Drew Barrymore just revealed some shocking news about her ex-boyfriend, Luke Wilson.

Speaking to fellow actress Kate Hudson on The Drew Barrymore Show, the Charlie’s Angels actress admitted that she and Wilson were in an open relationship in the 1990s.

On the Thursday night episode of her talk show, Barrymore recalled her first meeting with Wilson, saying:

“When we first met, we were young and wild.”

Hudson, a longtime friend of Barrymore’s, added details to the story, telling the audience that they had all met together at the Chez Jay’s restaurant in Santa Monica.

“I was dating him, but I think he was also dating other people. It was an open relationship. We were young,” Barrymore said.

Hudson, who had an on-again-off-again relationship with Owen Wilson, piped up with “I’ve been there with a Wilson too!”

Although all four of them have moved on in the years since then, fans were excited to hear the details of the romantic exploits of some of the biggest Hollywood stars of the 90s.

Who Is Luke Wilson?

While many people know Wilson as Emmett Richmond, the sweet junior partner of one of Elle Woods’ law professors in Legally Blonde, Wilson has quite the prolific career in film behind him.

The youngest of the three Wilson brothers, Luke Wilson developed an interest in acting while studying in Los Angeles.

His career began when he was cast in the lead role of a short film titled Bottle Rocket in 1994, written by his brother Owen and future frequent collaborator Wes Anderson.

The short film was expanded into a feature-length movie in 1996, with the brothers reprising their roles. Although the film failed at the box office, it brought Anderson widespread attention, and famed director Martin Scorsese has named it one of his favorites.

After the Wilson brothers moved to Hollywood, Luke was cast in Telling Lies in America, and even had a cameo in Scream 2.

Wanting to expand his skill set, and avoid typecasting, Wilson agreed to star in the romantic comedy Best Men, opposite Drew Barrymore – one of Hollywood’s most sought-after leading actresses of the decade.

He reunited with Anderson for Rushmore, playing the boyfriend of schoolteacher Rosemary Cross.

In a profile in The Washington Post, Wilson is described as “forever the baby bro”, being seen as a step below his older brothers on and off the screen.

By the early 2000s, he was known as the sweet but befuddled boyfriend in many romantic comedies of the era and was on the hunt for a role that would break him out of that stereotype.

His appearance in Anderson’s The Royal Tenenbaums was a turning point for Wilson, who was able to display impeccable comedic timing and heartfelt moments within the confines of Anderson’s tight script.

Director Ivan Reitman sang Wilson’s praises, saying:

“I always had the sense that he’s an underutilized, unvalued resource. I think it’s just by virtue of his good looks that he’s gotten to be ‘the guy’ in a lot of chick movies, where he’s the kind of straight guy to the colorful, kooky girl that’s in the movie. I wanted to give him the opportunity to rock a little more in a comedy. He’s the real deal, he’s certainly as funny as his brother Owen. His comedy chops really are born of the same DNA.”

His Working Relationship With Wes Anderson 

After the twentieth anniversary of The Royal Tenenbaums, Wilson spoke about his relationship with Anderson over the years, saying he was always excited to reunite after their partnership took a series of hiatuses.

Wilson also has ideas about their next project together, telling The Playlist:

“We’ve talked over the years about the possibility of maybe doing a western with the old group. So, that would be really incredible. And I’d be just like anybody else – just to see Wes’ take on a Western would be incredible.”

He and Owen have also been in the process of writing and developing a biopic about the Wright Brothers, hoping to get that project off the ground in the near future.

Luke Wilson, Ever The Bachelor

Wilson is known as one of Hollywood’s most iconic bachelors, and fans are wondering if the star has any plans to settle down.

Recently, Wilson expressed his desire to be a father after being the fun uncle to Andrew and Owen’s children over the years.

In an interview with Hollywood Life, Wilson stated:

“I definitely want to start a family. I love my niece and my nephews. And I know how much my dad loved being a father, that was one  of the things that made him happy the most, so yeah, I’m 47, I’m ready for that. I need to get to work.”

Although Wilson may want kids, he has not had a serious relationship since 2014.

While his relationship with Barrymore was allegedly more relaxed than it seemed, it was significant in the media’s eyes at the time.

The pair were together from 1997 to 1999, when they announced their friendly split.

Both proved there was no animosity between them, with Barrymore pushing producers to cast Wilson alongside her, Charlize Theron, and Lucy Liu in Charlie’s Angels the year after their breakup.

All these years later, it seems as though Barrymore will never harbor any ill-will towards her ex, telling Hudson:

“We’re just young. We’re having fun. We’re all playing, acting, hanging out,” she recalled. “You’re not taking it all so seriously, and it was fun, and we had the best time.”

He then dated Gwenyth Paltrow for around a year and later joked to Conan O’Brien that he had a tendency to fall for his female costars in every project.

As far as the world knows, Wilson’s longest relationship was with former American basketball player Meg Simpson. 

The two were together from 2008 until 2014, making this six-year relationship Wilson’s most significant since Barrymore.

Wilson, who turned 50 last September, has admitted he is beginning to be worried about his age, telling People:

“Thirty didn’t matter to me. Forty didn’t matter to me.I just steamrolled right through it, but 50. I don’t know if it’s getting to me because I am sore when I wake up in the middle of the night, and I am forgetting the names of people I know.”

“I’m definitely starting to feel panicky about some stuff,” he added.