Daniel Mallory Ortberg isn’t just the cofounder of The Toast and the exceptional advice columnist behind Slate’s “Dear Prudence.” They (Ortberg recently announced their transition) are also an author. Their new book The Merry Spinster is a collection of disconcerting updates on classic children’s stories—stories updated, fractured, re-spun, turned inside out. (We have never felt quite so bad for The Wind in the Willows’ Toad.)
Given the fairy-tale bent of Ortberg’s new book, and their knack for advice that we want to read even when we’ve got nothing in common with the asker, we thought it was time to combine the two. So we collected a few questions from characters you may or may not recognize (all querents retain full anonymity, obviously) and asked Ortberg for their fantastical—and just plain fantastic—advice.
Why hasn’t my Hogwarts letter arrived yet?