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Drew Barrymore's Dating History, Engagements, and Marriages

Drew Barrymore is currently dating again after being single for a period, and I think we can all agree that whoever she ends up with is the luckiest person on the planet. But while Drew's been doing her for a minute (by which I mean running the most charming talk show on TV), her dating history is full of fascinating people, a few celebrities, and several engagements you definitely forgot about. Let's start from the beginning, but not before watching this for the millionth time:

Leland Hayward: 1991

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Ron Galella, Ltd.//Getty Images

Drew and Leland Hayward III (grandson of Broadway producer Leland Hayward) were briefly engaged back in the early '90s. Not much is known about their vibe, but judging from this photo it was extremely aesthetic.

David Arquette: 1991

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David confirmed on Watch What Happens Live that he and Drew dated "for a while," going on to call her "one of the sweetest, kindest people in Hollywood."

Jamie Walters: 1992

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Drew and Jamie got engaged a year after she ended it with Leland, and things were so serious that Drew got a tattoo of his name. She later told Rolling Stone, "His name is gone. It just bled. How insane is that? When my tattoo artist did it, you could definitely read it, but he said, 'Trust me.' I asked why, and he said, 'Just trust me.' A year later the name was gone and so was Jamie."

Jeremy Thomas: 1994

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Barry King//Getty Images

Drew and Jeremy married after a whirlwind romance in 1994, but it only lasted a couple weeks before Drew filed for divorce. "He needed the marriage, and I stupidly agreed to it," she explained in the same Rolling Stone interview. "We were married for six weeks, and we were only together for, like, two days of it. It was such a joke. The whole thing was a fucking lie. The press lied about it, we lied about it."

Eric Erlandson: 1994

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KMazur//Getty Images

Yep, Drew dated the guitarist from Hole! And they seemed pretty happy, with Drew telling Rolling Stone, "I love him so much. And I have a family now from Eric, too. He has such a huge, amazing family. Seven kids. I never thought I'd have a sense of family until I had my own kids. I want two: a boy and a girl. My daughter will be named Ruby Daffodil."

Luke Wilson: 1996

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After ending things with Eric, Drew dated fellow actor Luke Wilson from 1996 to 1998. They remained on super good terms—and she even hooked him up with a role in Charlie's Angels. “That’s Drew," Luke told People. "She didn’t let the personal stuff get in the way."

Tom Green: 1999

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Drew and Tom Green got together in 2000, married in 2001, and divorced after less than a year. Told told People, “Drew is a wonderful woman. I love her very much. I wish our marriage could have worked out. I wish her much happiness.”

Fabrizio Moretti: 2002

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James Devaney//Getty Images

Drew started dating The Strokes drummer in 2002, and they were together for a pretty long time before splitting up in 2007. But Drew seems to have good memories of their time together, saying the most romantic thing anyone's ever done for her was when Fabrizio taught her to play drums:

"I had to play Meg White in The White Stripes with Jimmy Fallon on 'Saturday Night Live.' I happened to be dating this drummer for several years, Fabrizio Moretti of The Strokes. And so he taught me how to play the famous song and do the beat. He taught me all week long in anticipation of the show. That, I thought was really romantic, to get to learn a skill set that I didn't really have."

Justin Long: 2007

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Kevin Mazur//Getty Images

Drew and Justin dated on and off for several years and remain good friends. In fact, she recently had Kate Bosworth on her show and said, "My very dear old friend Justin Long — a boyfriend, a dear friend—and he and Kate have found each other in this world. [You've] become this incredibly joyous, bonded, real deal; you holding hands, ultimate couple you root for. Period."

Will Kopelman: 2011

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Donato Sardella//Getty Images

Drew and Will Kopelman started dating in 2011 and got married a year later, going on to have two sweet daughters. They ended up splitting in 2016 but have a solid coparenting relationship. Drew also recently said that she loves Will's new spouse, explaining, "He just got remarried actually last week to this most amazing woman," Drew said in 2021. "This incredible woman Allie, and I just feel like I won the lottery with her, like, I really did. I feel like I'm lucky that there's this new beautiful soul that came into our lives."

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