Genre and Gender Bending Continues for Daniel Lavery

You might want to brush up on Dante, Twain, and Old Testament tales to get the most out of the feminist humorist’s latest memoir and essay collection.


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What’s the connection between the Addams family, the Munsters, and transitioning to another gender? Why is Captain James T. Kirk considered a “beautiful lesbian?” What are Sir Gawain and the Green Knight really up to at “Castle Make-out?”

Those are a mere handful of the topics explored by Daniel M. Lavery, formerly Mallory Ortberg, in his new memoir/essay collection, Something That May Shock and Discredit You. The author of The New York Times best-selling Texts from Jane Eyre and The Merry Spinster, feminist humorist Lavery is back with another genre- and gender-bending book that invites readers to brush up on their Dante, Twain, and Old Testament tales.

Recently married, longtime Oakland resident Daniel Lavery boasts a new surname as he traffics in the classics and grapples with the idea of gender transition after age 30. Lavery spoke of his early years in the East Bay, his love of classic literature, and the difficulties of deciding to transition in a recent interview.

Lavery grew up in California, mostly in Oakland. Asked what he likes about the city, he replied, “The food. The people. The community. The queer spaces. Everything about it is just fabulous.”

He continued, “I really feel a sense of having developed a sense of my peers and my community group in the East Bay.”

Lavery honed his comedic skills at The Toast, a humor website co-founded with Nicole Cliffe. Lavery later established “The Shatner Chatner,” a subscription-based newsletter only tangentially connected to Star Trek.

In 2018, Lavery published The Merry Spinster, a collection of fairy tales re-imagined as fractured fables focused on gender fluidity. Now he dispenses advice at Slate.com under the Dear Prudence byline, both in print and as a podcast.

Lavery isn’t afraid to write about esoteric topics, but he works hard to ensure that the uninitiated can participate in the fun.

“That’s the hope,” he said, “That I haven’t gotten so deeply buried into things that you would need to have grown up exactly as I did in order to want to read this.”

The essays themselves are far-ranging but often concerned with transition issues. Most exhibit some form of bewilderment, as the author explores his ambivalence toward making the change to a masculine body.

He said, “How do I decide that I’ve thought about something seriously enough that I want to make some kind of decision? I often find that I would rather endlessly think about whether I really want something than decide to take an action.”

“What I wanted was for someone to say, ‘There’s exactly one right path forward for you. It will definitely make you feel one thousand percent happier.’”

Many of the essays look back at Lavery’s childhood. “I want to go back to revisit the past, not necessarily to rewrite it but to see if I see things differently now. That felt to me very connected to the work that transition very often does to someone’s life.”

With a new spouse and a new name, Lavery is also leaving the Bay Area, heading for New York City. He seemed excited but admitted there is much here that will be missed, from the hills to the bay to his personal community.

“This is really where I grew up, so I’m going to miss a lot of the people who have known me for the longest parts of my life.”