Lost Boys: A Generation Z Journey

Becoming Men in the 21st Century

Note: This article contains generalizations and societal observations that may not apply to everyone. Individual experiences vary widely. The purpose is to discuss broad trends, provoke thought, and suggest possible steps forward for men who feel unsure about their path.

Introduction: The Landscape of Lost Men

Over the past few years, social scientists, dating coaches, and everyday observers have noted a striking trend: a growing number of young men from 18 to 27—particularly those classified as Generation Z—report never having approached a woman romantically. Polls and anecdotes even suggest that as many as 50% of young men in this demographic have never initiated face-to-face contact with a woman to express romantic or sexual interest.

Why is this phenomenon happening? We live in a time when virtual encounters often replace in-person interactions, and the fear of rejection can loom larger than ever. Technology simultaneously promises easy connection and amplifies the anxiety around real-life confrontation. Moreover, shifting cultural norms about gender and relationships have left many men confused about their place in society. In particular, three factors often arise in discussions:

1. A Lack of Overarching Mission. Many Gen Z men feel unanchored, uncertain about their goals and place in the world, which diminishes their confidence in dating and social situations.

2. The Impact of Hypergamy and Social Media. Social media can heighten women’s selectiveness (and men’s, too) by constantly showcasing “the best” potential partners, fueling comparisons and illusions of “better options.”

3. The Absence of a Rite of Passage. Throughout history, young men had structured rites of passage or challenges signaling the transformation from boyhood to manhood. Without any clear modern equivalent, many feel stuck in an extended adolescence without a defining moment that marks their entry into mature masculinity.

Simultaneously, a biological and cultural narrative persists: women’s peak years of fertility and feminine expression are in their 20s, whereas men often come into their own in their 30s and 40s. This mismatch in timelines can create confusion about relationships, marriage, and dating “strategy,” especially when dating apps expand social circles and compare everyone to everyone else.

In the following sections, we will delve deeper into these issues, examine how they affect Gen Z men, and propose a possible “game plan” to help young men transform lost years into a foundation for a strong, fulfilling manhood. We’ll also consider the idea that men “age like wine,” culminating in higher desirability and stronger identities as they grow older—if they put in the work.

1. A Cultural Shift: The Rise of the Lost Gen Z Man

The term lost men might sound dramatic, but it captures a widespread feeling of disconnection that many Gen Z men experience. Digital technology has changed how we date, learn, socialize, and even work. As every aspect of life becomes more digitized, some young men report an increasing sense of isolation. Unlike previous generations, who often had more straightforward paths—such as finishing high school, starting a job or attending college, finding a partner, and settling down—Gen Z’s path is often murkier.

• Delayed Markers of Adulthood: Fewer Gen Z men are in stable careers by their early 20s. Rising costs of living and extended education push financial independence further down the road.

• Changing Gender Expectations: Traditional masculinity is questioned more frequently, and men can feel unsure what traits society wants or tolerates—strength, ambition, or vulnerability?

• Online Social Circles: Many social interactions now begin or occur solely online. Without in-person practice, men may have trouble forging real-world confidence, particularly in romantic pursuits.

Beyond these social changes, there’s also an underlying existential vacuum. Modern society lacks communal rituals—such as military service, structured apprenticeships, or community rites of passage—that once signified a boy’s transition into manhood. Instead, we have an unstructured environment where one might turn 18 or 21 and find that there is no clear test, no definitive moment of transformation.

2. The Mission Impossible from the 20s

Historically, a young man’s 20s were a time of intense focus on establishing oneself: learning a trade, starting a family, and proving competence to a community. The path was more linear. Today, career landscapes have changed so much that many in their 20s are still exploring, job-hopping, or even living at home.

How does the lack of a clear mission or purpose impact romantic pursuits? Confidence and self-assuredness often stem from knowing one’s direction. If a man feels aimless—uncertain about his career, education, or personal development—it can be daunting to approach a woman and present himself as a worthy partner. The internal voice of doubt says: “You don’t even know what you want to do with your life. How can you approach someone and offer value or stability?”

Additionally, with social media showcasing the extravagant lifestyles of influencers or individuals with high economic status, young men may feel incompetent by comparison. In an era of highlight reels—perfect photos, success stories, curated lives—it is easy to believe you are “behind” or “not enough,” especially if you haven’t locked down that dream job or that glamorous social life.

Constructing a Personal Mission

To combat this, Gen Z men might focus on designing a personal blueprint for their 20s. This doesn’t need to be rigid or final. The important thing is to develop a sense of direction. Some starting points:

1. Identify Core Values: What do you truly care about? Adventure, family, innovation, service, creativity? Choose a few guiding principles to shape your decisions.

