setting. “If their problem is the way that they’re being treated by the people in their lives,” he says, “I’ll have a baseline of, like, I think you have the right to expect this or ask for this.” It’s reasonable, for example, to tell your family to call you by your chosen pronouns or your new name.
Then again, Lavery’s own experience has taught him that there are limits to what you can expect from family.
Dear Prudence is choked up. He's thinking about his parents, Nancy and John Ortberg. A month before his wedding, he asked them about something that happened recently at the family's church.
According to Lavery, they gave some very bad answers.
A parishioner at the church, who volunteered with children, had told the Ortbergs that he (the parishioner) was attracted to children. The Ortbergs had then allowed the volunteer to continue to work with kids because he assured the pastor that he had not acted on his attraction, a church bulletin explained.
Lavery declined to comment on the situation, but on Twitter he posted a summary describing a conversation he and Grace had with his father about the incident. “We were told (1) that pedophilia was like homosexuality, (2) that the most important thing was maintaining secrecy around this affair, and (3) that we lacked standing to offer an alternative form of treatment for sexual obsessions with children because of our transitions,” Lavery wrote.
John Ortberg did not respond to The Post’s requests for comment.
The Laverys reported John Ortberg to the church when he declined to disclose the details himself. Ortberg took a leave of absence from the church through Jan. 24. An independent investigation “did not reveal any allegations of misconduct,” a church spokeswoman wrote. “In addition, we are reviewing our protective measures for children.”
Lavery had worried about losing his family when he transitioned. He hadn’t; Nancy had attended to him after his mastectomy, he wrote in his newsletter.
But now, “It was very, very, very clear to me what needed to happen,” Lavery says. “It was hard, but not complicated.”
He dropped his last name and cut off contact with his family.
“I wanted . . . to transition out of my bloodline and body entirely, to appear and become inhuman — covered in eyelashes, maybe,” Lavery wrote in his newsletter.
He had advised readers seeking to leave their families before, but he comes to it now with “a newly heightened awareness” of the costs.
“Even if you have total clarity on your side,” he says, “there can be a counterweight to that choice — that afterwards, the momentum slows down and the heaviness and grief, or even a sense of guilt, can settle in.”
The day after their wedding, the Laverys decamped across the country to New York. They now live in the kind of unrealistically nice New York apartment that usually only exists on TV: crown molding, a massive walk-in closet, sweeping views of the Manhattan and Brooklyn skylines that only grow more spectacular when the sun sets. After the year they’ve had, it feels like kismet — “Trading a family for an apartment,” Grace jokes, bitterly, over a cup of tea at their dining room table. The past two months have been among the best of their lives, and also among the worst.
Life is a rich tapestry. Getting through it can take powerful magic, huge acts of transformation and small acts of neatening. Even good counsel can lead to messy resolutions. But sometimes, that’s how a story ends.