Rejecting the suffering bildung often demanded of transgender writers, Ortberg’s narrative is anything but linear: It skips back in time to mythic Greece, traipses across the landscape of contemporary pop culture and, in one wonderfully fabulist entry that would make Carmen Maria Machado proud, slips outside of time altogether ... Such temporal vertigo makes Something That May Shock and Discredit You addictively strange and delightful ... Ortberg partakes of neither the damaging trope of tragic transness nor the sentimental sanctimony that we are 'permitted,' offering instead the comic and the transcendent. As he confides, 'I have been a mystery, and I have been changed, and I have been first natural and afterward spiritual.'

Daniel Mallory Ortberg’s Something That May Shock And Discredit You is three eloquent books in one: memoir, essay collection, and treasure trove of cultural analysis, all coming in under 250 pages. Ortberg is as nimble a storyteller as they come, so the shifts from painful personal revelations to pithy observations about Lord Byron turn on a dime while still mostly feeling part of the same whole ... The details are all Ortberg, as is the ability to turn eschatology into something more accessible and less judgmental; but the vague sense of dread that comes with puberty, spurred on by one’s growing awareness of the world, is universal. Such admissions are woven throughout the book, deployed with Ortberg’s searing wit and deep knowledge of TV, film, scripture, and Bulfinch’s Mythology. ... more a work of great perspicacity than one of empathy, though it is certainly compassionate. But just because we feel spoken to by this book doesn’t mean we are being spoken for; as insightful as Ortberg remains about literature and media and the human condition, he’s created a deeply personal language for a deeply personal story.

A...kind of glee animates Ortberg’s writing, and it rushes all the way through this thoughtful, joyous book. Even when Something That May Shock and Discredit You delves into difficult material...Ortberg always writes with a sense of profound and honest delight: What luck, it’s another day where he gets to be a man. And reading, you can’t help but be delighted with him ... This book is odd and self-satisfied and bizarrely specific, in all the best possible ways. Consistently, it’s funny ... But Something That May Shock and Discredit You is also tenderly, gently thoughtful about gender and about what it means to transition, especially for someone like Ortberg, who built a public reputation as a feminist running a women’s website before coming out ... Something That May Shock and Discredit You is not precisely an explanation for everyone who was wondering why the person they first knew as Mallory Ortberg is now Daniel M. Lavery. It is neither apologetic nor self-justifying, and Ortberg remains very clear on the fact that he does not owe an explanation about himself or his gender to anyone ... Instead, this book reads like an exploration — a funny, gentle, thoughtful exploration — of how Ortberg sees the world, and how transitioning affected the lens through which he sees it. Reading it feels like reading the Toast felt in 2013, which is to say it feels like coming into contact with a restless and smart mind of profound and specific hyperfixations. It’s a joy.

... a fusion of old and new Ortberg work. It’s a collection of chapters and fragments, pieces that refuse single identities ... The intensity of emotion and self-centeredness are stripped of their high language, and become vividly queer, utterly recognizable, and essential to the gender mode that Ortberg himself is learning to express throughout this collection ... Ortberg is perhaps closer than any other writer to functioning as the voice of progressive millennials ... Every movement of Ortberg’s writing as he considers gender is hesitant, and his use of upspeak inflection both satirizes the femininity associated with that questioning tone and engages with it genuinely. There must be a space between being prepared to mock gender norms and being deeply uncertain about them. The sincerity beneath the humor is new in Ortberg’s work, and powerful and well as disconcerting ... The book is emotionally effective, but not always entirely accessible. In many ways, Ortberg’s transition is likely to be less alien to many readers than his deep Biblical knowledge ... Ortberg’s least accessible book, but also his most important. Unlike his earlier work, Shock and Discredit must be read slowly, and with reflection. It’s not always easy. The breezy humor sometimes dives deep into New Testament referentiality without actually gesturing to deep faith. Read slowly to keep from flailing. Ortberg’s writing will wait for you to catch up.

The co-founder of The Toast and Slate advice columnist demonstrates his impressive range in this new collection ... In a delightful hybrid of a book—part memoir, part collection of personal essays, part extended riff on pop culture—Ortberg...blends genres with expert facility ... Those long sentences and goofy yet sharp sense of humor thread together Ortberg’s playful takes on pop culture as he explores everything from House Hunters to Golden Girls to Lord Byron, Lacan, and Rilke. But what makes these wide-ranging essays work as a coherent collection are the author’s poignant reflections on faith and gender. Since publishing his last book, Ortberg has come out as trans, and he offers breathtaking accounts of his process of coming to terms with his faith and his evolving relationships with the women in his life ... Throughout, Ortberg’s writing is vulnerable but confident, specific but never narrow, literal and lyrical. The author is refreshingly unafraid of his own uncertainty, but he’s always definitive where it counts ... You’ll laugh, you’ll cry, often both at once. Everyone should read this extraordinary book.

Slate advice columnist Ortberg ...brings the full force of his wit and literary depth to this genre-bending essay collection. Describing it as 'memoir-adjacent,' Ortberg intersperses searingly honest passages about his journey as a transgender man with laugh-out-loud funny literary pastiche ... Ortberg provides an often hilarious, sometimes discomfiting, but invariably honest account of one man’s becoming.