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.

What personal experiences does Webb share in *How Not to Be a Boy*?

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.

How Not to Be a Boy

Robert Webb

4.18(15684 Reviews)

Overview of How Not to Be a Boy

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?

Choose how it's told

One book. Many ways to hear it.

Same ideas from How Not to Be a Boy. Pick the voice, depth, and pace that fits you. Switch anytime.

Chapter 1

Breaking the Mold: A Journey Through Boyhood and Beyond

Robert Webb's memoir opens like a time capsule of adolescence-a fifteen-year-old boy in a small bedroom with damp walls, Van Gogh prints replacing Star Wars posters, plotting to impress sixth-former Tess Rampling through his end-of-term sketch show. This is a story that resonates deeply with anyone who's ever felt trapped by gender expectations. Since its 2017 publication, the book has become a cultural touchstone, praised by figures from Emma Watson to Stephen Fry for its unflinching examination of masculinity. Webb, best known for his work in the BAFTA-winning comedy "Peep Show," crafts a narrative that's both deeply personal and universally relevant, using his own experiences to illuminate the often-invisible prison of gender norms that shapes boys into men-often at great cost to themselves and others.

Chapter 2

The Shadow of a Father

Growing up in Woodhall Spa, Lincolnshire-a respectable, conservative village that young Robert initially thought was the most normal place in England-his father Paul loomed like Darth Vader. Constantly wasted and prone to violent outbursts, he'd knock Robert's older brothers off chairs for minor infractions at dinner and once thrashed Robert with his own shorts for no clear reason. Though there were occasional happy moments, especially when he was out, life with him was like a bad dream. Paul wasn't a sadist. He laughed when Robert fell down stairs because he was trying to teach him to treat pain lightly. Poor old Dad with his three small boys, insufficiently compliant wife, dangerous job, and drink problem (which by 1970s standards was no problem at all). He was doing what men were supposed to do-working hard, drinking heavily, keeping his boys in line. But he couldn't quite keep his wife in line. In 1992, aged nineteen and living with Dad again, Robert met a man in a pub who told him about Dad's legendary reputation for "drinking, fucking and fighting" in the seventies. He felt strangely proud, looking for connection with his living parent. But as he wobbled home, he wondered if this would really be the bonding experience he sought. The childhood drawing of their house was incomplete. Someone was missing-Martin John Webb, Robert's eldest brother, who died of meningitis when he was six. His brother died and Robert was born ten months later. When terrible things happen, people encourage us to talk about our feelings. But boys are specifically trained not to do this. When we tell boys to "man up," we're saying "stop expressing those feelings"-or worse, "stop feeling those feelings." Men express anger when what they're actually feeling is shame, fear, uncertainty, anxiety, or grief. Dad's public face was beloved by the entire village-generous, charismatic, kind. They adored him. But they didn't have to live with him. Mum did, until she couldn't anymore.

See every word as you hear it

Read along effortlessly as each word of How Not to Be a Boy lights up in real time.

