Luke Grimes is looking back at that very awkward time he hit on Drew Barrymore and her Charlie’s Angels costar Cameron Diaz at a Hollywood bar.
The Yellowstone and Marshals actor refreshed the talk show host’s memory of the first night they met on Friday’s episode of The Drew Barrymore Show.
“You wanna hear something crazy?” Grimes asked after he took his seat in the studio. “We’ve met before.”
Luke Grimes and Drew Barrymore on ‘The Drew Barrymore Show’
Credit: The Drew Barrymore Show (2)
Barrymore, a self-described Yellowstone superfan, seemed shocked by Grimes’ revelation and quickly pressed him for details.
“This story is gonna make me sound terrible. This is, like, 20 years ago,” he prefaced. “I’d just moved to L.A., and do you remember that club Teddy’s?”
After Barrymore confirmed that she was familiar with the bar, Grimes set the scene.
Barrymore and Grimes hug it out on ‘The Drew Barrymore Show’
Credit: The Drew Barrymore Show
“You were there with Cameron Diaz, and a friend of mine was daring me to go up to women and say pickup lines,” he said, “and he dared me to come up to you two and do it.”
His flirtatious advance received mixed reviews.
“I forget what line it was, but I did, and Cameron hated it,” Grimes recalled — to which a laughing Barrymore responded, “That tracks.”
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He told Barrymore that she was much more receptive to his attempt. “You were like, ‘That’s actually pretty cute,'” Grimes said. “And you were nice about it, so thank you. You didn’t totally reject me. I just… Thank you for being nice to me.”
An overjoyed Barrymore quickly pulled Grimes into a hug before taking a moment to commend him for his bravery.
“By the way, thank you for even trying to fake a pickup line!” she exclaimed. “Because … if there’s any men out there, you can fake-pickup-line me whenever!”
While Grimes’ flirting may not have worked on Barrymore or Diaz, the actor has since found love. He married his wife, Bianca Rodrigues Grimes, in 2018, and the couple welcomed their first child together, a son named Rigel, in 2024.
Diaz is also taken after marrying Good Charlotte musician Benji Madden in 2015. The couple, who began dating in 2014, are parents to daughter Raddix and son Cardinal.
Barrymore is currently in her single era following her divorce from Will Kopelman — with whom she shares two daughters, Olive and Frankie — in 2016. The host often talks about her dating experiences on her show, from getting ghosted by a man to thinking that she was going to be killed on a first date.
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