Models Christie Brinkley and Sailor Brinkley Cook. Picture: Frazer Harrison/Getty Images for NYFW: The Shows
Christie Brinkley and Daughter Sailor Matched with Same Men on Dating App – Despite a 44-Year Age Gap
The dating world can be unpredictable — and sometimes, even a little shocking. But what happens when a mother and daughter unknowingly attract the same men on a dating app?
That’s exactly what happened to 71-year-old supermodel Christie Brinkley and her 27-year-old daughter Sailor Brinkley Cook, proving that age may be just a number — at least in the swipe-right world of online dating.
The surprising (and slightly awkward) revelation came out during Brinkley’s recent appearance on the “Are You A Charlotte?” podcast, hosted by Sex and the City star Kristin Davis.
A Dating App Experiment Gone Viral
While discussing the complexities of dating as an older woman, Davis brought up the frustrating double standard — especially for women over 50.
“There’s such an extreme dichotomy,” Davis explained. “Men won’t date women their own age, even when those women are beautiful and accomplished.”
That’s when Christie dropped a bombshell.
She shared that Sailor had once secretly put her on a dating app — as part of a mischievous social experiment — just to see what kind of men would show interest in her iconic mom.
“She put me up there without telling me,” Christie said, laughing. “And then she said, ‘Mum, you’re right not to go on it, because the same guys that said yes to me, are saying yes to you.’”
Cue the shock, amusement, and disbelief from listeners — including Davis, who was floored by the unexpected twist.
“Wow! That’s a really fascinating little experiment,” Davis exclaimed.
Age, Beauty & Algorithms: The Online Dating Paradox
Brinkley’s story has reignited a conversation around ageism in dating, especially when it comes to how older women are perceived by younger men — and how dating apps flatten age differences with a swipe.
While it's not shocking that a timeless beauty like Christie Brinkley would attract interest, what caught everyone off guard was the fact that the same men were swiping right on both her and her daughter — without hesitation.
It raises the question: Are dating app users truly interested in connection, or just driven by looks and curiosity?
Christie, who currently isn’t active on any dating platforms, seemed both amused and slightly disturbed by the results of her daughter’s digital prank.
Who Is Sailor Brinkley Cook?
Sailor, Christie’s youngest child, is a model and body positivity advocate, often praised for both her resemblance to her famous mother and her openness about mental health, self-esteem, and the pressures of growing up in the spotlight.
At 27, she’s made her own mark in the industry — even competing on Dancing With the Stars and walking the runway during New York Fashion Week. Like her mother, she’s no stranger to public attention, but this mother-daughter dating overlap was a whole new level of weird.
Brinkley’s Real-Life Dating History
Christie Brinkley has had a long and very public romantic history, including four marriages:
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Francois Allaux (1973–1981)
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Billy Joel (1985–1994), with whom she shares daughter Alexa Ray Joel, now 39
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Richard Taubman (1994–1995), father of her son Jack, now 30
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Peter Cook (1996–2008), father of Sailor
Brinkley’s most tumultuous relationship was arguably with Peter Cook, a marriage that ended after allegations of infidelity.
In her memoir Uptown Girl (released in April), Christie opens up about the pain of discovering that Cook had been unfaithful — and the devastating moment a Hamptons police officer told her that her “arrogant husband” was having an affair with a much younger woman.
“When your whole world falls apart and you realize in a heartbeat you’ve suddenly become the cliché middle-aged woman whose husband is having an affair with a much (much) younger woman — what do you do?” Brinkley wrote.
The irony of that experience now contrasts sharply with her daughter’s dating app experiment — where men are still showing interest in both generations.
The Internet Reacts: Applause, Amusement, and a Few Raised Eyebrows
Since the podcast clip went viral, reactions online have ranged from pure admiration to uncomfortable laughter.
“Christie Brinkley being hotter at 71 than most of us in our 30s? Not surprised. But matching with the same guys as her daughter? Legendary,” one fan tweeted.
“Honestly, it says more about the men than it does about Christie or Sailor,” another user wrote.
Still, many people saw it as a sweet and hilarious bonding moment between mother and daughter — with Sailor playfully turning the tables on dating culture and showing that youth and beauty are not mutually exclusive.
Final Thoughts: When Dating Gets Intergenerational
This story isn’t just a quirky celebrity anecdote — it’s a reflection of the shifting norms in modern dating. With apps placing appearance and age side-by-side in a swipeable grid, it's easier than ever for lines to blur.
And in Christie Brinkley’s case? Even time can’t blur her allure.
Whether it’s a testament to her timeless beauty, Sailor’s savvy sense of humor, or the oddity of online dating, this mother-daughter moment has struck a chord — reminding us that confidence, charisma, and connection have no age limit.
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