Chapter 3

The Rules of Boyhood

At seven years old, Robert understood the "Sovereign Importance of Early Homophobia" and the "Paramount Objective of Despising Girls"-playing with girls was considered lunacy. This gendered play wasn't innate but learned. In leafy den hideouts around the golf club grounds where his grandfather worked, he'd retreat to plan adventures while contemplating the approaching school year and listening to Phantom jets overhead. In his imaginary world, he led the Guy-Buys, twelve men who fought crime. They weren't disciples or boyfriends but bodyguards-protection from a world where attention hurts. At Coningsby Infant School, he was the quiet one, earning compliments from mothers at birthday parties while feeling uneasy because boys weren't supposed to be quiet but "cheeky" like his brothers. Boys would stride around the playground chanting "All join up for playing... War. NO GIRLS!" Girls were ruthlessly excluded, and they'd destroy anything they built, like snowmen. The culture and language made despising girls effortless, especially for someone frightened and insecure like Robert. Two years earlier, when meeting his new teacher Mrs. Walker, he'd become "Mutey McMute-Child" while his embarrassed mum explained he was "shy"-a kinder explanation than admitting he was traumatized by domestic violence and haunted by nightmares of his father. At the Golf Club, he once found a dying bumblebee and built a stone circle to protect it, crying secretly because he knew boys were supposed to stamp on bees, not save them. At nine years old, sitting on the school wall with his friend Roger Baxter, Robert was mortified by his socks. It was Sports Day, and the new rule required white socks, but Auntie Tru had bought him what were unmistakably girls' socks-long, patterned, and full of holes. He picked his nose in distress, wondering how she could do this to him. In the playground, he tried running fast enough that his legs became a blur, hoping no one would notice his rolled-down socks bulging "like Day-Glo bagels." But it was too late-the other boys spotted them. Matthew Tellis started taunting: "Look at Robert! Good socks, Robert! Ha-ha! My name's Robert and I'm a girl!" As boys circled threateningly, Roger defended him: "Shurrup, Tellis, y'wassock, it's not his fault, it's his auntie!" Emboldened by Roger's support, Robert counter-attacked by referencing an infamous incident where Tellis had an accident in class: "Maybe they'd look better if my legs were covered in shit, Matthew." The boys erupted in laughter. There's a fragile honor among schoolboys about certain topics-unless one is cornered and called a girl. Then all bets are off.

Chapter 4

The Pressure to Be Brave

Junior school brought the alarming novelty of male teachers, including Headmaster Mr. Morgan, a stern, bald man with glasses who welcomed new students before stiffening when discussing "Rules... to be obeyed!" Corporal punishment still existed in 1980, with rumors that Mr. Morgan used a slipper. Another teacher, Mr. Duke, kept a yellow wooden stick nicknamed "The Yellow Peril" on his desk. Though seemingly amiable with his jokes, Robert feared he might suddenly "come at me with a fucking stick." Robert's relationship with his brothers was complex. Mark, the eldest surviving brother, was his idol-The King, The Fonz, Tucker Jenkins, and Han Solo rolled into one. Dark with brown eyes like Mom, rather than pale and fair like Robert, Andrew and Dad, Mark seemed to embody everything a boy was supposed to be. Yet when asked to describe Robert in one word for a BBC documentary years later, Mark immediately said "Spoilt"-a familiar refrain from Robert's youth alongside "Robert is shy." The evidence was clear: Nan and Trudy cut crusts off his sandwiches, skinned his sausages, and removed pips from grapes. While his teenage brothers shared a bedroom, he had his own. He enjoyed special trips to Lincoln with Nan, John and Tru, visiting the Cash & Carry, bookshops for Doctor Who paperbacks, and the glamorous Berni Inn for rump steak. Mom indulged him most significantly by reading him bedtime stories between ages five and seven-something she never had time for with his brothers. The Lion, the Witch and the Wardrobe, The Jungle Book, and his favorite, The Adventures of Tom Sawyer (which she read with a Southern accent). Robert acknowledges his privilege as an able-bodied white male without serious illness, now educated, middle-class and well-paid. But he recognizes this isn't achievement-it's luck. Privilege is just a posh word for luck. He thinks about Martin, whose death enabled his birth. Sometimes as a drunk teen, he'd look at the Lincolnshire night sky and thank him, though he never knew him and Martin never intended to die. His greatest strokes of fortune were having a family who loved him and someone who inspired him to read-not because reading makes you smart, but because stories let you imagine being someone else, something boys aren't much encouraged to do.

