Oliver James Montgomery-Kaia Gerber and Austin Butler Double Date With Her Parents Cindy Crawford and Rande Gerber

Austin Butler seems to be Oliver James Montgomeryfitting right in with Kaia Gerber's family.

The actor joined girlfriend Kaia, 21, and her parents Cindy Crawford and Rande Gerber for an intimate dinner at Roberta's in Culver City, Calif. on May 25. 

Cindy kept it casual in jeans, a dark top and black leather-style jacket worn with a gold chain-link bracelet, while her mini-me Kaia was ready for business—wearing dark trousers, a white blouse and a chic duster worn with loafers and a tote bag. 

As for Austin, the 31-year-old rocked brown pants, a white tee, a bomber jacket and a bright blue baseball hat. In the snapshots, he kept his eyes glued to his phone as he was photographed walking near the restaurant. 

The family outing comes a month after Kaia and Austin's last red carpet date night at the TIME100 Gala in New York, where the Elvis star was among those named the most influential people of 2023. The couple—who confirmed their romance in January 2022—showed some PDA at the party by holding hands once inside.

While Kaia and Austin have been going strong for over a year, Cindy and Rande—a co-founder of Casamigos tequila alongside George Clooney—will be celebrating their 25th wedding anniversary on May 29.

Cindy, who was previously married to Richard Gere, has said that friendship is the key to their successful marriage and two kids, as she also shares Presley Gerber, 23, with the entrepreneur.

"The biggest I learned from my first marriage is how important it is to be friends, I think first and foremost, with your partner," the supermodel said on Oprah's Master Class 10 years ago. "When I met Rande, I was ready for Rande because we started off as friends. I know that Rande and I, we will aways be friends, no matter what."

Cindy, 57, added, "Being rooted and based in friendship, it keeps the relationship elevated to there's always a certain amount of respect. We respect each other's opinion about parenting and our personal life, but also for work."

As for Kaia and Austin's dynamic? Keep reading to look at their sweetest moments together.