How Not to Be a Boy is a 2017 memoir by the British comedian Robert Webb. He writes about his childhood, parenthood and other life events, using the experiences to discuss masculinity, gender roles and feminist topics. Major life events include his mother's death from cancer, his attendance at the University of Cambridge and the births of his two daughters. The book arose after Webb wrote a New Statesman article of the same name, and was part of a two-book deal with Canongate Books, the second book being Come Again (2020). How Not to Be a Boy was listed on The Sunday Times's Bestseller List for eight weeks and received a Chortle Award and positive critical reception. Reviewers found the book more serious than comedic and praised its messaging.