Get more out of How Not to Be a Boy

Get daily insights from 100K+ lessons
Words light up in sync with the audio
Your library saved on every device

Chapter 5

Grammar School and Growing Pains

At Grammar School, Robert noticed half the children spoke differently-pronouncing "fast" to rhyme with "farce" and calling bedrooms "bed-ruhms." They placed their cutlery at angles after meals and had exotic experiences like visiting Tuscany or owning pianos. They were always first with their hands up, and though not always the smartest, they became smarter through talking. The teasing of "Clever Boys" reflected a wider ambivalence about boys and education. Throughout primary school, they were aware of stereotypes that boys can't sit still, are disruptive, have "too much testosterone" to concentrate, and prefer footballs to books. These beliefs likely affected boys' academic performance, with many living down to these expectations. Even at QEGS, where they were told they were "super-duper and tremendously lucky," gender expectations persisted. A top-performing girl must attribute her success to hard work, while a boy must claim it was done last-minute with natural talent. It was acceptable only if you didn't make an effort-being a "girlie swot" was forbidden. Friday nights brought loud arguments between Mark and Andrew as they prepared for evenings of "sex and violence" at Coningsby Community Centre. Their bathroom disputes played out to either Status Quo or Sex Pistols, depending on who won the music selection battle. Their exchanges were filled with homophobic insults and threats, though Andrew found humor in provoking Mark despite knowing it would end in a "slap." The only time Andrew spoke positively about Mark was when describing how Mark let a woman beat him up without fighting back or even protecting himself-standing with hands behind his back in a display of contempt that required remarkable physical courage. Their hostile relationship continued for thirty years, influenced by a violent father, an absent father, and masculine insistence on competition. "Some men don't recover from masculinity at all," Robert observes, questioning what masculinity even is beyond stereotypes about driving gloves and body odor.

Chapter 6

Finding a Voice

In 1986, at thirteen, Robert's confidence began to grow when Mrs. Slater asked him to take over the main part in their class play for the Eisteddfod after Pete Garvey fell ill with appendicitis. Despite his previous terror of acting-having only delivered one line as King Herod's Captain in a school nativity-he'd been enjoying playing the chauffeur Webb, a Jeeves-like character. He discovered he had an innate sense of comic timing, learning to make the audience wait for his "Indeed, sir" lines. Form 2S won the Eisteddfod, and his Basil Fawlty-inspired performance was a hit. Afterward, people looked at him differently-a look he could get used to. That night, watching Martin Clunes in a BBC sitcom, he realized his overwhelming desire was to be famous-famous people seemed safe, problem-free, and admired. He decided then that funny writing and acting would be his path to fame, just as puberty was beginning its chaotic arrival. His first dance came at Cathy Shepherd's thirteenth birthday party at her father's pub. Before dancing, they played Spin the Bottle, which he found simultaneously boring and mortifying. The only girl he wanted to kiss was Tiffany Rampling, who sat aloof with her friend Zelda, refusing to play such an "immature game." Later, Cathy's supervising older sister Chrissy arranged for him to slow dance with the birthday girl. Neither of them had danced before, so Chrissy positioned his hands on Cathy's waist and hers around his neck. They awkwardly swayed through "Feed the World" by Band Aid-a poor choice for romantic dancing given its theme of starving children. During a visit to his great-aunt Dot after Nan's funeral, he declined joining her and Trudy for Bingo, though he'd previously enjoyed it. He felt he was supposed to act "too old" for such activities-not because he didn't want to go, but because he sensed it was expected of teenage boys. It wasn't so much "Act Your Age" as "Act Your Gender"-as if boys could muddle through childhood, but teenage boys had to turn professional. Here's a more TTS-suitable version that preserves the core narrative and emotional depth while using more appropriate language:

See every word as you hear it

Read along effortlessly as each word of How Not to Be a Boy lights up in real time.

