The Truth About Drew Barrymore And Luke Wilson's Relationship

July 2024 · 4 minute read

Drew Barrymore has come a long way since her troubled past as a child addict and rebellious teen. After three failed marriages and two kids, the Never Been Kissed star has also gone on an acting hiatus as she's not interested in doing movies anymore. Now, it's not because she's done making money and is content with her current $125 million net worth. It's actually a decision she had to make to be more available to her kids. How grown-up, right?

But recently, the actress reminded us of her "young and wild" days when she interviewed her friend, How to Lose a Guy in 10 Days star Kate Hudson. There, the two talked about Hudson's previous relationship with Owen Wilson whose younger brother Luke dated Barrymore, non-exclusively. Here's everything you need to know about that unconventional affair.

RELATED: Paris And Kathy Hilton Tearfully Re-Discuss Boarding School Abuse On 'The Drew Barrymore Show'

What Drew Barrymore And Kate Hudson Revealed About Dating The Wilson Brothers

"When we first met, we were young and wild," Barrymore told Hudson during a recent episode of The Drew Barrymore Show. Hudson agreed and recalled working with Luke Wilson at that time. They were filming the 2003 film Alex & Emma. "I was dating him, I think," the talk show host said of the actor. "But I think he was also dating other people. It was an open relationship, we were young." The two laughed it off. Hudson added, "I've been there with a Wilson too."

Hudson first met her ex-boyfriend Owen Wilson while they were filming the 2006 movie You, Me & Dupree. They had an on-and-off relationship until 2008. "It's so funny because when you're young it's like, 'It's low stakes. We're just young, we're having fun, we're playing, acting, hanging out,'" Barrymore said of those times. "You're not taking it all so seriously, and it was fun and we had the best time." It makes you wonder what her relationship with the youngest Wilson brother was really like. Well, we've got all the deets.

RELATED: The Truth About Dax Shepard And Kate Hudson's Relationship

What Was Drew Barrymore And Luke Wilson's Open Relationship Really Like?

Barrymore and Wilson started dating in 1996 while shooting Best Men and Home Fries together. "From the moment I saw him, I realized he was the most incredible person I'd ever been so fortunate to meet," the actress said of the Idiocracy star. The two dated for two years. Though Barrymore described herself as "young and wild" back then, she and Wilson didn't have crazy antics on the red carpet like former 90s couple Angelina Jolie and Billy Bob Thornton. If anything, the non-monogamous couple always looked classy during major public appearances.

Wilson has never really shared details about his relationship with Barrymore. But the two seem to have kept it cool all these years. As Barrymore said, they were only having fun back then. At that time, she had also just gotten out of her 19-day marriage to Jeremy Thomas. She was only 19 when they tied the knot in March 1994. The two decided to get married after only six months of dating. Barrymore soon realized it was a mistake that she went to their honeymoon alone. "I got a phone call from her — in Hawaii! She'd gone off on our honeymoon without me," said Thomas.

RELATED: Drew Barrymore Remembers The Time Of Her Life On Keanu Reeves Motorcycle

Why Did Drew Barrymore And Luke Wilson Break Up?

The two never disclosed the reason for their split. But if we'd have to guess, the relationship probably just ran its course. They split in 1998, just right before filming Charlie's Angels together where Wilson played Cameron Diaz's love interest. It wasn't awkward, though. "That's Drew -- she didn't let the personal stuff get in the way," the actor said of his ex-girlfriend's professionalism. Barrymore also moved on pretty fast. In 1999, she started dating another co-star in the film, Tom Green.

The two also had a short-lived marriage. They got married in 2001 and divorced six months later. The two didn't speak to each other for almost two decades. It wasn't until October 2021 that the two met again. It was in an episode of Barrymore's talk show. "We have not seen each other face-to-face, actually, in almost 20 years," said the host. Green then said that it was a "good" kind of "weird" seeing her again. The actress replied, "Well, I respect and love you" to which Green said, "Love you, too."

Wilson, on the other hand, went on to date his The Royal Tenenbaums co-star Gwyneth Paltrow after his relationship with Barrymore. They dated for a year in 2002. He said he was taken by her "her goofy sense of humor." Hudson also had nice things to say about this Wilson brother, especially regarding his girlfriend choices. "He's chosen wonderful women to be with, and he doesn't hold a grudge," said the actress.

NEXT: Bill Murray Says Luke Wilson Is The Real Reason Gene Hackman Was So Awful On The Set Of 'The Royal Tenenbaums'

ncG1vNJzZmivp6x7tbTErZ%2Bippeoe6S7zGibq52nYq%2BivtGypKiqlWK5trfEZq6ipKOku26%2BxKWYraGfo8Cptc9o