Daniel Mallory Ortberg

Daniel Mallory Ortberg is “a multifaceted, spinning-top kind of genius,” said

in NYMag.com. Born Mallory Ortberg, the daughter of evangelical Christian pastors, Ortberg won a devoted audience as a humorist and co-founder of The-Toast.net before writing a very funny best-seller and taking over Slate .com’s popular advice column, “Dear Prudence.” Now, at 31, Ortberg is undergoing hormone therapy to change gender while at the same time promoting The Merry Spinster, a new book of strange, brilliant stories based on fairy tales. In one of them, a parent bids farewell to a child who’s fallen in love with a mermaid, and Ortberg admits seeing in the story echoes of the very personal challenge of having to say goodbye to Mallory Ortberg. “She was beautiful, and I loved her,” he says. “And I do—she is not gone, there has been no death, no act of disavowal.”

Not that it’s easy to be touring for the book as Daniel, not Mallory, said in TheRumpus.net. “I have been incredibly excited for a long time, and I would say really anxious,” Ortberg says. “I’m anxious about being seen. I’m anxious with the thought of people saying, ‘You look different.’ I’m anxious at the thought of people saying nothing.” It does help the conversations that many of the book’s stories feature genderrole swapping: Girls are given boys’ names and vice versa. A year ago, those choices would have confidently been read as feminist provocation, and Ortberg admits there have been times it’s felt “painfully ironic” to be a longtime critic of male privilege transitioning to male. On the other hand, as he says, “There’s nothing to be done about that.”