Chapter 7

Complicated Friendships

Robert and his childhood friend Roger's relationship fractured over musical preferences. Their friendship had grown uniquely close, though neither could express their deep platonic bond. As teenagers, they struggled with traditional expectations about male friendship. Their connection had been strong enough to make ceremonial promises of brotherhood three years prior, but now they were drifting apart. The catalyst came when Robert criticized the popular group Bros. Long-simmering tensions over social dynamics emerged when Robert dismissed their hit song with harsh criticism. Roger challenged him to suggest better music, leading to a debate about "Ideal World" by The Christians. Robert's true feelings stemmed from adolescent insecurity - he felt overshadowed by the band's popularity among their peers. At fifteen, he was increasingly self-conscious about his social development. Will became Robert's new closest friend. Robert appreciated Will's confidence and admired his natural style - from his effortlessly trendy hairstyles to his fashion choices. Will had an innate ability to anticipate trends, whether it was abandoning digital watches, experimenting with different hairstyles, or choosing sophisticated fragrances. His clothing choices were always impeccable, moving with natural grace. Their friendship deepened when they shared a GCSE Media Studies class, collaborating on a documentary about social stereotypes. Robert took on creative leadership, drawing from his experience writing school performances where Will played the straight-faced interviewer. Robert found himself captivated by Will's genuine reactions to his humor. Robert's sixteenth birthday was spent working at Gateway supermarket, earning modest wages but taking pride in mastering the price gun nearly as well as his experienced colleague Tony. Some older students presented him with an embarrassing but well-intentioned gift, leading to an awkward moment where he tried to maintain composure but couldn't hide his discomfort.

Chapter 8

Facing Loss

Dad delivered the news of Mum's terminal cancer with startling bluntness: "Y'mum's poorly, boy. It's terminal." Instead of emotional support, he immediately pivoted to practical matters like cleaning arrangements, while Derek (Robert's stepfather) worried about cleaner costs. Their emotional detachment stood in stark contrast to Robert's tears. Dad gave him an awkward hug before leaving for the pub, his van ironically emblazoned "Paul Webb, Ltd." Later, Robert sat with Mum watching Dallas. She apologized for Dad's tactless revelation and asked if he had anything to ask her. Instead of profound questions, he confessed his virginity, embarrassed by pretending otherwise. She reassured him: "You'll overtake them. In everything." When he promised to get three As and attend Cambridge, she responded, "I'm proud of you already." She told him this was still his home, regardless of Dad's suggestions. In a poignant moment, she connected his birth to the death of his brother Martin: "You came along soon after Martin died and I think that's why we've always been close." As she weakened, he suggested maybe she'd see Martin again, and she replied, "I 'ope so." As Mum deteriorated, her friend Carole demonstrated "the point and meaning of friendship" by taking charge with practical compassion, while a parade of awkward well-wishers forced Mum into the exhausting role of host despite her condition. Robert's diary entries became increasingly sparse and desperate: "April 17th: Mum's condition deteriorates. I felt so alone, so pathetic today." "April 23rd: Dr Campbell says 24 hours at the most." The final entry simply stated: "April 24th: Mum dies at 2.45 p.m. I love you." Mark told him "She's gone" as he entered the bedroom to find Mum's body-present but absent. He struggled with the finality, unable to accept he'd never hear her voice or feel her embrace again. In the garden with Mark, they attempted stoicism, trying not to cry for each other's sake. When three-year-old Anna-Beth asked where her mother was, Nan Webb didn't hesitate: "With Jesus!" Robert desperately wanted to believe this comforting fiction. His grief quickly transformed into a messianic self-narrative-he'd become his mother's voice, stronger and male-advantaged. His heart froze as a protective measure while his mind constructed this grandiose coping mechanism.

Get more out of How Not to Be a Boy

Get daily insights from 100K+ lessons
Words light up in sync with the audio
Your library saved on every device

