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Engaged at 16 and three divorces: A complete timeline of Drew Barrymore's relationships.

Drew Barrymore is a busy woman: She's an actress, a talk-show host, mother, business owner and creator of our favourite beauty content on the internet.

So basically, she's got no time for dating.

In a chat with Jane Fonda on her new talk show, The Drew Barrymore Show, Barrymore, 45, said she could relate to the 82-year-old Oscar winner, who has "sworn off men."

Growing up with Drew Barrymore. Post continues below video.


Video via Mamamia.

"Recently you said that you were swearing off men," Barrymore said to Fonda. "Can I please talk to you about this? Because I think I'm there and have been there for the last five years. Why am I here, why are you here, what's happening?"

Fonda said Barrymore was too young to be swearing off anything, saying she'd realised her life was fulfilling enough without a romantic relationship.

"Who has time?" she said, which Barrymore passionately agreed with.

"Yes, this is where I've been at," she said. 

"I'm not closed for business but I have been in exactly that mentality for the last five years thinking, I just don't have the bandwith, I just can't fit it in."

"Well, you can squeeze a little affair or two in there. I'm all for it," Fonda responded.

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Barrymore has been single since her divorce from her third husband Will Kopelman in 2016. Together, they co-parent their two daughters, seven-year-old Olive and six-year-old Frankie.

The former child star's first public relationship was in 1989, confirmed when a 14-year-old Barrymore attended the Oscars with then-boyfriend Corey Feldman

Barrymore and Feldman at the 1989 Academy Awards. Image: Getty.

By 1991, Barrymore, then 16, was engaged to boyfriend Leland Hayward, namesake and grandson of Hollywood producer Leland Hayward. The engagement was called off after a few months.

The following year she got engaged to actor Jamie Walters. Walters photographed her nude or the cover of the July issue of Interview magazine; she also appeared nude in pictures inside the issue, despite being only 17. Their engagement ended in November 1993.

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Barrymore met her first husband, Welsh-born LA bar owner Jeremy Thomas, in early 1994. She was 19 and he was 31 when they called a 24-hour minister to marry them at 5.30am, after a friend of Thomas' joked about it.

The marriage swiftly ended - after only 19 days, according to Radar Online.

"I realised my mistake on the day I married him," Barrymore has said of the relationship.

After her divorce, Barrymore was introduced to Hole guitarist Eric Erlandson by her then best friend Courtney Love, and the pair dated for about a year from 1995-1996.

Barrymore then briefly dated Edward Norton before falling for her Home Fries co-star Luke Wilson. 

Barrymore and Wilson Image: Getty.

"From the moment I saw him, I realised he was the most incredible person I’d ever been so fortunate to meet," she told People magazine in 1998.

They dated for about two years, breaking up just before they were set to star alongside each other in Charlie's Angels, which Barrymore also produced.

It was on the set of Angels where she met her next love: comedian Tom Green.

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Throughout their relationship, the pair were known for their pranks, including one on Saturday Night Live where they pretended they were about to get married, before Barrymore left him at the altar.

Image: Getty.

In early 2000, Green was diagnosed with testicular cancer and in his book Hollywood Causes Cancer, he shared; "we lived together for a year before we were engaged, and we were engaged for a year before we got married."

They married in March 2001 and Green filed for divorce in December that same year, citing "irreconcilable differences".

In 2017, Green described the marriage as "part of that sort of crazy, whirlwind of a time," confirming he hadn't spoken to his ex for "many, many years" and was "really happy that she's doing good."

The following year he said their relationship went through a lot of pressure.

"I was probably new to show business... I'd just gone through cancer as well - I had testicular cancer - so it was just probably a lot of stresses."

Barrymore went on to have an 11-month relationship with her Confessions of a Dangerous Mind co-star Sam Rockwell, before a five-year relationship with The Strokes drummer Fabrizio Moretti.

In 2003 she stated she was bisexual in an issue of Contact.

