Although Daniel Mallory Ortberg has been the voice and pen behind Slate’s “Dear Prudence” column since late 2015, Ortberg’s new book will be more familiar to fans of The Toast, a feminist satire website he co-founded. Within the pages of this book you will find an episode of House Hunters that wouldn’t be out of place in The Twilight Zone, several Christian parables, and an extremely close reading of William Shatner’s cameo on Columbo. The true heart of this book, though, is Ortberg’s thoughts on transition and his own complicated relationship to masculinity, rounding out this funny, sad, and at times revelatory book.