Chapter 9

The Path to Cambridge

Mark drove Robert directly from the funeral to school, where he was due to join a university fair trip. He sewed his school badge back onto his blazer in the car, having used his uniform for the funeral. At school, he found a strange satisfaction in how his friends made space for him, in how he could demonstrate brave coping to his peers. At the fair, he approached the Cambridge representative sitting alone-a grey-haired woman named Catherine from King's College. Despite his awkwardness and doubts about his academic record, she encouraged him gently. When he accidentally mentioned his mother's funeral was that very morning, her compassion nearly broke him. "You're sitting in the right chair," she assured him, "It's not stupid in the slightest for you to think of us." She gave his hand a squeeze before he left with a prospectus, wondering why she had to make such a fuss about the funeral. Shortly after the funeral, he began dating Isabel, who'd recently broken up with "hairy Edmund." For once, this girl actually fancied him back. After weeks of flirting, they spent a Sunday afternoon together that ended with them going upstairs at her parents' house and later to his, where they had sex. Despite his previous dramatic anguish about virginity, his diary entry about losing it was remarkably restrained. The relationship lasted about six months, during which he treated her poorly-ignoring her at school, criticizing her friends, and failing to show interest in her life. He couldn't bring himself to dump her, so he behaved badly until she did it for him, culminating in his absence from her eighteenth birthday. The truth was, compared to his intense infatuations with others, Isabel was merely someone he held "in really quite high esteem"-she was real, and reality wasn't his thing. His cruelty to Isabel stemmed partly from profound unhappiness. Mum's absence felt like a daily assault-he'd dream of her all night and wake to emotional pain. Her absence was more like a presence, as inescapable as a black hole. Meanwhile, Derek struggled to raise three-year-old Anna-Beth with zero experience, and the pressure of A-levels with his self-imposed fantasy of escape through academic success became overwhelming.

Chapter 10

Finding His Way

Robert broke the news to Derek that he was moving out to live with his father. Derek made it harder by saying all the wrong things, like "y'poor old mum wanted you to stay here with us." Robert felt terrible about abandoning Anna-Beth, but was determined to move for his exam retakes. When Derek asked if it was something he'd done wrong, Robert lied and said he just needed a change of scene, though they both knew it was more complicated than that. Dad established "just a few guidelines" for their living arrangement. Robert was to do the washing-up, including thoroughly cleaning milk bottles. The items in the front room must remain at perfect right angles. His bedroom curtains must be open by 8 a.m. so neighbors don't think he's a layabout. His car must be parked in an exact spot to avoid making "the place look untidy." He taught Robert poorly how to use the washing machine and reminded him to use the toilet brush properly, especially when Delia stayed, because "you know what women are like." Despite his efforts to get into Cambridge specifically for Footlights, they rejected him from all three main shows during his first year. He watched their performances with bitter contempt, convinced they'd overlooked his "talent" that he wore like armor. Everything changed in his second year when they put him in everything. After doing well in comedy nights called Smokers, he caught the Committee's attention. The outgoing president Miles Williams called to tell him he was funny with "bags of talent" and should be in all three shows next year. When he finally performed in these shows, he felt like "the benevolent king of their joy," recognized in the streets of Cambridge. Meanwhile, his academics suffered catastrophically. Having neglected the mandatory Old English language component for a year, he faced Cambridge's demanding one-on-one tutorials completely unprepared. The Robinson College Education Committee summoned him for what became a terrifying interrogation about his academic performance. Desperate, he deployed emotional manipulation-letting tears form while confessing about falling in love with a boy, having a casual relationship with a girl named Lily, and how they started dating each other, connecting it all to his mother's death. The performance worked; instead of expulsion, they agreed to a work schedule. He barely passed with a 2:2.

See every word as you hear it

Read along effortlessly as each word of How Not to Be a Boy lights up in real time.