2. Set Measurable Goals: Whether it’s finishing a degree, saving a certain amount of money, or launching a personal project, map out tangible short-term steps that reflect your values.

3. Cultivate a Growth Mindset: Recognize that your 20s are a training ground. Rather than focusing on comparison or immediate success, concentrate on skill-building and character development.

By actively working toward a chosen mission, men often find that their sense of self-worth and clarity increases. This resonates outward in social and romantic interactions, making them more appealing partners.

3. Hypergamy, Social Media, and the Revolving Door

Hypergamy refers to the concept—often discussed in evolutionary psychology and sociology—that women, on average, tend to seek partners who are equal to or higher than themselves in status, resources, or other desirable traits. While this is a broad generalization, social media has amplified the sense that everyone is looking “upward” for the best possible option, leaving many potential pairings unnoticed or dismissed.

Social Media’s Amplification of Hypergamy

• Endless Options: Dating apps and Instagram can give the illusion that there is always a better match just around the corner, fueling indecision and less willingness to commit or even try.

• Highlight Reels: People primarily post their best photos and achievements. This curated portrayal can make men (and women) feel they do not measure up.

• DM Culture: With direct messages, a charismatic or wealthy individual can easily contact someone who lives across the country or even the world. The local dating pool is no longer the only resource. Thus, high-status men can theoretically “poach” women from any location, intensifying competition.

For men who are still developing their sense of self or establishing their financial and social standing, this environment can be intimidating. Observing that women their age might be drawn to men with more social proof, resources, or life experience can deter them from approaching. They might fear an automatic rejection or believe that the “competition” is too fierce.

The Revolving Door in the 20s

The phrase revolving door of men references situations where some women in their 20s go through multiple relationships or flings, exploring and experimenting with different partners. This dynamic can be partly attributed to:

1. Exploratory Phase: The 20s can be a time when many people, men and women alike, aren’t looking for a long-term commitment. They’re learning what they want and do not want.

2. Upward Social/Financial Aspirations: As they meet new people—often through social media—young women may end relationships or casual connections to see if someone else better fits their needs or desires.

3. Cultural Acceptance of Casual Dating: Modern culture, especially in certain urban environments, normalizes short-term dating or hooking up, making it less common for individuals to settle early.

This revolving door can leave some men feeling discouraged or jaded. If they do not fit the currently coveted ideal—perhaps a man in his 30s or 40s with more resources—they may find it challenging to even get started. This frustration can become a feedback loop: fear of rejection leads to avoidance, which leads to even less social or romantic experience, which leads to more fear.

4. The Missing Trial: Rites of Passage in Modernity

One of the most consistent points in discussions about masculinity is the absence of formal rites of passage for young men. Across many cultures and throughout history, there were clear markers: warrior initiations, hunting tests, or communal ceremonies. These challenges served to test and strengthen young men physically, mentally, and emotionally. Upon completion, society would recognize them as men, granting new status and responsibilities.

Why Trials Matter

• Psychological Transition: A rite of passage signals that you’ve faced adversity, conquered it, and earned your place as a contributor to your community.

• Bonding with Mentors and Peers: Traditional trials often took place in groups, overseen by community elders, forging strong bonds among young men and providing them with mentors.

• Clear Expectations: After the rite, a young man typically knew what was expected of him—protecting or providing for the community, starting a family, or taking on leadership roles.

In modern times, we rarely see such structured challenges. Some men join the military, which can serve as a rite of passage. Others might find initiation in sports or extreme physical endeavors. But many do not experience a moment that definitively transitions them from boy to man.

Consequently, a 25-year-old might feel psychologically closer to a teenager if he’s never been tested or faced substantial hardship. This can translate into diminished confidence, lack of direction, and a hesitance to take risks—like approaching a potential romantic partner.

5. Biological Timelines: Men Age Like Wine, Women Peak in Their 20s?

A popular phrase states men age like wine, women age like milk, though this is typically a crude oversimplification. A more measured perspective is that men often reach their peak physical, financial, and social influence in their 30s and 40s—particularly if they’ve invested in themselves, built a career, and maintained their health. Women, meanwhile, are biologically primed for peak fertility in their 20s, though of course women can be vibrant, powerful, and attractive well past their 20s.

Yet these biological tendencies can affect dating patterns:

1. Early 20s Focus on Exploration: Since women may be perceived (or perceive themselves) as having many options in their 20s, they might explore before settling down. Men, conversely, who haven’t yet built their status or personal confidence might struggle to compete for these women’s attention.

2. 30s to 40s Prime for Men: By the time many men reach their 30s, they have more career stability, confidence, and social status, making them more attractive to younger women. Some men naturally prefer to wait until these prime years to build families, capitalizing on this advantage.

