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Dating apps these days can feel more exhausting than exciting. Gym selfies, half-baked podcast quotes, and some men whose personalities seem stuck somewhere between a viral Jordan Peterson clip and a Dubai skyline hustle meme have created a dating environment that feels performative, exhausting, and repetitive.
By 2025, many women have grown tired.
Across TikTok, group chats, and real-life dating, women are quietly finding a solution outside their own generation, or so they think: trying to date around the algorithm.
For many, the appeal of age-gap dating isn’t novelty; it’s escape.
Gen Z women are swiping up to millennial men with the belief they have “missed out on the content of the manosphere,” according to Annabelle Knight, a UK-based sex and relationship expert, The Matchmaker’s Match author, and couples coach.
She describes the shift to Indy100 as “the ‘push and ‘pull’ effect,” explaining that “some men have been pulled down the red pill path and that has ‘pushed’ women to seek meaningful relationships with men that they believe will find them equal.”
Annabelle adds that millennial men “have largely missed out on the content of the manosphere and as such are likely seen as being more emotionally available, less performative and are capable of offering a stable relationship”.
One podcast sparks debate on this trend. Cambridge HSPS finalist Tilly Middlehurst explains that “more and more Gen Z women are trying to date millennial men because they missed the ‘red pill’, manosphere stuff, so millennial men are ‘more normal’ than Gen Z men,” adding that “as a young woman [...] it’s very difficult for those women to date.”
Comments from millennial men about the episode echo the point: “When I was on the apps, I was getting tons of messages from younger women. They were impressed that I read books, cleaned my apartment, and saw them as people. The bar is in hell.”
Another writes, “As a millennial man, I'm disappointed with Gen Z men, like come on, we worked so hard to push the social progress, why do you want it to go backwards?”
The motivator is emotional authenticity
Cross-generational dating isn’t new by any means, but the reason behind it is.
After a decade of men learning about women through algorithms rather than relationships, many women are choosing partners who feel less “trained” by the feed.
Annabelle sees the trend as a response to cultural pressures rather than a fad.
“There’s been much media coverage on the spread of manosphere ideas that are shaping younger men’s behaviours,” she notes. Subsequently, women perceiving these shifts are opting out.
But Annabelle also stresses that age gaps aren’t a guaranteed shortcut to a deeper connection; they also often come with “different media habits.”
She points out that “Gen Z are the heaviest phone users in the country, clocking up hours per day on their phones,” which may clash with older partners’ norms.
She also warns that “your life timelines don’t align,” with differing ideas of “when or if to start a family” and what career progression looks like.
Financial imbalance is another sticking point. Annabelle notes that “an age gap relationship can often be heavily unevenly split, with the older of the two sometimes bringing far more to the table financially speaking.”
How social media shapes (and skews) dating
TikTok and viral content amplify the conversation around age-gap relationships and modern dating expectations.
Annabelle points to research showing that social platforms “play a massive role in shaping dating norms and identities for emerging adults.”
Trends can “lead to a black and white way of viewing the dating world,” she says, especially with phrases like “he’s giving side quest energy,” “I’m not subscribing to that,” or “it’s giving… no” dominating discourse.
And on top of that, there’s a constantly expanding glossary of dating slang we’re all supposed to keep up with.
While these trends give daters a sense of empowerment and warning, Annabelle warns that tying dating decisions to viral language can “lead to a pattern of reactive decision making” – and even “the rejection of healthy relationships before they have a chance to grow.”
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The real friction: lifestyle, communication, expectations
Dating outside your generation can feel thrillingly different, or confusingly different.
Annabelle highlights that a major issue is “the mismatched timelines they see for their individual lives.”
Expectations around starting a family, career stages, and social circles can differ sharply. Cultural references may also diverge, “leading to more challenging moments communicating.”
But she also acknowledges the upside: “You’ll both bring a different perspective on life, which could improve your relationship skills,” and broadening social networks “could be a positive.”
When it comes to emotional compatibility, she states clearly: “Each generation has its own ideas as to what the Three C’s look like: commitment, communication and conflict.”
Those differences can either complement or clash.
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Nothing new, just a modern twist on a timeless behaviour
Age-gap relationships aren’t reinventing the wheel.
Annabelle cites examples ranging from George Clooney, 64, and Amal, 47, to Cher, 79, and Alexander Edwards, 39, emphasising that “there have been age gap relationships for decades.”
She rejects the idea that this current pattern is a fleeting trend. Instead, she argues, “rather than seeing age gap relationships as a trend, I see them as a response to an individual’s wants and needs when it comes to what they’re looking for from a partner, such as emotional compatibility and personal priorities.”
In a world where algorithms shape behaviour and flatten individuality, age-gap dating isn’t a rebellion – it’s seemingly a strategy for finding something that feels human.
Humble reminder: Age isn’t a shortcut to maturity
Still, it’s worth stating the obvious: age is not a personality trait, nor a guarantee of emotional maturity.
A millennial man isn’t inherently more grounded just because he grew up before TikTok, and a younger partner isn’t automatically less emotionally developed.
Growth doesn’t arrive with a birthday – and you don’t need a thesis to confirm that men don’t suddenly “grow up” the moment they hit 30, 38, or ever.
In the end, what matters isn’t the age gap, but whether the relationship operates with empathy, accountability, and genuine emotional availability – the things no algorithm can manufacture.
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