Apr 22, 2026
Tristan wasn't looking for anything out of the ordinary, just a partnership that felt fair. But after dating a 42-year-old woman with two children, the 28-year-old said he found himself drawn to that dynamic, which was different than he was used to.
"Not just me paying for things, not just going out to a bar," he told The New York Times (1).
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Think his experience is unusual? It's not.
Age-gap relationships are having a moment but instead of older men dating younger women, there's growing fascination with pairings that flip the script, particularly older women with younger men. Suddenly, the idea of a "sugar mama" isn't whispered with judgment, it's floated with curiosity.
And for some younger men, the appeal isn't just emotional, it's financial.
The rules of dating are shifting
According to the dating app Feeld, the number of men exclusively seeking older women has jumped 64% over the past two years with the trend most pronounced among men ages 18 to 25, according to The New York Times (2).
For decades, women were socialized to date up (3) — to seek older partners who could offer stability and financial security. That expectation was rooted in necessity as much as tradition. In a now-iconic 1996 interview, Cher pushed back on that idea, recalling how her mother encouraged her to marry a rich man. "Mom, I am a rich man," she replied (4) — a line that, at the time, felt defiant.
But now, American women are becoming more financially independent than ever, controlling a growing share of wealth and making more of their own financial decisions — even as gaps in pay (5) and long-term wealth persist. Between 2018 and 2023, women's wealth grew by 51%, outpacing overall global wealth growth (6). In the U.S. and Europe, women now control roughly one-third of retail financial assets, a figure projected to climb to as much as 45% by 2030, according to McKinsey & Company (7).
As financial independence grows, so does the freedom to choose partners for reasons beyond economic security and that shift is starting to reshape modern dating.
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Why dating is getting harder to afford
For young men, the pressure of affording dates is tough. The average cost of a date in the U.S. has climbed to $189 (8), according to the BMO Financial Group Real Financial Progress Index, with Americans spending more than $2,300 (9) on dating over the past year. Roughly half (10) of Gen Z and 40% of Millennials say those costs are getting in the way of their broader financial goals.
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At the same time, expectations around who pays haven't disappeared. While there's ongoing debate online about splitting the bill, traditional norms still linger. A 2019 survey by dating site Elite Singles (11), found that 63% of men and 46% of women still believe men should pay on the first date.
David Frederick (12), an associate professor of psychology at Chapman University and author of research on who pays for dates, says there's still a script many people follow. Men are often expected to pay in full, while women are expected to at least offer — whether that's reaching for their wallet or signaling a willingness to split, even if the assumption is that they won't.
"That puts a considerable financial pressure on young men aged 18 to 25 like never before," Cody Schuiteboer, CEO of Best Financial told Moneywise. "While entry-level salaries do not increase enough to cover the costs of even simple dinners and other activities associated with dating, these young men usually face extra challenges of repaying student loans and high rent."
Schuiteboer says he's seen that pressure firsthand, pointing to young men struggling to afford even basic dinners while increasingly encountering women in their 30s and 40s who are out-earning them.
"An older financially stable partner is usually emotionally mature and experienced with dating, which makes them more reasonable in their behavior related to dating costs," he explained. "For example, such a partner would rarely make unnecessary ego-based moves when discussing money and sharing the financial responsibility, which is especially appreciated by immature younger men."
As priorities shift, so do relationships
As expectations shift, so does what people actually want from a partner.
"If I were to take the finance bro out of finance, would I actually like who he is inside?," Emily Leibert, a staff writer at The Cut, said in an episode of The Opinions (13). "And I think a lot of people would say: 'Maybe not.' Sorry to the finance bros."
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Older women aren't necessarily looking for or overly concerned with someone to pay for dates. When Asha Elias began dating again after a marriage to a man 14 years older, she found herself in a different dynamic — this time as the older partner, with a boyfriend seven years younger than her.
"He cooks for me. He cleans. He looks great doing it. Sometimes, yes, he likes to rave and stay out until the sun comes up," she wrote in a Cosmopolitan article (14). "I've never been happier or felt more authentic."
People date up or down for a range of reasons that don't always come down to money. It's less about who earns more and more about how you manage it together. Setting a realistic budget for date nights, being upfront about expectations and keeping communication open can help avoid awkward money moments.
As the financial dynamics evolve, so do the reasons people pair off in the first place.
"It makes sense for them to marry people they truly love, regardless of finances. That is why this age-gap pattern appears as a natural result of economic changes in society," Schuiteboer said.
Article Sources
We rely only on vetted sources and credible third-party reporting. For details, see our ethics and guidelines.
The New York Times (1),(2),(13); BBC (3); Instagram (4); Pew Research Center (5); McKinsey & Company (6),(7); BMO Financial Group (8),(9),(10); Elite Singles (11); SAGE Journals (12); Cosmopolitan (14)
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Victoria Vesovski is a Toronto-based Staff Reporter at Moneywise, where she covers the intersection of personal finance, lifestyle and trending news. She holds an Honours Bachelor of Arts from the University of Toronto, a postgraduate certificate in Publishing from Toronto Metropolitan University and a Master’s degree in American Journalism from New York University’s Arthur L. Carter Journalism Institute. Her work has been featured in publications including Apple News, Yahoo Finance, MSN Money, Her Campus Media and The Click.
