Modern Wisdom #1016 – Rob Henderson

Is Having a Boyfriend Cringe Now?
Host: Chris Williamson | Guest: Rob Henderson | Date: November 6, 2025

Overview

In this episode, Chris Williamson and Rob Henderson dissect a trending cultural question: “Is having a boyfriend cringe now?”—prompted by a viral Vogue article. They explore the shifting attitudes toward relationships among young women, focusing on the deeper evolutionary, psychological, and socioeconomic mechanisms underlying “anti-boyfriend” sentiment online. Their conversation touches on luxury beliefs, intrasexual competition, reproductive suppression, and social media-driven social dynamics, drawing on both evolutionary psychology and contemporary digital trends. The discussion is insightful, often humorous, and challenges the surface narratives of solidarity and independence that dominate much of today’s cultural commentary.

Key Themes & Discussion Points

1. Setting the Scene: The Vogue Article and Social Shifts

• [01:37] Chris introduces the Vogue article headline: “Is Having a Boyfriend Cringe Now?”.

• Rob recounts seeing the article proliferate across social media, noting its striking popularity and triggering of commentary, especially among “influencer” women.

• Quote (Rob, 01:42):

  “...these women themselves are in relationships. And, you know, she would ask, well, why are you promoting these ideas? These women would say, well, I don't want to seem boastful, I want to show solidarity with single women.”

• Key Insight: The idea of ‘having a boyfriend is embarrassing’ serves both as a personal brand strategy and a social signal, especially among women with influence.

2. Linking to Evolutionary Psychology: Intrasexual Competition & Reproductive Suppression

• [03:00 – 07:00] Rob connects the trend to evolutionary strategies where women may discourage each other from pursuing relationships (“reproductive suppression”) under the veneer of solidarity.

• Quote (Rob, 04:08):

  “...I define luxury beliefs as ideas and opinions that confer status on the affluent while inflicting costs on the less fortunate...by promoting these views, they're actually reducing pathways to happiness for other people.”

• Key Insights:

  • Elite or affluent women are more likely to discourage relationships publicly, although privately they maintain traditional family structures.
  • Happiness data point: women who are married with children report the highest happiness.

3. Branding, Social Media, and Modern Relationships

• [07:06 – 13:13]

  • Chris discusses how online “brand” is now central; relationships are seen as “brand collaborations” rather than emotional or social unions.
  • Quote (Chris, 07:59):

    “Most relationships now are more brand collaborations than they are meaningful connections.”

  • Fear of social embarrassment or appearing “boring” by posting about a boyfriend potentially costs online women their followers—especially both male “orbiters” and other women.
  • Goodhart’s Law: “What gets measured gets managed”—online engagement metrics become relationship proxies.

• Notable Moment:

  • The “swag gap” is touched on later, linking appearance/status signaling in relationships to social branding.

4. Solidarity, Luxury Beliefs & The ‘Inner Citadel’

• [15:41+]
  • The concept that if someone can’t get something (‘boyfriend’, family, wealth), it is reframed as undesirable.
  • Rob’s “Inner Citadel” (borrowed from philosopher Isaiah Berlin): reframing desires to avoid envy.
  • Quote (Chris, 16:01):

    “If you can't get what you want, you must teach yourself to want what you can get.”

5. Subtlety of Female Intrasexual Competition

• [16:09 – 24:05]
  • Rob introduces Tanya Reynolds’ “bless her heart effect”: women’s indirect, plausibly deniable methods of suppressing rivals.
  • Behaviors like discouraging relationships, subtle gossip framed as concern, or emphasizing red flags are ways to limit mating competition.
  • Quote (Rob, 23:34):

    “If you can't get something, you train yourself to not want it, or you teach yourself that this is undesirable.”

6. Cultural and Hormonal Reproductive Suppression

• [28:16+]
  • Rob elaborates on the cultural and physiological processes by which reproduction is discouraged in women (e.g., birth control, stress, comparative standards for parenting/lifestyle).
  • Elite women shape the discourse around parenting and family formation, often setting standards out of reach for less wealthy women, which can add stress and suppress fertility.
  • Quote (Rob, 34:52):

    “...elite women, high status women, say this is what a successful family looks like and you need to be able to afford all of this...if people lower down the ladder think, well okay, that's what success looks like. And if I can't do that...I don't want to be a mother who can't give my kids everything that, that, that is expected of me.”

7. Luxury Beliefs, Elite Hypocrisy, and Social Messaging

• [47:47+]
  • Chris reads an excerpt from Rob’s article: elites who bash capitalism often privately pursue career/wealth, or have partners and children, yet don’t advertise these facts.
  • Performative advocacy: media celebrates stories of women leaving traditional relationships (e.g., “I left my husband for OnlyFans and I’m happy”) but rarely air the reverse narrative.
  • Quote (Rob, 51:22):

    “I asked this magazine editor, would you guys run the reverse story? ...He said, oh, we would never run that, like, not in a million years. And I find this absolutely fascinating...”

