Digital Cover celebrities© Variety via Getty Images

Drew Barrymore, 50, makes surprising dating confession following major milestone

The 50-year-old has been married three times

Faye James
Senior Editor
March 27, 2025

Drew Barrymore has had her fair share of heartbreaks, after three divorces and a bevy of disappointing dates.

The talk show host opened up about entering a new era of her love life in a personal essay in Us Weekly, sharing that her recent birthday made her realize just how much she values her independence. 

"You know how sometimes you just feel ready? Like, deep in your bones, something shifts, and you realize – you're stepping into a whole new season of life, and it actually feels right?" she opened the essay. 

"That's me. Right now. Fifty years old. And I have to say…I think I love it here." 

She added that while chasing love was exciting for a time, she began to understand how important her relationship with herself would be as she grew older. 

"Somewhere along the way, I realized the company I was forever going to keep…was my own. I started doing things for me in a way I never had before," she recounted. 

The mother of two shared how turning 50 changed her mindset© CBS via Getty Images
The mother of two explained how turning 50 changed her mindset

"I took myself out on little solo dates. I cooked for myself like I was hosting some fabulous dinner party – candles, music, the whole thing."

She continued: "I want to be the person I can rely on, laugh with and celebrate with. And if love, in any form, comes along and adds to that? Beautiful. But I refuse to believe that life starts or stops because of anyone else." 

The mother of two opened up about her disastrous experience with modern romance on The Drew Barrymore Show on Monday, admitting that she tried the celebrity dating app Raya with disappointing results. 

© Getty Images
Drew opened up about a recent disappointing dating experience

Speaking with guests Ross Matthews and Valerie Bertinelli, Drew shared that she had been on a date in March after a man asked for her number. 

"Since then, I texted him, and I was like, 'Lovely to see you again the other night.' We went back and forth twice, and then he ended with, 'Haaaaa.' And I haven't heard anything," she said. 

"It just happens. I don't know why," the 50-year-old mused. "I don't know why. I would never do that. It doesn't cross my mind to behave like that. Like, if you put a fishing pole in it, why are you not going to follow through?" 

© Corbis via Getty Images
Her second husband was comedian Tom Green

Drew has endured a turbulent love life which has played out in the press thanks to her decades-long fame.

She dated a slew of stars in the '90s, including Corey Feldman, David Arquette and Luke Wilson, and tied the knot at just 19 years old with bartender Jeremy Scott, who was 12 years her senior.

Her second marriage was to comedian Tom Green, but the couple divorced a year after their wedding. 

© Photo: Getty Images
Drew and Will share two daughters

She dated stars like Spike Jonze, Zach Braff and Justin Long, before wedding Will Kopelman in 2012. 

The pair welcomed two daughters together, Olive and Frankie, yet sadly went their separate ways in 2016. 

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