08 June 2025

Chris Williamson Explains Why Finding Love Feels Harder Than Ever - The Diary of a CEO with Chris Williamson

In todays moments episode, Chris Williamson dives into why real relationships seem harder to find in today’s world - and what you can do about it. With the challenges of modern dating, and the rise of disconnection, Chris offers a hopeful perspective on how to navigate these hurdles and create deeper, more meaningful connections in your life.

The Loneliness Epidemic and Retreat from Relationships

  • Loneliness is distinct from solitude, which can be enjoyed. The feeling of loneliness is often vague, like a "smell" or an innate sense that something is not right, only becoming clear when genuine connection is finally experienced.
  • The single biggest predictor of health outcomes in life is the number of close connections one has, surpassing exercise and quitting smoking/drinking. People in relationships also experience better health outcomes.
  • Decline in Male Friendships: The number of men reporting six or more close friends dropped from 55% in 1990 to 21% in 2020. Alarmingly, 15% of men now report having zero close friends.
  • Inauthentic Connection: Playing a role (e.g., the party boy or the CEO) means that any praise or love received only applies to the projection, leaving the individual feeling "alone in a crowd and Hollow in Victory" because they were not being their true self. The cure for loneliness is to "show up as myself and to build connection on that basis".
  • Social Retreat: Both men and women are retreating from the mating market, citing the pain and difficulty of the world as justification for remaining single and childless.
    • One in three men aged 18 to 30 has not had sex in the last year.
    • 50% of men aged 18 to 30 are not looking for a committed relationship, a sign of retreat and an "unbelievably extreme statement" for men to make.
    • By 2040, 45% of 25- to 45-year-old women are projected to be single and childless, and studies suggest 80% of involuntarily childless women did not intend to be mothers.

The Tall Girl Problem and Mating Market Imbalance

  • The increase in women's achievement in education and employment, combined with female hypergamy (the tendency to date up or across in status, education, and employment), has created a significant imbalance.
  • 78% of women want a man who is as educated or employed as they are, and they value a partner's socioeconomic status significantly more than men do.
  • As women rise up the competence hierarchy, the pool of eligible men (who meet or exceed their requirements) shrinks, which is termed the "tall girl problem".
  • This imbalance leads to a large group of men being "essentially invisible to women" and causes an increasing cohort of women to compete for a small group of "super high value guys" at the top.
  • These high-value men are often commitment-averse due to the wealth of options, leading to them potentially using and discarding women, which, in turn, causes resentment toward all men, including those who were invisible at the bottom.

The Impact of Me Too and Fear of Approach

  • The Me Too movement was a necessary reckoning to call powerful men to account for misbehaving and using their power for sexual access.
  • However, the movement's consequence has been the sterilization of almost all approach behavior: 80% of men report not approaching women because they are scared of being seen as creepy, while 84% of women still want the man to make the first move.
  • This mutual fear has resulted in an "epidemic of loneliness and sexlessness amongst the sexes".
  • Online dating worsens this problem because it forces optimization on objective metrics (like salary or education), diminishing the value of factors like charm and humor that could be leveraged in person. Furthermore, there are three men for every one woman on dating apps.
  • The public shaming of men on platforms like TikTok for seemingly innocuous actions (e.g., offering help at the gym) causes people to reset expectations and further "Nerf the world", leading to less social interaction.
  • A possible solution is to re-enable in-person dating, which would reduce the tall girl problem by allowing men who are funny or charming, but lack the objective metrics, a chance to gain status in the eyes of women.
  • Flirting is a lost art that requires complex social dynamics that men often haven't developed due to increased time spent online.

The Male Sedation Hypothesis and Technology

  • The historical phenomenon of un-partnered, childless men causing social unrest (Young Male Syndrome) is not increasing in line with the current high rates of sexlessness.
  • The Male Sedation Hypothesis suggests that pornography, video games, and social media are suppressing men out of status-seeking and reproductive-seeking behavior by providing a "titrated dose" of reproductive cues and goal-seeking status within the online world.
  • Although a society of sedated men is arguably marginally better than a dangerous one, it is not optimal and would be detrimental if external threats arose.
  • Digital Addiction: The addiction to technology is a primary challenge, with the phone hijacking the first hour of the day for many. Sleeping with the phone outside the bedroom is recommended as the number one change to prevent immediate engagement with social media.

The Power of Action, Discipline, and Principles

  • Lead with Action: If chronically unconfident, one must lead with action (behavior) first, because self-doubt is strong enough to discount positive thoughts, making positive affirmation ineffective.
  • Discipline is superior to motivation. Doing something in spite of not wanting to do it is discipline. Motivation is great if it arrives, but it is not necessary to achieve results.
  • Small Promises: Building self-trust requires making small promises to oneself that are never broken (e.g., getting up on time, not hitting the snooze button). Breaking promises to oneself damages the relationship one has with oneself.
  • Tiny Steps Compound: The first step must be "so small that you can't say no to it" to prevent the loss of motivation. The goal is to consistently win the routine for decades, realizing that tiny steps compound over time.
  • The "Never Miss Two Days in a Row" Rule: A habit missed once is a mistake; a habit missed twice is the start of a new habit. To maintain momentum, never miss two days in a row.
  • Focus on Principles: Given that the future is varied and difficult to predict, a rigid plan will be destroyed by intense growth or unforeseen changes. Instead, one should adopt a set of core principles (e.g., be mindful, pay attention, tell the truth, keep promises).