How Not to Be a Boy

Robert Webb's memoir examines how rigid expectations of masculinity shaped his life, from a childhood marked by a volatile father and a fiercely loving mother through his unlikely path to Cambridge University and a career in comedy. The book moves chronologically but includes reflective passages, imagined dialogues between Webb at different ages, and direct arguments about gender conditioning.

The overture establishes the book's central tensions through two performances separated by 22 years. In 1987, 15-year-old Webb prepared a mocking lip-sync of Rick Astley for a school sketch show in Coningsby, Lincolnshire, hoping to impress Tess Rampling, a girl two years above him. In 2009, he performed the audition scene from Flashdance on Let's Dance for Comic Relief before seven million viewers. Afterward, his father Paul left a voicemail, voice cracking, saying he was proud and apologizing for not being "much of a family man." Webb did not call him back. That night, he sat alone drinking and smoking while his pregnant wife Abbie slept inside, establishing a pattern she would eventually confront. Webb frames the book as an attempt to understand why he spent 25 years trying to be the opposite of his father, an "abrasive northern male" who "takes women for granted and drinks too much," and why that oppositional project was doomed.

Webb grew up in Woodhall Spa, Lincolnshire, with his mother Pat, his father Paul, a woodsman, and two older brothers, Mark and Andrew. Paul drank heavily and had violent outbursts, sometimes striking the boys. Webb's earliest memory is of falling down the stairs at age two: His mother scooped him up; his father laughed. Before Webb finished his first year of school, Pat divorced Paul. Webb reveals that his eldest brother Martin died of meningitis at age six, and Webb was born 10 months later, a fact he describes as his parents' "reply" to death with remaining love.

Pat remarried Derek Limb, a mild, teetotal man, and they moved to a bungalow in Coningsby. Webb effectively grew up at the Woodhall Spa Golf Club, where his maternal grandparents John and Grace and great-aunt Trudy worked. A solitary child labeled "shy," a word Webb argues masked mild trauma from domestic violence, he invented the Guy-Buys, an imaginary gang of bodyguards, and roamed the Club grounds alone. He already understood two unspoken rules of boyhood: Never play with girls, and never do anything that could be called "gay." One day, finding a dying bumblebee on the gravel, he built a circle of stones around it for protection and cried. He knew what was expected: He was supposed to stamp on it.

Webb's mother read him bedtime stories, instilling a love of reading that he argues taught him empathy. At age 11, told he was academically "borderline," he chose to struggle at the grammar school rather than attend the local secondary modern. At Queen Elizabeth's Grammar School, he was hopeless at sports and intimidated by male teachers, but he found a transformative mentor in English teacher Mrs Slater (Heather), whose delight in language inspired him. When a classmate's illness created an opening in a school drama competition, Slater asked Webb to take the lead. He discovered a gift for comic timing and realized that night he wanted to be famous. He connected fame with safety: Famous children do not get hit or ignored by their fathers.

Webb fell in love with his best friend Will, describing him with barely concealed infatuation while insisting he "just likes his attitude." His feelings produced shame rooted in what Webb calls "the Sovereign Importance of Early Homophobia." He began keeping a diary, reading literature analytically, and asked Slater whether applying to Cambridge was ridiculous. She told him it was not.

At 17, Webb's world collapsed. In March 1990, he learned his mother had terminal lung cancer with approximately four months to live. His father arrived at the bungalow drunk and delivered the news bluntly. In the following weeks, Webb sat with Pat on her bed. She asked if there was anything he wanted to say; he confessed he was a virgin. She told him he would "catch up" and "overtake them. In everything." He promised three As and Cambridge. Pat died on April 24, 1990. Webb found her leftover painkillers in the kitchen and wrote a suicide note but could not go through with it because of what it would do to his family.

On holiday in Torquay, Webb broke down when a Prince song triggered his grief, and Will held his hand in the dark. Slater read Wordsworth's "Tintern Abbey" with him, and the poem helped him begin to heal. His first A-level results, an A in English but two Cs, fell short of Cambridge's requirements. He moved into the family's old house with his father to retake his exams, leaving behind his three-year-old half-sister Anna-Beth. Living with Paul was fraught, but his father showed surprising insight when Webb confessed he had done no work: "Y'mum just died, mate. Might as well have been yesterday." Webb finally studied, earned two As, and was accepted at Robinson College, Cambridge. Paul and Mark drove him there, and Webb felt safer than he had since his mother died.

At Cambridge, Webb poured his energy into Footlights, the university's comedy club, rather than his English degree. He began weekly counseling and watched first-year David Mitchell perform, recognizing a kindred talent and deciding to recruit Mitchell as a comedy partner. Webb fell in love with Clara, a recent Robinson graduate, but the relationship collapsed when she moved to London. He began dating Jenna, a kind fellow student, on the rebound; they stayed together for eight years. Webb graduated with a 2:2, a middling degree. At the ceremony, Paul told him: "I know you'd rather your mum was here, son, but for what it's worth I'm very proud of you."

After Cambridge, Webb and Mitchell shared a London flat, writing comedy while working odd jobs. In 1997, agent Michele Milburn signed them, launching their careers. Webb neglected Jenna, and when he belatedly decided to propose, she broke down and left, saying she had waited years and no longer wanted it. Writers Sam Bain and Jesse Armstrong brought Webb and Mitchell a concept for a sitcom shot from two flatmates' points of view, which became Peep Show on Channel 4.

Webb met Abigail Burdess in 2003 and married her in 2006. He recounts that in 1994, he told his father he had had relationships with both men and women; Paul banged the table with delight, framing it as evidence of typical Webb virility. After the births of daughters Esme and Dory, Webb broke his promise to be an equal partner. He said yes to every job, and when not working, sat outside drinking and smoking. He became, by his own account, "a boring, drunken dick." Abbie wrote him a letter saying how much she missed him. Webb realized that despite a lifetime of trying not to be his father, he had replicated Paul's pattern: an absent, hard-drinking man who took his wife for granted. Abbie told him plainly: "You are not about to amaze everyone by jumping on your horse like Prince Hal." Webb stopped drinking alone, quit smoking, and began doing his share of domestic work.

In Webb's early forties, John, Derek, and Paul all died within a two-year period. None spent their final conversations wishing they had been tougher; they wished they had been more present for the people they loved. Webb delivered his father's eulogy, telling the congregation: "The sadness that we feel now, we can afford to hold close; safe as we are in the knowledge that grief is love's echo." The book closes with Webb playing football in the garden with Esme and Dory. He introduces "The Trick," his family's term for the system of expectations that tells boys to suppress their feelings and girls to limit their ambitions, and reflects that his instinct as a seven-year-old, to shelter a dying bumblebee rather than stamp on it, was the right one. Of the football, he notes: "I'm starting to quite like it."