A Look Back At Drew Barrymore's Fling With Owen Wilson's Brother, Luke

Having been on the celebrity scene since she was a child, Drew Barrymore has been romantically linked to many fellow stars throughout her Hollywood career, including A-Lister beau Corey Feldman and now-married ex-boyfriend Justin Long. Back in the late '90s, the California native had a fun and fast fling with actor Luke Wilson, the younger brother of Owen Wilson.

Barrymore reflected on her relationship with Luke in a 2022 episode of "The Drew Barrymore Show" while interviewing her long-time friend Kate Hudson. As the two reminisced about their initial meeting, Barrymore remembered that she was dating Luke while he worked with Hudson on the movie "Alex and Emma." "I was dating him, but I think he was also dating other people," Barrymore revealed. "It was an open relationship; we were young."

The "50 First Dates" star goes on to describe the relationship, which lasted from 1996 to 1998, as fun and lighthearted. "It's so funny because when you're young, you're like, 'It's low stakes, we're just young,'" she said. "'We're having fun, we're all playing, actors, hanging out.' You're not taking it all so seriously, and it was fun and we had the best time."

Barrymore and Wilson met through the comedy Best Men

While Drew Barrymore reflected on her past relationship with Luke Wilson on an episode of her talk show, she also shared details about the fling in the 2003 book "Drew Barrymore: The Biography" by Lucy Ellis. Barrymore and Wilson collided while filming the 1997 comedy "Best Men," initially meeting in director Tamra Davis' kitchen.

"He was the prince around a silver refrigerator," Barrymore said. "I didn't believe in love at first sight before I had met him, I kind of had to be clobbered over the head to get it. When I looked around [the refrigerator], Luke was on the other side. That was it, and my life changed."

While Barrymore felt an instant connection to Wilson, Ellis explains that it wasn't until the end of filming neared that Wilson asked out his co-star. "It seemed natural," Wilson said. "She makes you feel at ease. She's so smart and funny and ready to laugh." Even then, the two decided to keep the details of their relationship low-key, departing from Barrymore's typical M.O. of the time.

The actors remained on good terms post-breakup

Drew Barrymore and Luke Wilson dated for roughly two years, with their relationship spanning from 1996 to 1998. During that time, the actors starred together in "Home Fries," a 1998 romantic comedy that received mixed reviews. While it's unclear why the two stars eventually called it quits, they maintained a positive relationship after their split.

In fact, Barrymore even arranged for Wilson to appear as Cameron Diaz's love interest in their 2000 flick "Charlie's Angels" after the breakup. "That's Drew," Wilson told People in 2003. "She didn't let the personal stuff get in the way." Even decades after their split, Barrymore and Wilson still appear to remain on good terms.

While their careers have taken them in different directions, the "Santa Clarita Diet" actor attempted to lightheartedly prank call the Wilson brother with Kate Hudson during a 2023 episode of "The Drew Barrymore Show." Unfortunately, she and Hudson accidentally ended up calling another Luke, who had appeared with the actor in her movie "Never Been Kissed." While this wasn't the Barrymore-Wilson reunion we had hoped for, it sure made for a fun moment.