photo credit: Jackie Molloy/for The Washington Post
Dear Prudence is sitting in one of those Brooklyn coffee shops where the only two choices for milk are coconut and cashew, talking about what it’s like to take on the weight of people’s problems in a world that increasingly feels like garbage.
“It feels like a small act of neatening that I really appreciate,” says Daniel Lavery, the author of Slate’s Dear Prudence advice column. “In this limited amount of time every week, in this incredibly limited scope, you are going to, to the best of your ability, tend to problems.”
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.
... 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.
...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. (Click here to read the rest of the article.)
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