3. Shifts in Age Preferences: Younger men (18–27) often face a mismatch: they might be interested in women their age, but feel overshadowed by older male competition. Meanwhile, women in their 30s or 40s might look for men either their age or older, or sometimes younger, depending on personal circumstances.

The net effect is that men in their 20s can feel left out, while men in their 30s or 40s might feel they finally come into their own. However, none of this is automatic—growth and self-development are paramount.

6. Trials for Women: Menstruation as a Rite,“Madien, Matrodon, Matriarch”

Some argue that women’s monthly cycle, pregnancy, or childbirth naturally bestow a form of rite of passage that men do not experience. While these are real physical and emotional challenges, it’s crucial to note that not all women see these events as a direct path to self-actualization or social acknowledgement of adulthood. However, one could say that the regular hormonal and physical changes might foster a sense of groundedness in their bodies and life stages that men do not organically undergo.

For men, the answer is not to envy women’s biological rites, but to create or find tests of their own. This can happen through:

• Sporting Achievements: Marathon running, martial arts competitions, or team sports that demand discipline and perseverance.

• Skill Mastery: Learning a craft to a high level—musical performance, carpentry, coding, or any domain requiring extensive effort and eventual public demonstration.

• Personal Challenges: Solo travel, wilderness survival courses, or volunteer work in challenging conditions—anything that requires stepping outside comfort zones.

The key is to choose a challenge that requires sacrifice, resilience, and growth, marking your own personal rite of passage.

For some men observing these transitions, it’s easy to become resentful: “Why are these women ignoring me in their Maiden stage? They’ll only come around when they are ready to settle.” But recognizing that people have different life phases can ease resentment. Everyone has a right to explore, grow, and change. Men also go through phases, and acceptance of this cyclical nature may reduce frustration.

7. Building a Personal Trial: A Game Plan for Lost Men

Step 1: Self-Awareness and Vision

1. Journal Regularly: Spend 10–15 minutes each day reflecting on your thoughts, goals, and experiences. This quiet introspection will reveal patterns, fears, and desires.

2. Define Core Values: Write down your top 5 values—integrity, adventure, creativity, discipline, etc. These guide every decision and help maintain alignment.

3. Visualize Your Future: Imagine where you want to be at 30, 35, and 40. What kind of man do you see yourself as? Successful entrepreneur, devoted husband, world traveler, community leader? This exercise clarifies the path ahead.

Step 2: Physical and Mental Training

1. Fitness Regimen: Choose a fitness program that challenges you—weightlifting, martial arts, rock climbing. Aim for at least 3–4 sessions per week. Physical strength and discipline build confidence.

2. Mindset Practice: Consider activities like meditation, breathwork, or mindfulness to reduce anxiety, boost concentration, and cultivate inner calm.

3. Educational Growth: Read widely. Study biographies of great men, learn new skills relevant to your interests or career, and keep a curious mind.

Why this matters: A trial needs a physical and mental dimension. Through discipline and daily practice, you’ll see tangible progress, reminding you that you can set a goal and conquer it.

Step 3: Social and Emotional Skills

1. Practice Approaches: Start small. Make casual conversation with strangers in low-stakes environments—a coffee shop, bookstore, or gym. Your goal isn’t to find a date immediately but to become comfortable initiating interactions.

2. Emotional Intelligence: Learn to understand body language, practice active listening, and be aware of your own emotional triggers. This fosters deeper, more genuine connections.

3. Circle of Mentors and Allies: Seek out older mentors or friends who model the kind of man you want to be. Join meetups or groups aligned with your interests, sports teams, volunteer organizations—places where you can forge meaningful bonds.

Step 4: Economic and Life Strategy

1. Career Development: Identify a skill set that the marketplace values. Pursue certifications, apprenticeships, or advanced degrees if needed. Earning potential and professional competence boost your self-assuredness.

2. Financial Habits: Follow a basic budget. Learn investing basics (index funds, real estate, or even starting a small business). Early financial discipline sets you up for a stable 30s and 40s.

3. Lifestyle Design: Where do you want to live? How do you want to spend your daily life? Make choices that support growth, from the city you reside in to the people you spend time with.

Ultimately, your 20s become a training ground for your 30s. By building a sense of financial and professional competence, you’ll approach relationships from a position of strength and genuine self-belief.

Step 5: Consistency and Assessment

Every 6 months, take stock of your progress:

• Physical: Are you stronger? Healthier? More athletic?

• Professional: Has your income, knowledge, or job satisfaction improved?

• Social: Are you more comfortable in new social settings? Do you approach conversations confidently?

• Character Growth: Are you more patient, disciplined, or decisive?

