How Not To Be a Boy by Robert Webb Summary

How Not to Be a Boy is a 2017 memoir by British comedian Robert Webb, blending personal anecdotes with critiques of traditional masculinity. It explores Webb’s upbringing, his mother’s death, and societal gender expectations, using humor and vulnerability to challenge toxic norms. The book also reflects on parenthood, grief, and Webb’s journey to unlearn restrictive male stereotypes.

This memoir appeals to readers interested in gender studies, masculinity, and feminist perspectives, as well as fans of Webb’s comedy (Peep Show, Mitchell and Webb). It’s particularly relevant for those navigating identity or seeking insights into breaking free from societal expectations around gender roles.

Yes—critics praised its mix of wit and earnest reflection, earning it a Chortle Award and a spot on The Sunday Times Bestseller List for eight weeks. While more introspective than comedic, its candid exploration of vulnerability resonates with readers reevaluating gender norms.

Webb critiques rigid male stereotypes by recounting his childhood adherence to “boy rules” (e.g., suppressing emotions) and later rejecting them. He argues traditional masculinity harms men by discouraging vulnerability, using his father’s stoicism and his own parenthood as examples.

Webb details his mother’s death from cancer at 17, growing up on a council estate, and his strained relationship with his father. He also discusses attending Cambridge University, joining Footlights, and becoming a parent, linking these events to his evolving views on gender.

Yes. Webb examines how patriarchal norms limit both men and women, advocating for emotional openness and rejecting the “boys don’t cry” mentality. He credits feminism with helping him navigate grief and fatherhood more healthily.

Though tackling serious themes, Webb infuses dry humor and self-deprecation, reminiscent of his work in Peep Show and That Mitchell and Webb Look. This balance makes complex gender discussions accessible without trivializing them.

Unlike academic texts, Webb’s memoir uses autobiographical storytelling to dissect gender roles, similar to Caitlin Moran’s How to Be a Woman. Its blend of humor and raw honesty distinguishes it from more polemical works.

Some readers expected more comedy, given Webb’s background, but found it introspective. Others noted its focus on middle-class British experiences, though its core themes of gender flexibility have broad relevance.

A standout line: “The first lesson of being a man: don’t cry. The second lesson: don’t talk about the first lesson.” Webb uses such aphorisms to underscore the absurdity of male emotional suppression.

By framing his life as a series of “boy rules” to unlearn, Webb challenges readers to question societal expectations. He emphasizes that traits like sensitivity or nurturing aren’t gendered, urging men to embrace full emotional range.

The memoir won a Chortle Award, topped the Sunday Times non-fiction chart, and was serialized in The Guardian. Its audiobook, narrated by Webb, became Audible’s bestselling memoir of 2017.