About this Author
Robert Webb is an actor and comedian known for his roles in popular, award-winning series such as That Mitchell and Webb Look and Peep Show.
Biographies & Memoirs
13:20 Min
Conclusion
7 Key Points
Conclusion
Gender stereotypes are deeply rooted in society. These expectations shape how boys and girls behave and think. Men and women can express emotions and have diverse interests. Breaking these stereotypes allows individuals to be themselves and accept their true potential.
Abstract
Robert Webb's reflections on gender explore how societal expectations, not biology, largely shape behaviors and identities. In How Not to Be a Boy, Webb examines how stereotypes about toughness, intelligence, and emotions harm boys and men. He recounts personal experiences—from strict dress codes and bullying to struggles with communication and emotional expression. Webb also challenges ideas of masculinity by sharing moments of vulnerability and exploring sexuality. By addressing outdated beliefs, such as men being unemotional or less nurturing, Webb urges society to accept individual uniqueness and dismantle harmful stereotypes, proving that gender norms can—and should—be redefined for healthier lives.
Key Points
Summary
Gender Differences Are Mostly Shaped by Society, Not Biology
Most differences in behavior between genders are not due to biology. Instead, they are influenced by social expectations. Parents don't usually aim to be bad, but many unknowingly reinforce gender stereotypes. For example, a parent might say, "Sally is such a girl" when describing how she played with a toy. One time, a boy tried to get her to play with an action figure, but she just dressed it up and tucked it into bed. What parents don't always realize is that even if a child adopts certain behaviors, it doesn't mean they are biologically hardwired to act that way. Most cognitive and behavioral traits are not tied to gender at all. There's no such thing as a "male brain" or a "female brain." In a 2015 article from Science Magazine, neuroscientists explained that every brain is unique, and no brain can be classified by gender.
So, when a boy refuses to wear a pink sweater, it's not because of biology. The differences we see are often the result of society's expectations. Psychologist Cordelia Fine, in her book Delusions of Gender, refers to a 2000 study that shows how biased society is about gender. In this study, mothers were asked to judge how steep a slope was and whether their 11-month-old toddler could climb it. The results showed that mothers often thought girls couldn’t climb as steep slopes, even when they could, while they overestimated the abilities of boys, thinking they could handle steeper ones than they actually could. With such biases around, it’s no surprise that men and women end up having different personalities.
Strict Dress Codes and Gender Stereotypes
Boys often face strict dress codes, and the pressure is increased by bullying. For example, women have been wearing pants for over a century, but it’s still considered odd for men to wear skirts or dresses. Why is that? Boys are expected to follow very specific clothing rules. When Webb was 10, there was a big problem when his aunt True tried to give him socks that were meant for girls before a soccer game. Webb couldn’t believe it. He thought they were wrong because they were too long and had patterns on them. Didn’t his aunt know that the only acceptable socks for a boy on a playground were plain white ones, with maybe a black stripe at the top?
Sure enough, when Webb’s friend Matthew Tellis saw the socks, he started laughing and calling Webb a girl. Soon, the other boys joined in and mocked him. This strict dress code for boys is often enforced by bullying, so most boys learn to respond quickly to such situations. Webb was no different. He didn’t let the teasing slide. Instead, he joked that Matthew would like the socks more if they were covered in dirt, referring to an embarrassing incident.
One time, Matthew had rushed out of class to the bathroom and, trying to follow the teacher's strict 20-second rule, accidentally came back with some of his business still on his pants. Webb used this memory to turn the attention away from his socks and back onto Matthew’s accident. All of this bullying and teasing happens because of society’s unnecessary gender stereotypes.
Break Gender Stereotypes
It's surprising, but many pregnant women still face the assumption that they’ll quit their jobs once they have a baby. Similarly, some people are shocked when they see a man taking care of his young child in a café. These are examples of outdated and unreasonable beliefs about gender. The silliness of these stereotypes becomes clear when you think about how people once held incorrect ideas about race and religion.
For instance, it's common to hear things like, "Mark is like all boys, he can't sit still." Sure, boys can learn to enjoy reading, but it’s not automatic. Or how about, "Men are great because they're simple, with no messy emotions to handle." Imagine if someone said the same about Muslims or Asians. People would consider it offensive, and that’s how gender stereotypes should be viewed too. These broad statements are just wrong, as anyone who understands human behavior knows.
Take Webb’s brother, Mark, as an example. He fits the typical image of a man—he’s a father, coaches a boys' soccer team, drives an Audi, and works as a manager in an agricultural company. In school, he even got tough and sometimes violent to earn respect. But Webb remembers Mark as a kind person who took time to teach him to sing and whistle. Mark also helped take care of Webb when their mom was busy, and one night, he even kissed Webb goodnight on the lips. So, don’t fall for the stereotype that men can’t be emotional or nurturing—because they absolutely can be.
Societal Expectations for Boys: Toughness Over Intelligence
Society often expects boys to prefer physical, rough activities over intellectual pursuits. There are specific, and sometimes funny, ideas about how boys should behave. They are supposed to act tough, keep a calm and confident face, and handle situations without showing weakness, especially when interacting with other boys or men. From childhood, boys are encouraged to play roughly. For instance, Webb, who grew up in rural England with two older brothers, experienced this regularly. At the kitchen table, his brother Andrew would sometimes push his head—sometimes lightly, other times hard enough to dunk his head into his cereal bowl. Every Tuesday, the brothers held "ritual fights" in Andrew’s room, playfully wrestling until Webb would often hit his head on something hard but pretended it didn’t hurt to seem tough.
Boys are also taught not to show pain or emotions like crying. On top of this, they are discouraged from showing interest in intellectual activities, as being smart is often seen as uncool or unmanly. This belief is strange, considering boys are expected to grow up and take on important roles. However, in school, boys who enjoy academics risk losing their "cool" status. Many assume that excelling in school is incompatible with being good at practical activities like sports.
