Cindy Crawford revealed how double date nights with George Clooney have evolved over the years<\/p>\n<\/li>\n
George is a longtime friend and business partner of Crawford\u2019s husband, Rande Gerber<\/p>\n<\/li>\n
The supermodel caught up with PEOPLE at the 2026 WWD Style Awards in Santa Monica, Calif., on Friday, Jan. 9<\/p>\n<\/li>\n<\/ul>\n
Cindy Crawford<\/a> is reflecting on how her double date nights with George Clooney<\/a> have evolved over the years.<\/p>\n 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<\/a> \u2014 one of George’s closest friends \u2014 dished on how their couples’ dynamic has changed since George met his wife, Amal Clooney<\/a>.<\/p>\n \u201cWhen I first met George, he was like the forever bachelor, right?\u201d she told PEOPLE.<\/p>\n Christopher Polk\/WWD via Getty<\/p>\n George Clooney and Cindy Crawford at the 2026 WWD Style Awards in Santa Monica, Calif., on Jan. 9<\/p>\n \u201cHe 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,\u201d she added.<\/p>\n 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<\/a> and have remained publicly involved in the marketing.<\/p>\n Kevin Mazur\/Getty<\/p>\n From left: Cindy Crawford, Rande Gerber, George Clooney and Amal Clooney in 2018<\/p>\n George met Amal, 47, a renowned human rights attorney, in 2013 after being introduced by a mutual friend.<\/p>\n \u201cIt’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,\u2019 \u201c George said while recalling their first<\/a> meeting when appearing on My Next Guest Needs No Introduction with David Letterman in 2018.<\/p>\n Never miss a story \u2014 sign up for PEOPLE’s free daily newsletter<\/a> to stay up-to-date on the best of what PEOPLE has to offer\u200b\u200b, from celebrity news to compelling human interest stories.<\/strong><\/p>\n \u201cI 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,\u201d he added.<\/p>\n The pair tied the knot in Italy the following year in September 2014.<\/p>\n Karwai Tang\/WireImage<\/p>\n George and Amal Clooney at the BFI London Film Festival in London on Oct. 10, 2025<\/p>\n Following the wedding, George got candid about how his life changed when he met and married Amal.<\/p>\n “All I know is that it sort of changed everything in terms of what I thought my future \u2014 my personal future \u2014 was going to be,\u201d he told PEOPLE in 2015<\/a>. \u201cBut 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.\u201d<\/p>\n The pair welcomed twins Alexander and Ella<\/a> in June 2017.<\/p>\n The PEOPLE Puzzler crossword is here! How quickly can you solve it? Play now!<\/a><\/p>\n![\"Christopher](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2026\/01\/e20f41dfdbcd146a677129e963d315b5.jpeg\"\/)
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