In 2009, Robert Webb, best known for the U.K. TV series Peep Show and Back (now on the Sundance channel) and the sketch show That Mitchell and Webb Look, performed on Let's Dance for Comic Relief, dancing to "What a Feeling" from the movie Flashdance dressed as a woman. The performance was watched live by more than seven million people and has since tallied another two million views on YouTube. Webb's touching and funny memoir, How Not to Be a Boy, opens with an imagined conversation between the adult Webb and his 15-year-old self, who, growing up in the conservative, working-class village of Woodhall Spa, in Lincolnshire, England, could never have imagined that performance in his wildest dreams or the long, difficult path his life would take to get there.

Webb came of age in 1980s Lincolnshire. "The message I got loud and clear was that there was only one thing worse than being called a girl, and that was being called gay," Webb says. There were rigid rules for boys: don't talk about your feelings and don't ever cry; fight other boys; and love sports. But Webb was a sensitive kid who preferred poetry to sports. Webb's mother was loving and affectionate, but his father, a woodcutter, was a stern man who cast a shadow over the whole family.

Webb's mother divorced his father when Webb was five—this was a relief, Webb says, because "I was very scared of him"—but when Webb was 17, she died. "My mother was the central influence on my childhood and her death marked its abrupt ending," he says. "She had a tough life and I think I got from her an admiration for stoicism and grace under pressure. There's an idea that being able to ‘keep your head when all around are losing theirs' is an exclusively male trait, and that's obviously ridiculous."

How Not to Be a Boy is a powerful rebellion against old ideas about masculinity. Webb, who moved in with his father after his mother's death and before going to Cambridge, is starkly honest about this period of his life. "I think her death emboldened me," he says. "There was a kind of defiance going on, a kind of ‘Okay, universe, you did your worst, now watch this!' It was a romantic reaction to an unfathomable loss—healthier than self-destruction, though I had suicidal thoughts for the next three years, but flawed in its own way." Nonetheless, Webb, who is now married with two daughters, began to see that he could embrace who he really was.

When asked what advice he'd give to boys today, Webb says, "It's okay to cry if you're in pain. It's okay to be not much interested in sports. It's okay to be a virgin. It's okay to dance. It's okay to be fully committed to friendship and love." Webb recalls his own teenage struggles with these issues in what is perhaps the most moving chapter in the book: "Boys Don't Fall in Love (with Other Boys)."

Though Webb is encouraged by the changes in gender roles and expectations, he still thinks we have a long way to go. In "Act Two," the second half of his book, he debunks common myths—"Men Are Organized," "Men Don't Need Therapy," "Men Understand Women"—to pick apart the way society expects men to be. "If I say ‘doctor' or ‘judge,' what's the picture that flashes into your mind? Is it a woman?" Webb asks. "Men need to see women as fully human and fully equal," he continues. "That sounds simple, but it's depressingly rare. Not equal because they've earned it, or equal because they somehow made it in a man's world. Equal because they were born equal."

And Webb's relationship with his father? Eventually, they found their way back to one another. After his Flashdance performance, Webb found a voice-mail message from his father. "Hello, boy, only Dad. I watched y'dance on the box. Bloody well done. You looked bloody marvelous, Have a pint for me. You know how I feel about you."