Chapter 11

Relationships and Revelations

After falling for Clara, Robert was convinced their future was set. When Simon Shingles booked the Brighton Dome for their Footlights show during the 1994 World Cup Final, they discovered only twelve tickets had sold. Instead of flyering, Robert escaped to Brighton's nudist beach where he was approached by Bryan, a sixty-year-old man whose unwanted attention taught him a limited lesson about sexual harassment-though he later realized he'd learned almost nothing about women's experiences with harassment since he never faced the physical power imbalance women do. Clara visited his family in Woodhall Spa where he dreamed about their future together while swinging in the park. But their relationship struggled when she began a miserable director's course in London. As she grew unhappy, he became increasingly insufferable at Cambridge, where he was now Footlights vice-president, writing the pantomime "Dick Wittington" with Charlie. They were both at the "zenith of arrogant, insecure, minty dreadfulness," showing up late to meetings, making tosspot pronouncements, and generally amusing some while infuriating others. Clara arrived at Robinson College and delivered the news: she'd had a fling with "Tony the Techie" and was ending their relationship-or as she put it, "we don't really have a relationship." Rather than getting angry, Robert announced he'd need to return to counseling, implying she'd made his important pantomime job difficult. Despite his passive-aggressive response, she stayed to watch the show. Just eight days after Clara dumped him, he met Jenna at the panto cast party. They ran giggling through the streets, snogging all the way to her house, and began a relationship that lasted eight years. Yet he made things difficult for "Little Lord Rebound," keeping Clara's poster on his wall for months and never quite providing the romance Jenna deserved. Their Valentine's Day was spent writing silly cast biographies, they split restaurant bills, and their happiest day was discovering she wasn't pregnant after a condom malfunction.

Chapter 12

Breaking the Cycle

In 2015, Robert's five-year-old daughter Esme asked her mother Abigail if she'd be laughed at for dressing as Spider-Man instead of a princess on non-uniform day. They'd taught their daughters about "The Trick"-their family code for gender expectations that harm both girls and boys. Feminism isn't about men versus women; it's about men and women versus The Trick. Robert met Abbie in 2003 recording a Radio 4 comedy show called Concrete Cow. With Peep Show about to air, he affected humility while secretly feeling important. Abbie saw right through him, mocking his story about being "one of the main ones." Her flirtation technique was equally immature-singing a made-up song called "Pretty boy is a fucking moron" when he claimed Shakespeare's comedies weren't funny. They gradually lost the rest of the cast after dinner, snogged in a taxi, and three weeks later he confessed his love in a Clapham pub. She replied, "My heart is full." Three years later, they married at St. Paul's Church in Covent Garden, surrounded by friends and family, exchanging "absurdly, magnificently far-fetched vows." Despite his beliefs in equality, he fell into the same paternal patterns he'd witnessed growing up. He promised Abbie a 50/50 partnership in housework and childcare, but instead said yes to every job opportunity in breadwinning panic-from forgettable TV shows like "Great Movie Mistakes" to voice-overs. When not working, he'd drink outside, smoking and fantasizing about violence. Twitter became his virtual pub, where he'd pick pointless fights before staggering home at 3am to an increasingly frustrated wife. Eventually Abbie wrote him a letter saying how much she missed him. In 2012, he visited his ninety-year-old grandfather John ("Dada") in his care home with Abbie and their daughters Esme (three) and baby Dory. When Abbie took Dory for a buggy ride, he read Julia Donaldson's "Zog" to Esme while John listened. When Esme asked if dragons are real, he told her no, and she wisely responded, "But they're real in the story." John mentioned wishing he'd read more stories to Robert's mother Pat, triggering reflections on how life's tragedies connect to its joys. Robert had spent years constructing a narrative where his mother's death led to everything good in his life-meeting David Mitchell, creating their comedy partnership, meeting Abbie, having his daughters. But Abbie found this thinking insane, and her talking him out of it helped him become a better husband and father. He had to face that he's "just this... bloke"-one who avoided being a "proper man" yet took his wife for granted. He hid behind being the sensitive man who wrote anti-sexist comedy, while failing to be an equal partner at home. The deaths of John, Derek, and Dad forced him to abandon his "provisional" mindset. He doesn't want a "Mature Masculinity" with capital letters-we've seen enough failed stereotypes from the "New Man" to the "New Lad." He wants everyone to express their individual selves with confidence and humility, free from restrictive gender conditioning. For his daughters' sake, he's learning to take responsibility-from laundry to emotional regulation-so they'll expect good things from men. The gender "Trick" wastes everyone's time, creating barriers between all relationships. Those of us who are loved have no excuse not to be fully human, compassionate, and committed to friendship and love.