8. Ultimate vs. Proximate Explanations

• [36:58; 61:19]
  • Distinction between the stated, conscious motivations (proximate) and the deep evolutionary, often unconscious motivations (ultimate) behind behaviors.
  • Quote (Chris, 36:58):

    “Very rarely are we aware of what the ultimate reasons for our behavior are ... you are much more effective at deceiving other people if you also are deceived by the motivation that you’re doing this through.”

9. Impact on Men and Male Behavior

• [64:10+]
  • Chris and Rob discuss the lack of “pushback” from men, hypothesizing that historically, societies needed to force men to become useful via rites of passage.
  • Quote (Rob, 64:44):

    “If you leave young men to their own devices, they actually don’t ... want to be men. Men ... are very happy to be withdrawn, self interested, non contributors, lazy, selfish and so forth.”

  • Modern culture's lack of affirmative manhood rituals or positive masculine encouragement leads to greater male withdrawal.

10. The Swag Gap and Failure of Cross-Sex Mind Reading

• [67:51+]
  • Chris introduces “swag gap relationships” — a meme in which women lament their boyfriends’ lack of style compared to them.
  • Rob critiques the framing, suggesting men’s attractiveness is less bound to appearance than women’s, and points out the historical gendered double standard.
  • Both speculate that as women’s earning power increases and men’s financial status declines, men may resort to more beautification.
  • Quote (Rob, 73:47):

    “...the equivalent of a swag gap would essentially be ... a woman who doesn’t work. The unspoken message ... I’m so beautiful I don’t have to participate in the rat race.”

11. Political Connotations and Social Betrayal (“Cringe is Republican Now”)

• [79:29+]

  • The “boyfriend cringe” phenomenon is so strong it’s even linked to right-wing politics or “betraying the cause” (e.g., Taylor Swift, Adele losing weight).
  • Quote (Chris, 82:19):

    “That’s like saying Usain Bolt should cut off his legs in solidarity with the disabled community.”

• Rob and Chris note the performative solidarity in progressive spaces rarely extends to real-world personal sacrifice.

Notable Quotes & Timestamps

• Rob Henderson [04:08]:

  “Luxury beliefs are ideas and opinions that confer status on the affluent while inflicting costs on the less fortunate.”

• Chris Williamson [07:59]:

  “Most relationships now are more brand collaborations than they are meaningful connections.”

• Chris Williamson [16:01]:

  “If you can’t get what you want, you must teach yourself to want what you can get.”

• Rob Henderson [23:34]:

  “If you can’t get something, you train yourself to not want it, or you teach yourself that this is undesirable.”

• Rob Henderson [34:52]:

  “...elite women, high status women, say this is what a successful family looks like and you need to be able to afford all of this...”

• Chris Williamson [36:58]:

  “Very rarely are we aware of what the ultimate reasons for our behavior are ... you are much more effective at deceiving other people if you also are deceived by the motivation...”

• Rob Henderson [47:47]:

  “How many articles online are here are things to avoid, not here are things to chase?”

• Rob Henderson [64:44]:

  “If you leave young men to their own devices, they actually don’t ... want to be men.”

• Rob Henderson [73:47]:

  “...the equivalent of a swag gap would essentially be ... a woman who doesn’t work. The unspoken message ... I’m so beautiful I don’t have to participate in the rat race.”

• Chris Williamson [82:19]:

  “That’s like saying Usain Bolt should cut off his legs in solidarity with the disabled community.”

Memorable Moments

• Chris’s impromptu comedy bit on progressive solidarity and “cutting hair after a breakup” as inadvertent mating strategy sabotage. [36:58+]
• Rob’s recall of an actual magazine editor admitting certain narratives (women returning to traditional lifestyles and finding happiness) are categorically forbidden — not “clickable.” [51:22]
• The discussion of body positivity as a “scam” disintegrating under widespread use of GLP-1 drugs and Ozempic. [83:31+]
• Chris’s self-aware observation:

  “I can’t work out if this is TikTok brain slop or a genuine insight into important mating trends that will literally shape the future of humanity.” [86:06]

Final Thoughts & Takeaways

• The narrative that “having a boyfriend is cringe” is more than just an internet meme; it’s a complex social signal woven out of status, solidarity, and subtle competition—reinforced and shaped by the affordances of digital life.
• Elite discourse and performative solidarity often mask self-interested reproductive and status strategies, to the detriment of less privileged women.
• The double standards and ultimate vs. proximate motivations in both male and female behavior are deeply rooted and often invisible to those enacting them.
• The psychological consequences for both men and women are profound: men withdraw in the absence of social incentive and rituals, while women are caught between competing pressures of self-branding, genuine connection, and solidarity performance.
• The culture war over relationships is not just about dating preferences, but about the fundamental architecture of happiness, mating, and status in the modern world.

For more, check out Rob Henderson’s Substack and his memoir "Troubled: A Memoir of Foster Care, Family, and Social Class." (Released in paperback).