Reasons for Transitioning: Want to impress good-looking ex; Want to upset good-looking ex; Bored of existing wardrobe, looking for excuse to buy all-new clothes that don’t fit in a new way; Younger siblings getting too much attention; Neoliberalism??; Want to sing both parts of a duet at karaoke; Something about upper-body strength; Excited to reinforce a different set of sexist stereotypes; Cheaper haircuts; Just love layering shirts …

From the beloved writer behind The Toast and Slate’s ‘Dear Prudence' column comes a personal essay collection exploring popular culture, literature, religion, and sexuality. With wit and compassion, Daniel Mallory Ortberg revisits beloved cultural and literary figures in the light of his transition.