This attitude results in the idea that intellectual activities are not masculine. It also aligns with the false belief that teenage boys’ hormones make it harder for them to focus on school or follow rules. The notion that being good at studying is unmanly can harm boys’ academic progress. Bullying or teasing for getting good grades discourages boys from developing strong study skills or pursuing academic success.
The Impact of Poor Communication Skills on Boys and Men
Boys are often not taught how to communicate effectively, which can lead to men avoiding social situations. Take Webb, for instance. One day, while on a school bus heading to an outing, Gareth, a classmate, approached him with a chessboard. Webb didn’t expect Gareth to be into chess, but he agreed to play. Webb started the game correctly by moving a pawn two squares forward.
Gareth, however, broke multiple chess rules by placing his queen in the spot Webb’s pawn had just vacated. Webb knew this was against the rules but didn’t say anything. Instead, he played along for a few more moves until Gareth confidently announced “Checkmate.” When Gareth wanted to play another game, Webb declined, leaving Gareth upset. This situation shows how boys often fail to communicate openly. Webb could have easily explained the rules to Gareth, turning it into a learning experience and a proper game, but boys typically struggle with this type of interaction.
Unlike girls, boys usually aren’t expected to develop strong social skills, which leads to problems as they grow older. Webb later heard a story from a friend whose neighbors had been using his trash cans. Instead of addressing the issue directly, the friend decided to move to another house in the same neighborhood just to avoid the conflict. This lack of communication training often leaves men with two options: avoiding problems or responding aggressively. Since fighting is not acceptable, avoidance becomes the norm, sometimes leading to extreme actions like moving houses over minor disputes. Over time, this tendency to avoid conflict can result in loneliness and isolation.
Male Socialization Creates Bad Boyfriends
Teenage boys are often awkward, overconfident, and torn between fearing and wanting sexual experiences. Despite this, many still enter relationships. However, being in a relationship doesn’t automatically make them better partners. Male socialization often leads to boys being poor boyfriends. At 17, Webb began dating Isabel, his first girlfriend. For the first two weeks, the relationship seemed fine, but soon Webb’s bad behavior surfaced. He ignored Isabel at school, criticized her friends, refused to spend time with them, didn’t laugh at her jokes, and never asked about her life. The main issue was that Webb didn’t love Isabel but lacked the communication skills to handle the situation. When Isabel wrote him a heartfelt letter asking if he truly cared about her or was staying just for physical reasons, Webb had a chance to be honest and end things respectfully.
Instead, Webb wrote back a love letter, convincing Isabel he was sincere. This highlights a common problem—some boyfriends don’t know how to break up properly. Webb avoided ending the relationship because it required honesty, bravery, and the ability to give up physical intimacy, all of which he lacked. Webb chose to wait until Isabel became frustrated and ended things herself. He didn’t want to work on the relationship or lose its benefits. Eventually, Isabel grew tired of his lack of meaningful communication and dumped him, which was exactly what he had been hoping for all along.
Men Can Cry and Explore Their Sexuality
It’s completely normal for men to cry, and even heterosexual men can have sexual experiences with other men. Maybe you’ve seen a grown man cry—perhaps during an emotional moment in a movie or while listening to a Bruce Springsteen song. Even if this happens, most men don’t want others to see them cry because it’s often seen as unmanly. But when they’re alone, men can express their emotions freely, including crying. When Webb was 17, he found himself lying next to his friend Will in bed, crying. Webb’s mother had just passed away from cancer, and at that moment, the full weight of her death hit him. Will, however, wasn’t bothered by Webb crying. Instead, he comforted him by holding his hand while a Prince song, Sometimes It Snows in April, played in the background.
In a safe, comfortable setting, men can do more than just cry—they may even explore their sexuality. Even a straight man can have a sexual experience with another man, especially if it’s someone they feel emotionally connected to. Webb had a crush on Will, and as they lay together, something unexpected happened. Webb sexually touched Will, and Will didn’t pull away. It could have been out of curiosity or just affection, but either way, they shared an intimate moment. Years later, the two met again, and when Will touched Webb, he didn’t resist. These encounters weren’t wild or intense, but their bond was filled with strong feelings. Their romance ended when Will fell in love with a woman but they remained close friends. They enjoyed traveling together, having deep discussions about culture, and joking around by doing impressions of their friends.
Men Struggle with Expressing Emotions and Communication
Men often have difficulty expressing their emotions, and this can lead to awkward situations. For example, some men might show their love in odd ways, like being overly critical or controlling. It’s a common stereotype, but it reflects a real struggle with communication. Webb experienced this firsthand when, after his mother passed away, he decided to live with his biological father for a while. This meant leaving behind his stepfather, Derek, and his younger sister, Anna Beth.
Derek felt sad about Webb leaving but didn’t openly say so. Instead, he tried to make Webb feel guilty by saying Anna would be lonely and claiming that Webb's mother would have wanted him to stay. This guilt trip frustrated Webb, and it didn’t change his decision to leave. However, as Webb was leaving, he noticed the genuine sadness in Derek’s voice when he said, “We’ll miss you.”
Living with his biological father brought new challenges. Webb’s dad had a different personality, one marked by extreme neatness and strict routines. Over time, his father’s obsession with cleanliness became overwhelming. He insisted on scrubbing empty milk bottles before setting them out for the milkman and cleaning the bathtub immediately after every use. These rules often led to arguments, with slamming doors and angry words. After moving out to attend Cambridge University, Webb pursued a career in acting and comedy. Reflecting on his experiences as a writer and a father, he realized that being a man doesn’t mean you have to be bad at communication.
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