Daniel M. Lavery wrestles with art and identity

Daniel M. Lavery’s last book, the 2018 short story collection “The Merry Spinster,” was published several days after he came out as transgender. Those stories, rooted in fairy tales and children’s literature and trading in a blend of the wondrous and uncanny, employed a thin veil of allegory to tell a series of narratives about emotional abuse and toxic relationships. Inasmuch as they reflected his personal experiences, it was in the manner of all fairy tales — through archetypes and deep dives into the subconscious.

Lavery’s new book, “Something That May Shock and Discredit You,” pulls away that veil, dealing with his evangelical youth and his life as a transgender man. In pieces that seep through the barriers separating fiction, memoir and cultural criticism, characters wrestle with the consequences of their decisions as well as changes beyond their control. Chief among those characters is the author.

Lavery has long been something of an icon among the young, the book-inclined and the very online. In 2013, with Nicole Cliffe, he cofounded the Toast, an influential and beloved website for feminism, humor and culture writing once cheekily described to me by a fellow fan as “every lesbian librarian’s favorite website.”

His first book, “Texts From Jane Eyre: And Other Conversations With Your Favorite Literary Characters,” built on a recurring Toast feature in which literary figures were equipped with cellphones. Since late 2015, Lavery has been Slate’s Dear Prudence advice columnist, and in 2017, he launched the paid subscription email newsletter the Shatner Chatner, which he maintains today. With the newsletter, Lavery’s writing began to cover his own life more directly.

“Something That May Shock and Discredit You” goes further; Lavery has called it “memoir-adjacent.” Made up of 22 chapters and 19 interludes, the book is a multifaceted amalgam of humor writing, personal essays and ingenious cultural riffs that layers onto Lavery’s frequent preoccupations — biblical stories, medieval romance, Western historical and literary figures, William Shatner — some serious self-examination.

“About six months after I stopped doing the Toast, I started doing the newsletter. I thought I would want to take a longer break, but that wasn’t the case,” Lavery said by phone from Brooklyn, N.Y., where he recently moved from Oakland with his wife, author and academic Grace Lavery. “I found that I was often writing about the response to my body, to my face, to my appearance, to how I felt about changes in my appearance, to what extent those changes felt satisfying or dissatisfying. It was clear to me that this was something that was on my mind a lot … Everything I tried to write ended up being about this.”

That is not at all to say that the new book is entirely personal — only that it arcs toward the writer himself. In these pages, Lord Byron insists he is totally over his ex but clearly isn’t; Marcus Aurelius worries about what people think of him; and Jacob, before being renamed Israel by a nameless angel of the Lord, is forced to “wrassle till noon at least” before his life changes forever. Jacob and his wrestling match are a common and resonant theme throughout the book.

But it’s the piece “Sir Gawain Just Wants to Leave Castle Make-Out” that most clearly blends Lavery’s two primary modes of historical humor and incisive memoir. Its first section reworks the 14th-century chivalric romance “Sir Gawain and the Green Knight” in the form of a play (in the language of text messages), giving the legendary Gawain an anachronistically neurotic cast as he struggles to take his leave of the Green Knight’s Castle. In the second section, Lavery examines his own first forays into romance, when he was “just teetering on the verge of puberty, between sixth and seventh grade,” and the cultural touchstones that were afforded him at the time.

“Perhaps it would have been better for me if I could have seen the movie ‘Velvet Goldmine’ or heard of the Smiths at that age instead, and transitioned at fourteen,” he writes. “I might have called myself Trenton and had a cis boyfriend at fifteen; I might even today be five foot ten instead of five foot seven and a half inches tall. But I did not have access to ‘Velvet Goldmine’ or the Smiths; I had access to Alannah Myles and Sir Gawain and church and was going to have to make do with what I had.”

Lavery also wrestles with his Christian upbringing — up to a recent incident that transformed his life profoundly yet again. His father, John Ortberg, a pastor at the Bay Area megachurch Menlo Church, was placed on leave from his duties in November after Lavery reported Ortberg to church elders, alleging that he had encouraged a member of his congregation with “obsessive sexual feelings about young children” to continue working with kids unsupervised. Lavery then cut ties with his biological family, and he took his wife’s last name. (His new book is published under his old name, Daniel Mallory Ortberg.)

Two weeks before the book’s publication, Lavery revised his optimistic assessment of his father. “I had to go back and take some things out of it that I no longer believed to be true,” he said. “One of the things that it drove home to me was simply that I often think I have reached the end of knowledge, that I know a situation as fully as I can possibly know it, that there are no future surprises in store for me here, and how rarely that’s the truth.”

Like Aurelius and Byron and maybe Gawain too, Lavery worries about the future, and about what his decisions will mean for the life he will carve out for himself, before he reaches the inevitable conclusion that one cannot cross a river on foot without stepping in.

“I always wanted somebody to just say to me, ‘This is the one that you trust,’ ” Lavery said. “‘This is the choice that you make that will result in absolutely no possible regret. Do this and you’re going to be set.’ And that’s never been how life works, and yet that has never stopped me from wanting that to be the way that life works. And at a certain point in my life, it just became clear that I would rather try [transitioning] and regret it than keep sitting in my room trying to hate myself out of doing it … The possibility of regret no longer terrifies me.”

Maher is the news and digital editor of Publishers Weekly.