How Not To Be a Boy Summary

Why is it okay for women to wear pants, but men can’t wear a skirt? Who decided what boys and girls 'should' be, and how do these expectations shape us?

1. Gendered behavior is socially constructed, not biological.

From a young age, children absorb society's predefined roles for boys and girls. Parents and caregivers frequently, though unconsciously, reinforce stereotypes by labeling behavior as inherently “masculine” or “feminine.” This belief in biologically determined gender differences persists despite evidence to the contrary.

A 2015 Science magazine article debunks the myth of a "male" versus "female" brain. Neuroscience shows that each brain is unique, devoid of clear gender-based partitions. Similarly, Cordelia Fine's research in Delusions of Gender highlights societal bias, such as mothers’ underestimation of their daughters’ physical abilities while overestimating their sons'.

These stereotypes create lasting effects. When boys avoid "feminine" traits like emotional sensitivity, they often grow into men who lack emotional intelligence or relational skills — a learned behavior, not an innate one.

Examples

• A 2000 study revealed mothers routinely underestimated baby girls’ physical abilities compared to boys.
• Gendered toys and activities, like dolls for girls and action figures for boys, reinforce societal roles.
• The myth of boys being naturally less emotional discourages boys from expressing vulnerability.

2. Bullying enforces gender conformity in boys.

Boys face intense pressure to conform to male dress codes, hobbies, and behavior — and bullying is the enforcer. Any deviation from accepted norms, no matter how small, can trigger ridicule or exclusion.

Robert Webb recalls a personal childhood episode when he wore socks deemed "girly." The taunts began almost immediately, leaving Webb to deflect attention by referencing an embarrassing memory of his bully. Though he skillfully navigated playground dynamics, this incident illustrates how relentless gender policing starts young.

This social policing doesn’t just impact wardrobe choices – it teaches boys that survival in the hierarchy demands adopting the dominant gender norms. Showing vulnerability, sensitivity, or individuality isn’t an option.

Examples

• Young Webb being teased for wearing the “wrong” socks at a soccer match.
• The unspoken rule: only plain white socks with minimal stripes are acceptable for boys.
• Webb’s quick retaliation highlights how verbal sparring becomes a defense tactic for boys.

3. Modern gender stereotypes resemble outdated prejudices.

Many assumptions about men and women echo absurd beliefs held about other groups in the past. For instance, boys are dismissed as naturally less emotional or studious, much like outdated views once labeled certain races or religions as “less capable.”

Webb challenges the idea that boys are inherently rougher or less complex than girls. Personal anecdotes, like his brother Mark’s nurturing side (teaching Webb to sing or babysitting), show the emotional richness that can coexist with traditional masculinity.

These rigid stereotypes strip both genders of their full humanity. For example, a boy might suppress his natural gentleness to match society’s expectations of toughness, leaving him disconnected from his true self.

Examples

• Modern biases resemble past race-based stereotypes in framing entire groups as “naturally” one way.
• Webb’s brother Mark taught his younger sibling to whistle but was also a stereotypically macho athlete.
• Assumptions like "boys just don't read naturally" hinder their intellectual development.

4. Boys are taught to value physical toughness over intellect.

Boys grow up believing that roughhousing and physical dominance define masculinity. Intellectual interests, on the other hand, are treated as “unmanly” pursuits. This leaves young men afraid of being labeled “weak” if they excel academically.

Webb’s recollection of weekly play-fights with his brothers shows how physical interactions became a bonding ritual. Yet, his decision to dampen his love for learning to avoid ridicule highlights a damaging tradeoff: boys often suppress their intellectual growth to fit in.

This aversion to braininess is ironic. Society simultaneously expects boys to assume leadership roles as adults but discourages the cultivation of thoughtful, critical thinkers during formative years.

Examples

• Webb’s weekly “ritual fights” with his brothers were affectionate but competitive.
• In school, boys avoided showcasing intelligence to appear “cool.”
• Misguided beliefs about hormones perpetuate the stereotype that teen boys can’t focus on academic work.

5. Boys aren’t encouraged to develop social or emotional skills.

Social expectations paint boys as naturally clumsy communicators, further discouraging their emotional growth. If a rulebook exists for social finesse, boys aren’t handed a copy.

