Cindy Crawford Reveals How Her Double Date Nights with George Clooney Have Evolved Over the Years (Exclusive)
- - Cindy Crawford Reveals How Her Double Date Nights with George Clooney Have Evolved Over the Years (Exclusive)
Toria Sheffield, Abby SternJanuary 10, 2026 at 7:01 PM
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From left: George Clooney, Amal Clooney, Cindy Crawford and Rande Gerber in 2022 -
Cindy Crawford revealed how double date nights with George Clooney have evolved over the years
George is a longtime friend and business partner of Crawford’s husband, Rande Gerber
The supermodel caught up with PEOPLE at the 2026 WWD Style Awards in Santa Monica, Calif., on Friday, Jan. 9
Cindy Crawford is reflecting on how her double date nights with George Clooney have evolved over the years.
Crawford, 59, spoke exclusively with PEOPLE at the 2026 WWD Style Awards in Santa Monica, Calif., on Friday, Jan. 9. The supermodel, who is married to Rande Gerber — one of George's closest friends — dished on how their couples' dynamic has changed since George met his wife, Amal Clooney.
“When I first met George, he was like the forever bachelor, right?” she told PEOPLE.
Christopher Polk/WWD via Getty
George Clooney and Cindy Crawford at the 2026 WWD Style Awards in Santa Monica, Calif., on Jan. 9
“He was never getting married. And then when he met Amal and realized she was the one, then all of a sudden they're talking about kids. And so it's been fun seeing [that] ... He just took a little longer than the rest of us, but now he's fully dad and husband. He's great,” she added.
George, 64, and Rande, 63, have been friends for decades, and founded Casamigos Tequila together in 2013 along with real-estate developer Mike Meldman. They famously sold the brand in 2017 for $1 billion and have remained publicly involved in the marketing.
Kevin Mazur/Getty
From left: Cindy Crawford, Rande Gerber, George Clooney and Amal Clooney in 2018
George met Amal, 47, a renowned human rights attorney, in 2013 after being introduced by a mutual friend.
“It's the wildest thing. A mutual friend of ours said, 'I'm stopping by and can I bring my friend?' And I was like, 'Of course,’ “ George said while recalling their first meeting when appearing on My Next Guest Needs No Introduction with David Letterman in 2018.
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“I got a call from my agent who said, 'I met this woman who's coming to your house who you're gonna marry.' The funniest thing was my mom and dad were visiting, so my parents were there, and we just talked and we stayed up all night talking,” he added.
The pair tied the knot in Italy the following year in September 2014.
Karwai Tang/WireImage
George and Amal Clooney at the BFI London Film Festival in London on Oct. 10, 2025
Following the wedding, George got candid about how his life changed when he met and married Amal.
"All I know is that it sort of changed everything in terms of what I thought my future — my personal future — was going to be,” he told PEOPLE in 2015. “But I've always been an optimist about the world. I wasn't always completely optimistic about how it was going to work out personally for me. But now I am.”
The pair welcomed twins Alexander and Ella in June 2017.
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In a February interview with The New York Times, George admitted that he had never thought much about parenthood before meeting Amal.
"[I wasn’t] in the market for being a dad … then I met Amal, and we fell in love. I have to say that, after that, everything made sense," he said.
on People
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