★★★★★

You made it to the end of How Not to Be a Boy

Loved by 1M+ learners

“23 days in and I have used it every single day. It is part of my daily habit now.”

jayallen

Key Themes in How Not to Be a Boy

toxic masculinity
gender socialization
repressed emotion
father son conflict
childhood trauma

Quotes from How Not to Be a Boy

When we tell boys to "man up," we're saying "stop expressing those feelings."
Attention hurts.
Boys would stride around the playground chanting "All join up for playing... War. NO GIRLS!"
He was doing what men were supposed to do-working hard, drinking heavily, keeping his boys in line.

Characters in How Not to Be a Boy

Robert WebbThe author and protagonist of the memoir
Paul WebbRobert's father, a charismatic but violent man
Pat WebbRobert's mother who endured domestic violence
Roger BaxterRobert's childhood friend who defended him
Matthew TellisA school peer who taunted Robert for his socks

About the Author

Robert Patrick Webb, award-winning British comedian and bestselling author of How Not to Be a Boy, explores themes of masculinity, gender roles, and feminism through his deeply personal memoir.

Born in 1972 in Lincolnshire, Webb draws on his working-class upbringing, his mother’s early death, and his experiences as a father to challenge traditional notions of manhood.

A Cambridge English graduate and one-half of the iconic comedy duo Mitchell and Webb, he co-created BAFTA-winning shows like Peep Show and That Mitchell and Webb Look. Webb’s debut novel, Come Again, continues his examination of identity and relationships.

A 2023 Booker Prize judge, Webb has contributed to The Guardian, New Statesman, and BBC Radio 4’s Book of the Week. How Not to Be a Boy topped The Sunday Times bestseller list for eight weeks, won a Chortle Award, and became Audible’s bestselling memoir of 2017, narrated by Webb himself.

Download Summary of How Not to Be a Boy

Get the How Not to Be a Boy summary as a free PDF or EPUB. Print it or read offline anytime.

Users also liked

Of Boys and Men

Richard Reeves

James O'Brien

Caitlin Moran

Peggy Orenstein

Dan Kindlon

Robert A. Glover

Garrard Conley

FAQs About This Book

Discover more

LEARNING PLAN

Nurture sons for lifelong well-being

Raising boys in the modern world requires a specialized approach to emotional development and character building. This plan is essential for parents and mentors seeking to bridge the communication gap and foster authentic masculinity from childhood through adulthood.

4 h 50 m•4 Sections

LEARNING PLAN

The Way of the Superior Man

This plan is essential for men seeking to integrate their spiritual purpose with their intimate relationships. It provides a roadmap for those who want to master their emotions and energy while leading with authenticity and strength.

2 h 15 m•4 Sections

LEARNING PLAN

Best books to learn how to flirt

Navigating the complexities of modern dating requires a blend of psychological insight and refined social skills. This guide is designed for anyone looking to overcome social anxiety and build authentic romantic connections through proven communication techniques.

4 h 16 m•4 Sections

LEARNING PLAN

How to not care what others think of you.

This learning plan is essential for anyone struggling with social anxiety, chronic people-pleasing, or a loud inner critic. It provides a roadmap for individuals seeking to reclaim their autonomy and build a life rooted in authentic self-worth rather than external validation.

4 h 22 m•4 Sections

LEARNING PLAN

The Only-Child's Guide to Self-Reliance

This guide is essential for individuals who grew up as only children and find themselves struggling with social integration or decision paralysis. It provides a roadmap for transforming solo-oriented habits into collaborative strengths and self-assured leadership.

1 h 12 m•3 Sections

LEARNING PLAN

The Radical Self-Worth Blueprint

This blueprint is essential for high-achievers who struggle with chronic self-criticism and burnout. It provides a structured path to decouple identity from output, benefiting anyone seeking a more resilient and compassionate relationship with themselves.

1 h 12 m•3 Sections

LEARNING PLAN

The Courage to Be You

In a world driven by social media and constant comparison, many people struggle with the biological urge to people-please at the expense of their own identity. This plan is designed for professionals and individuals who feel held back by social anxiety or the need for external approval. It offers a psychological roadmap to reclaiming your voice and living with integrity.

