I’m taking up a whole table in a crowded coffee shop, by myself, which is embarrassing but also auspicious, because I’m meeting Daniel Lavery to talk about his newest book, Something That May Shock and Discredit You (Atria, February 2020). “It’s a book with a lot of embarrassment at the core,” says Lavery, when he arrives. “A lot of my work pre-transition was characterized by finding a moment of embarrassment, but I would end it there. So we can all say, ‘It me, this happens to me too, isn’t this embarrassing, let’s all link arms and walk away.’ This book is more, ‘Oh, I found something embarrassing? I’m going to take a bath in it now.’”

Lavery writes advice as Dear Prudence for Slate, founded the hilariously feminist website The Toast, and has two previous books, Texts From Jane Eyre and The Merry Spinster. (His current name is Daniel M. Lavery, Shock and Discredit was released under the name Daniel Mallory Ortberg, and you’ll find other writings under his middle and former last name). Combining memoir with experimental form, the book’s 22 chapters explore his process of coming out as a trans man after being a successful “funny gal” online (“bet I won’t fuckin’ turn into a dude!” he joked, a mistaken prophecy), common cis reactions to transition, and his relationships with community, friends, and family. Twenty interstitial interludes span musings on his body, humorous (“How I Intend To Comport Myself When I Have Abs”) and/or mournful (“Nora Ephron’s I Feel Bad About My Neck, Transmasculine Edition), his relationship with William Shatner (“Captain James T. Kirk Is a Beautiful Lesbian, and I’m Not Sure Exactly How To Explain That”), and Anne of Green Gables.

I marked one line, “the natural transmasculine condition is one of embarrassment,” with a Post-it labeled “FUCK YOU,” feeling personally called out. But Lavery thinks that embarrassment is central to this experience. “I think there’s something particular about white transmasculine embarrassment,” he theorizes. “Some sort of identification with white men is baked into the premise. Embarrassment has to come into it.”

But being conscious about this embarrassment adds something special to his work. In Interlude XVI, “Did You Know That Athena Used To Be a Tomboy,” Athena, a chorus, and a deuteragonist work together to convince “you” not to transition, using arguments that Lavery struggles with at length in the work. But another underlying theme is that Lavery, a 33-year-old trans guy from the internet who just moved to New York from Berkeley, seems part of a unique generation. He’s new to identifying as trans but also deeply aware of his newness. “Having come from a world of feminist blogosphere, where we know the clichés that we want to avoid…I went into it with a real sense of the pitfalls I could fall into.” Like a transmasc Athena, fully kitted in a chest binder, sprung from the collective skull of the trans community.

Lavery admits that “some of the reactions that I got both before and after the book came out were, like, ‘You came out five months ago, sweetie.’” (This interviewer transitioned 13-ish years ago). “And it’s true! I was very aware going into it that this is going to be an early transition book, and early transition is sometimes something that I want to rush through as quickly as possibly, or quickly disavow. Like, ‘Wasn’t that sweet and funny, that was my puberty, luckily now I’m Victor Garber and I’m 57 and welcome to my home, I have a blow-dryer in my guest bedroom.’”

And yet this is where much of this book’s brilliance comes from. Trans memoirs usually have a starting point and an end point, with some narrative of identity holding the story together. Lavery does something more difficult—weaving together absurdity, intense emotion, snippets of biography, and flights of fancy into something that has no center but manages to hold so much, so well. He wants us to “think about early transition in a way that’s not just like, cover your shame.” That feeling of waving at someone you don’t actually know and pretending you were just scratching your head. The balance he found is to have “one take that’s like ‘Don’t worry about that, that’s dumb,’ but then come back to it and say, ‘It is dumb, and that’s OK.’” Another way he describes his approach is “both get a grip, and also, mourn this.” Which is the only way forward when letting go of one experience to find home in a new one.

Kyle Lukoff reviews regularly for Kirkus and is the author of When Aidan Became a Brother and other books.