For Cindy Crawford and her husband Rande Gerber, double date nights with George and Amal Clooney have been a decades-long tradition. From tequila tastings to red carpets and family vacations, they have one of the most enduring friendships.
The supermodel, 59, spoke with People at the 2026 WWD Style Awards. Married to businessman Rande Gerber, one of George Clooney’s closest friends, Crawford reflected on the evolution of their couple’s dynamic, especially after George met his wife, Amal Clooney.
“When I first met George, he was like the forever bachelor, right?” Crawford said. “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.”
George, 64, and Rande, 63, go way back. The pair first met at the Paramount Hotel’s Whiskey lounge in the mid-1990s. “George was shooting a movie there, and came into one of my places, and walked up to the bar. We both had a tequila together, and kind of became friends right there. Like many great stories, ours started over tequila! And the rest is history, as they say,” Rande later recalled.
Their friendship eventually turned into a business partnership when they launched Casamigos Tequila in 2013 alongside real estate developer Mike Meldman. The brand, originally a private indulgence at parties, became a billion-dollar success when it was sold in 2017, though George and Rande remain involved in the marketing.
Along the way, their social circle grew into one of Hollywood’s most famous squads. “It was just for us,” Rande told CNBC in 2017. “We didn’t really want to be in the business. We figured, George is an actor and a director. I own restaurants and bars and wasn’t looking to get into another business.”
The tequila connection also helped cement relationships between their families. Cindy and Amal, in particular, became close friends. “I think one of the things I love about Amal is that she’s not only interesting, she’s very interesting to talk to, but she’s also interested in your world as well,” Crawford once told the publication.
Her teenage children, Presley and Kaia, also found it easy to connect with Amal. Rande praised their bond as “compatible: both strong, intelligent, committed women.”
Vacationing together became a tradition over the years. In 2002, the group traveled to Italy, where George fell in love with Lake Como and eventually purchased his $100 million lakeside villa. In 2009, George, Cindy, and Rande added a Mexican compound to the mix, complete with two houses designed by architect Ricardo Legorreta.
“We have breakfast at my house, lunch at his, dinner at ours,” Rande joked. “One big family.” George met Amal at a dinner party in 2013.
The couple tied the knot in Italy in September 2014. That three-day wedding celebration included 100 cases of Casamigos flown in from the U.S., and Rande served as George’s best man.
Parenthood followed in 2017 with twins Alexander and Ella. George admitted to The New York Times that before Amal, he 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.”
Red carpet outings continue to provide double date opportunities for the longtime friends. At the November 11, 2025 Los Angeles premiere of 'Jay Kelly,' Crawford turned heads in a navy bodycon dress that nodded to the iconic Y2K bandage style, posing alongside Rande and George.
Their connection is so enduring that George has shown his appreciation in unique ways. In 2013, he gifted $1 million to Rande as a token of their friendship and later covered the family’s taxes in 2023.