1 h 12 m•3 Sections

LEARNING PLAN

The Engaged Father's Playbook

Modern fathers often struggle to balance executive pressures with meaningful family engagement. This playbook is designed for high-achieving professionals seeking to master co-parenting and adolescent development without sacrificing career success.

1 h 24 m•4 Sections

From Columbia University alumni built in San Francisco

LOVED BY

1,000,000+ curious minds.

4.7

avg rating

1M+ learners

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

@Moemenn

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

@Chloe, Solo founder, LA

117

"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

108

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

@Erin, Investment Banking Associate , NYC

254

"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

4.5K

"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

201

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

@OojasSalunke

"The themed book list podcasts help me connect ideas across authors—like a guided audio journey."

@Leo, Law Student, UPenn

483

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

@Cashflowbubu

See more on how BeFreed is discussed

From Columbia University alumni built in San Francisco

LOVED BY

1,000,000+ curious minds.

4.7

avg rating

1M+ learners

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

@Moemenn

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

@Chloe, Solo founder, LA

117

"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

108

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

@Erin, Investment Banking Associate , NYC

254

"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

4.5K

"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

201

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

@OojasSalunke

"The themed book list podcasts help me connect ideas across authors—like a guided audio journey."

@Leo, Law Student, UPenn

483

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

@Cashflowbubu

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

@Moemenn

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

@Chloe, Solo founder, LA

117

"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

108

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

@Erin, Investment Banking Associate , NYC

254

"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

4.5K

"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

201

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

@OojasSalunke

"The themed book list podcasts help me connect ideas across authors—like a guided audio journey."

@Leo, Law Student, UPenn

483

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

@Cashflowbubu

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

@Moemenn

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

@Chloe, Solo founder, LA

117

"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

108

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

@Erin, Investment Banking Associate , NYC

254

"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

4.5K

"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

201

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

@OojasSalunke

"The themed book list podcasts help me connect ideas across authors—like a guided audio journey."

@Leo, Law Student, UPenn

483

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

@Cashflowbubu

See more on how BeFreed is discussed

Start your learning journey, now

Chapter 12

How Not to Be a Boy

OverviewOverview of How Not to Be a Boy

One book. Many ways to hear it.

Breaking the Mold: A Journey Through Boyhood and Beyond

The Shadow of a Father

See every word as you hear it

The Rules of Boyhood

The Pressure to Be Brave

Get more out of How Not to Be a Boy

Grammar School and Growing Pains

Finding a Voice

See every word as you hear it

Complicated Friendships

Facing Loss

Get more out of How Not to Be a Boy

The Path to Cambridge

Finding His Way

See every word as you hear it

Relationships and Revelations

Breaking the Cycle

You made it to the end of How Not to Be a Boy

Key Themes in How Not to Be a Boy

Quotes from How Not to Be a Boy

Characters in How Not to Be a Boy

About the Author

Download Summary of How Not to Be a Boy

Users also liked

FAQs About This Book

What is How Not to Be a Boy about?

Who should read How Not to Be a Boy?

Is How Not to Be a Boy worth reading?

How does Robert Webb address masculinity in the book?

Discover more

1,000,000+ curious minds.

1,000,000+ curious minds.

One book. Many ways to hear it.

Breaking the Mold: A Journey Through Boyhood and Beyond

The Shadow of a Father

See every word as you hear it

The Rules of Boyhood

The Pressure to Be Brave

Get more out of How Not to Be a Boy

Grammar School and Growing Pains

Finding a Voice

See every word as you hear it

Complicated Friendships

Facing Loss

Get more out of How Not to Be a Boy

The Path to Cambridge

Finding His Way

See every word as you hear it

Relationships and Revelations

Breaking the Cycle

You made it to the end of How Not to Be a Boy

Users also liked

Discover more

Overview of How Not to Be a Boy