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Modern WisdomThe Rise And Fall Of The Girlboss Meme - Katherine Dee
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At a glance
WHAT IT’S REALLY ABOUT
From Girlboss Burnout To Sex Negativity: Mapping Modern Dating Culture
- Chris Williamson and writer Katherine Dee unpack the rise and fall of the ‘girlboss’ archetype, the shift from sex positivity to sex skepticism, and how internet subcultures shape modern dating expectations for both men and women.
- Dee explains how legacy media, Tumblr, and now TikTok amplified fringe ideas into mainstream discourse, fueling trends around identity, sexuality, and feminism that are now entering a more self-critical, moderate phase.
- They explore how chronically online life distorts perceptions of romance, increases “ambient rejection,” and encourages pathological dating strategies on both sides, from incel culture to girlboss oversharing and manifestation fantasies.
- The conversation closes with Dee’s blunt dating heuristics, emphasizing boundaries, predictability, shared values, and the dangers of high body counts, limerence, and trying to manipulate relationships via sex or convoluted “hacks.”
IDEAS WORTH REMEMBERING
5 ideasThe girlboss archetype burned out as its promises clashed with loneliness and aging.
What began as an empowering ideal—women ‘having it all’ in career and casual sex—devolved into a “train-wreck girlboss” trope of oversharing, manic spending, and emotional denial, which many women abandoned as it stopped serving them in their 30s.
Sex positivity has hit its limit, prompting a swing toward sex skepticism and restraint.
After years of pushing every taboo—from Teen Vogue kink pieces to extreme TikTok content—the only way to be transgressive became ideological, and many young people and mainstream feminists are now re-evaluating hookup culture, MeToo excesses, and casual sex norms.
Online life massively increases low-level rejection, which compounds into deeper hurt.
Dee’s “rejection sensitivity” idea highlights that dating apps, social media, and ghosting create thousands of micro-rejections, so when a big rejection hits, it lands on top of a huge unseen pile, making people feel far more fragile and jaded than they realize.
Most ‘new’ TikTok pathologies are old internet patterns with bigger reach.
Trends like self-diagnosed multiple personality disorder appeared on Usenet and personal sites long before TikTok; what’s changed is user volume and journalists amplifying niche behaviors for clicks, turning micro-subcultures into perceived generational crises.
Dating works best with clear boundaries, moderate availability, and predictability.
Dee’s advice stresses not being constantly available, avoiding “relationship purgatory,” valuing people who are emotionally predictable, and recognizing that convoluted dating hacks and love-bombing narratives often mask simple truths: interest, or lack of it.
WORDS WORTH SAVING
5 quotesYou can't really be a girlboss if you're completely alone, quarantined in your apartment.
— Katherine Dee
When all the taboos have become mainstream, there is nothing left to transgress other than ideological transgression.
— Chris Williamson (paraphrasing Ben Shapiro)
We're sort of swimming in this soup of rejection, and it has to have an impact on the way we feel.
— Katherine Dee
If he doesn’t want to date you, he doesn’t want to date you. Doing this is a good way to get used for your body.
— Katherine Dee
We weren’t designed to be exposed to this many people this frequently.
— Chris Williamson
High quality AI-generated summary created from speaker-labeled transcript.
