Zendaya, Kylie Jenner, and Jennifer Aniston are all dating the same man.
Not literally, of course, but across generations and industries, these women are choosing partners who look nothing like the old alpha-Hollywood-leading-man fantasy: emotionally open rather than dominant, supportive rather than status-obsessed, and comfortable not being the loudest or most powerful person in the room.
The fact that this still confuses and irritates people tells you everything you need to know about where masculinity is right now.
That irritation was visible this week when Jim Curtis, Aniston’s partner, appeared on The Today Show.
Curtis, a hypnotherapist and transformational coach, was meant to be discussing his new book, but inevitably ended up talking about his relationship. Asked how long they had been together, he smiled, hesitated, and said it had been ‘a long time… almost close to a year’.
When the presenter teased him for blushing, Curtis laughed and agreed. It was gentle and unguarded, which may explain why it has provoked so much snark online.
As one X user put it, ‘Not Jenn Aniston dating this loser.’
Someone else put it more simply and brutally, writing ‘Major ick.’ Another wondered, ‘When she could have any man in the world, why is she with this guy???’
Since he and Aniston were first linked last summer, Curtis has been mocked online for his work in mental wellness and his evident emotional openness.
Psychotherapist and sex and relationships expert Lucy Beresford says this reaction reflects a broader shift that some people are still struggling to catch up with.
‘I see it a lot in women who are back on the dating scene or approaching their second big relationship,’ she says.
‘The old model and the old gender-stereotypical roles are shifting. Many women are welcoming men who are more nurturing and emotionally aware, partly because women themselves are much more in touch with their so-called masculine side.
‘They’re in control of their careers, their finances, their sexual and emotional fulfilment — and they’re less tolerant of old-school masculinity.’
Beresford believes the backlash against women like Aniston – who have long been seen as symbols of the ideal woman – dating less stereotypically masculine men is rooted in fear rather than taste.
‘These stereotypes evolved in the first place because they made people feel safe,’ she explains.
‘Society is changing, but it’s taking time to catch up. What Aniston is saying is, I’m still a very feminine woman, and I’m allowing myself to be loved and held by a man like this. Online, people see it very binarily, and that’s where the discomfort comes from.’
The same discomfort greeted news that Kylie Jenner was dating Timothée Chalamet. They seem like such an unlikely pair that some fans originally thought that the couple was a PR move orchestrated by Kris Jenner.
Despite his success, Chalamet’s artistic sensitivity and lack of alpha posturing left many observers scrambling to explain the pairing, especially given Jenner’s track record of dating more stereotypically masculine men like Travis Scott, with whom she shares two children.
Meanwhile, Zendaya’s relationship with Tom Holland has produced endless commentary about his openness, therapy talk, and visible emotional support — traits that are praised, but still treated as surprising and uncommon for a man.
Relationship coach Lorin Krenn sees a clear pattern.
‘When we look at recent high-profile relationships, including Aniston’s and pairings like Kylie Jenner and Timothée Chalamet, there does appear to be a genuine shift away from traditional alpha masculinity,’ she says.
‘What many women are responding to now is emotional steadiness, self-awareness and inner security. Confidence is still attractive, but it’s quieter and more grounded, rather than performative.’
Krenn argues that ridicule is a cultural lag rather than a genuine rejection. ‘Masculinity has long been shaped around emotional suppression, so men who deviate from that script challenge deeply ingrained norms. Ridicule becomes a defence mechanism. It protects outdated ideas even as many women are increasingly saying they want something different.’
Power plays a role too. ‘When women are more famous or wealthy than their partners, it still destabilises long-held hierarchies,’ Krenn says.
‘Society has been conditioned to see male status as a prerequisite for relational legitimacy. When that flips, people project insecurity, even when the relationship itself looks grounded and healthy.’
Aniston’s dating history sharpens that point. Her relationships with Brad Pitt and later Justin Theroux were relentlessly narrativised, alongside years of speculation about her body and fertility.
She has since spoken openly about IVF and the toll of decades of invasive scrutiny. Desire, after that kind of experience, tends to recalibrate.
Clinical psychologist Daniel Glazer describes the shift as structural: ‘I see this less as a fad and more as a recalibration of what feels safe and attractive,’ he says.
‘Women tell me they are drawn to partners who can manage their emotions, communicate openly, and show vulnerability. These qualities are associated with safety. But in the public sphere, emotional restriction is still rewarded, so openness attracts ridicule rather than recognition.’
Curtis and Aniston were introduced by friends, talked for months before dating, and went Instagram official with a low-key black-and-white photo. In Elle, Aniston described him as ‘very normal’ and ‘very kind.’
That normality, so often framed as underwhelming, is arguably the most radical part of the story.
The idea that Zendaya, Jenner, and Aniston are ‘dating the same man’ is shorthand, of course.
What they are really choosing is the same value set in a partner, one that includes emotional fluency, mutual respect, and a rebalancing of power. The backlash reveals how unsettled we still are by masculinity that does not insist on dominance.
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