Webb remembers playing chess on a school outing and resisting the urge to correct his opponent’s blatant rule-breaking. Their mutual inability to communicate honestly made the game and friendship tumble fast. This mirrors adult male relationships where avoidance replaces difficult conversations.

From dodging conflict to labeling emotions as weakness, boys grow up ill-equipped for meaningful interactions. Over time, this isolation fosters loneliness and hinders long-lasting connections.

Examples

• Webb and his friend Gareth failed to discuss or resolve their chessboard misunderstanding.
• Webb’s adult friend moved houses to avoid conflict with neighbors over shared trash cans.
• Lack of emotional training discourages men from voicing needs and resolving disagreements civilly.

6. Awkwardness in dating highlights the limits of male socialization.

Teenage boys, fumbling between romantic urges and societal pressure, often make dismal partners. They aren’t taught how to discuss feelings or navigate mutual respect in relationships.

Webb’s first love, Isabel, experienced the full brunt of his uncommunicativeness: he ignored her socially, avoided meaningful conversations, and offered shallow apologies to avoid losing the perks of the relationship. Instead of breaking up with honesty, he waited for her to leave him.

Dating showcases how ingrained male behavioral norms cause frustration for all involved, reducing relationships to transactional dynamics rather than meaningful connections.

Examples

• As a teen, Webb refused to spend time with Isabel’s friends or engage in deep discussions.
• Isabel’s love letter offered a chance for honesty, but Webb continued the charade for convenience.
• Webb reflects on how male pride and avoidance shaped his relationships.

7. It’s healthy and normal for men to cry and explore emotional depth.

Contrary to stereotypes, men can and do engage deeply with their emotions – they just need permission to do so without judgment. Whether seeking comfort from friends or acknowledging non-heteronormative relationships, Webb advocates for men to embrace their complexity.

When Webb cried after his mother’s death, his friend Will offered support in a traditionally "unmasculine" manner. Their moments of physical and emotional intimacy convey how freeing it is for men to ignore societal rules and express genuine connections.

Embracing feelings enables men to deepen their understanding of themselves and others – an essential step toward building healthier relationships.

Examples

• Webb crying in bed while his friend Will held his hand and reassured him.
• Webb and Will explored a tender, sexual relationship despite identifying as straight men.
• Friendship between the two persisted, evolving into road trips and shared cultural experiences.

8. Poor emotional expression leads to tension and disconnection.

Men often struggle to express love in words, defaulting instead to actions or control. These tendencies, though well-intentioned, can create misunderstandings.

For Webb, his stepfather's guilt trips and his biological father’s obsessive tidiness barely masked their affection for him. However, the lack of vulnerability in their interactions often resulted in frustration and angry outbursts.

Learning to communicate love directly — rather than through disciplinary measures or controlling tendencies — is something many men, including Webb, grapple with as they evolve.

Examples

• Webb’s stepfather tried to guilt him into staying home by invoking his late mother’s wishes.
• His biological dad expressed love in over-detailed housekeeping tasks, leading to arguments.
• Misunderstandings between Webb and his fathers were fueled by society’s definition of masculinity.

9. Redefining masculinity benefits everyone.

Rejecting narrow ideas of what it means to be a man allows boys and men to live freer, fuller lives. Masculinity can encompass emotional attachment, creativity, care, and vulnerability just as much as physical strength or leadership.

Webb encourages letting boys express individuality instead of confining them to strict gender norms. Beyond personal growth, this can produce kinder partners, more attentive parents, and healthier communities.

Society thrives when people aren’t forced into choking categories. By allowing men to be human, everyone benefits.

Examples

• Webb shares that being a father brought new awareness, pushing him to erase outdated male rules.
• Men embracing emotion strengthens family units and community bonds.
• Loosening gender norms helps reduce toxic masculinity and societal harm.

Takeaways

1. Support boys in exploring activities and emotions outside societal "norms" to foster individuality.
2. Actively reject stereotypes in your language and expectations around both men and women.
3. Practice open communication and vulnerability, regardless of how uncomfortable it may seem at first.