If certain areas are lagging, adjust your focus. The key is consistent, incremental improvement. Over time, these small victories become the trial by fire that shapes your identity.

8. Relationships and Dating: Practical Advice

For many Gen Z men, the immediate concern is how to approach dating in a world that seems hyper-competitive and skewed by social media. Here are some pragmatic suggestions:

1. Focus on Shared Experiences: Instead of a random cold approach at a bar, look for environments where you share genuine interests—like a sports club, coding meetup, or language exchange. Common ground reduces anxiety and fosters a natural conversation starter.

2. Assertive Communication: When you do approach someone, be direct and respectful. A simple “I noticed you and wanted to say hi” can suffice. Overly complex pickup lines often come off as inauthentic.

3. Manage Rejection: Understand that NO is not a personal indictment. Attraction is subjective. If you’re polite, you lose nothing by trying. Each approach is valuable practice in social dynamics.

4. Limit Social Media Comparison: Reduce time spent scrolling Instagram or TikTok. Exposure to curated highlights can distort your self-image. Keep your primary focus on your real-world experiences and growth.

5. Set Boundaries: If someone’s behavior—online or offline—makes you feel belittled or drains your energy, step away. Healthy relationships require mutual respect and positivity.

As you grow personally and professionally, your confidence in dating scenarios will likely expand. You’ll carry yourself differently, and potential partners sense that energy.

9. Beyond the 20s: Embracing the Journey

While the 20s can be fraught with insecurity and confusion, it’s essential to remember that life does not end at 30. In fact, many men only start hitting their stride in their early-to-mid 30s. Viewing your 20s as a “boot camp” or “training arc” can alleviate some pressure. You don’t need to have everything sorted out by 25.

If men “age like wine,” that quality is earned, not automatic. Wine improves under the right conditions—temperature, environment, time. Men similarly develop with the right inputs: discipline, self-awareness, mentorship, and perseverance. A man who does not invest in himself might “age like vinegar,” so to speak.

10. Balancing Traditional and Modern Values

One challenge Gen Z men face is reconciling traditional ideas of masculinity—providership, stoicism, strength—with modern expectations of emotional openness, equality, and adaptability. Here are some points of balance:

• Strength in Vulnerability: Admitting fears or anxieties does not diminish your masculinity if done in a context of wanting to learn and improve.

• Leadership and Partnership: Leading doesn’t mean dictating. In relationships or teams, you can provide structure or protection while still inviting collaboration and acknowledging others’ strengths.

• Respect and Assertiveness: You can be polite, respectful, and mindful of boundaries while still being assertive about your goals, desires, and values.

A balanced modern masculinity respects women’s autonomy and equality while maintaining a man’s drive and responsibility for self-betterment.

The Road to Manhood

Gen Z men who feel lost or hesitant about approaching women, or unsure of their place in society, are not alone. Cultural shifts, social media, and the erosion of traditional rites of passage have created an environment where half of young men might not even attempt to initiate a date. However, the solution is neither withdrawal nor cynicism. Rather, it involves:

1. Cultivating a Purpose in your 20s—an anchor that gives meaning to your daily actions and achievements.

2. Understanding the Role of Social Media and Hypergamy, without letting it deter you, by focusing on your personal growth rather than external validation.

3. Establishing Your Own Trials—structured challenges or rites that force you to grow physically, mentally, and socially, forging your path to manhood.

4. Accepting Biological and Cultural Timelines, while leveraging your 20s as a foundation for your 30s and 40s, where many men find their true prime.

5. Practicing Balanced Masculinity, combining traditional strengths like responsibility and discipline with modern traits like emotional intelligence and mutual respect.

At the heart of this journey lies the realization that manhood is not bestowed by age alone. It is achieved through continuous testing, self-reflection, and perseverance. By taking deliberate steps to shape your body, mind, career, and social skills, you effectively create your own rite of passage. And as you evolve from a young man into a man of substance, you will discover that the challenges of your 20s become the bedrock of a confident, purposeful life in your later decades.

Remember: Trials and hardships are not roadblocks but stepping stones. In forging the path toward a mature, grounded masculinity, you build the resilience and wisdom that will serve as your compass—both in romantic pursuits and in every other aspect of life. Your 20s can be a crucible that hardens you into a man ready to embrace the vast possibilities your 30s, 40s, and beyond will bring.

Final Note

No single approach fits every individual, but taking ownership of your personal development is a universal principle. Whether through physical challenges, career milestones, creative projects, or social endeavors, each step that demands effort and dedication carves out your unique identity as a man. Embrace the journey, learn from your failures, and you will find your way—stronger, wiser, and ready to engage with the world on your own terms.

By Noel | Fowklaw