How Not To Be a Boy Summary, PDF, EPUB, Audio

Q: What is *How Not to Be a Boy* about?

*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.

How Not To Be a Boy

Robert Webb

4.18 (15684 Reviews)

Biography

Psychology

Self-growth

Relationship

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FAQs

In "How Not to Be a Boy," comedian Robert Webb hilariously dismantles toxic masculinity while breaking your heart. This Sunday Times bestseller sparked nationwide conversations about gender roles, with critics calling it both "disarming" and "impactful." What happens when boys finally cry?

What is How Not to Be a Boy about?

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.

Who should read How Not to Be a Boy?

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.

Is How Not to Be a Boy worth reading?

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.

How does Robert Webb address masculinity in the book?

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.

Does How Not to Be a Boy offer a feminist perspective?

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.

How does Webb’s comedy career influence the book’s tone?

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.

How does How Not to Be a Boy compare to other memoirs about masculinity?

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.

What critiques exist about How Not to Be a Boy?

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.

Are there iconic quotes from How Not to Be a Boy?

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.

How does the book encourage rethinking gender norms?

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.

What awards or recognition has How Not to Be a Boy received?

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.

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Key takeaways

When Masculinity Becomes a Cage

00:00

A fifteen-year-old boy stares at his bedroom wall, where Van Gogh prints have replaced Star Wars posters. He's plotting how to impress a sixth-former through his end-of-term sketch show, trapped between who he's supposed to be and who he actually is. This isn't just teenage angst-it's the beginning of a lifelong reckoning with what it means to be male in a world that writes the script before you can speak. Growing up means learning the rules, but what happens when those rules are designed to break you? What if the very things we teach boys to become-tough, unemotional, dominant-are the things that destroy their capacity for connection, joy, and wholeness? In a respectable Lincolnshire village, a father looms like a storm cloud. He knocks boys off chairs at dinner. He thrashes his son with his own shorts for no clear reason. He laughs when children fall down stairs because pain is something to be conquered, not felt. This wasn't sadism-it was parenting. In the 1970s, this was what fathers did: worked dangerous jobs, drank heavily, kept order through fear. The man everyone loved at the pub was a different person behind closed doors, and his wife bore the weight of that difference until she couldn't anymore.

Learning Violence as Love

The Performance of Being Male

When the Center Cannot Hold

Comedy as Armor, Success as Substitute

The Reckoning Arrives

Becoming Fully Human

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"Reading used to feel like a chore. Now it’s just part of my lifestyle."

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"BeFreed turned my commute into learning time. 20-min podcasts are perfect for finishing books I never had time for."

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"BeFreed replaced my podcast queue. Imagine Spotify for books — that’s it. 🙌"

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"It is great for me to learn something from the book without reading it."

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@Leo, Law Student, UPenn

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"Instead of endless scrolling, I just hit play on BeFreed. It saves me so much time."

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"I never knew where to start with nonfiction—BeFreed’s book lists turned into podcasts gave me a clear path."

@Chloe, Solo founder, LA

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"Perfect balance between learning and entertainment. Finished ‘Thinking, Fast and Slow’ on my commute this week."

@Raaaaaachelw

"Crazy how much I learned while walking the dog. BeFreed = small habits → big gains."

@Matt, YC alum

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"Reading used to feel like a chore. Now it’s just part of my lifestyle."

@Erin, Investment Banking Associate , NYC

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"Feels effortless compared to reading. I’ve finished 6 books this month already."

@djmikemoore

"BeFreed turned my guilty doomscrolling into something that feels productive and inspiring."

@Pitiful

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"BeFreed turned my commute into learning time. 20-min podcasts are perfect for finishing books I never had time for."

@SofiaP

"BeFreed replaced my podcast queue. Imagine Spotify for books — that’s it. 🙌"

@Jaded_Falcon

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"It is great for me to learn something from the book without reading it."

@OojasSalunke

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@Leo, Law Student, UPenn

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"Makes me feel smarter every time before going to work"

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How Not To Be a Boy by Robert Webb Summary

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