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"Do I like women sexually? Yeah, I do. Totally. I have always considered myself bisexual. I love a woman's body. I think a woman and a woman together are beautiful, just as a man and a woman together are beautiful," she told the magazine.

"Being with a woman is like exploring your own body, but through someone else. When I was younger I used to go with lots of women. Totally - I love it."

In March 2007, former magazine editor Jane Pratt shared on her SiriusXM Satellite Radio show that she had an affair with Barrymore. 

Image: Getty.

In August 2007 Barrymore began dating actor Justin Long, who she starred with in Going the Distance and He's Just Not That Into You.

Despite breaking up in 2010, the exes are still on good terms, according to a 2018 interview by Long.

"We are in touch. I love Drew," he told US Weekly.

In March 2020, Paper Magazine posted a series of pictures of Long on Instagram with the caption: "Might get fired for this but. F**k it. Justin Long appreciation post." 






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Soon after, Barrymore commented: "Your [sic] not wrong! He's great."

Long replied: "Ah what do YOU know?!"

In 2011, Barrymore began dating her longtime friend, actor and art consultant Will Kopelman. They got engaged in December 2011 and married in California six months later.

Barrymore was pregnant with their eldest daughter Olive at the time.

They went on to have another daughter, Frankie, in 2015.

A pregnant Barrymore with Kopelman in 2013. Image: Getty.

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"Honestly, I don’t know how it is for other couples but really I like watching him be a father," Barrymore told People following Frankie's birth. 

"I know everyone says you're supposed to put your coupledom first. But I really love it being all about the kids. Maybe that's my compensating for not having parents myself or a childhood but right now, the focus is about how we’re figuring things out as parents."

Barrymore, who has been acting since she was a baby and grew up in Hollywood, surrounded by drugs, alcohol and a complicated family life, wanted to give her daughters a different kind of childhood. 

"I so wanted to raise kids in this ultra-traditional way and do everything so the polar opposite of my experience. You can talk until you’re blue in the face, but kids watch what you do every single day of your life, all day long, and that behaviour and that example and that love and community and honesty is what's making everything feel safe for my kids," she said during an appearance on The Ellen DeGeneres Show in February 2017.

She and Kopelman announced their plans to divorce in April 2016 after nearly four years of marriage.

Image: Getty.

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"Divorce might make one feel like a failure, but eventually you start to find grace in the idea that life goes on," their statement said.

"Our children are our universe, and we look forward to living the rest of our lives with them as the first priority."

At first, Barrymore said she struggled to come to terms with the divorce.

"I put in my statement about divorce the word 'failure' because it's so honest," Barrymore explained on Chelsea Handler's Netflix talk show a month later.

"Like, when you get divorced, you break up with somebody and you're like, 'Yeah, that didn't work,' and you get divorced, [but] when you get divorced you're like, 'I'm the biggest failure. This is the biggest failure.' It's so shameful and hard to actually go through that, even privately," she said.

"It's a tough time. It’s a hard thing to go through. It's like you’re being put on a cheese grater and every second, going, 'Ah! This wasn't the plan!'"

Since their split, Barrymore and Kopelman have maintained a close relationship and co-parent their daughters, who they mostly keep off social media and out of the public eye.

Barrymore and Frankie in 2017. Image: Getty.

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In December 2017, Barrymore wrote about co-parenting in an Instagram post, writing that she "would do it all over again" if given the chance.

"Will and I continue to marvel at what we made and try to be the best co-parents we can be. It's not always easy and the point is... nothing in life is. But it doesn't mean that any bitter outweighs the sweet!"

In 2018, Barrymore told Entertainment Tonight she'd given dating apps a go, but it didn't work out.

"I got off [dating apps]. It was fun to try though. I've been working out there in the public since I was young so that myth of the blind date eluded me and I always wanted to do it so that was like a dating app for me," Barrymore explained.

"But then it's not blind on my side so it just, I don't know, doesn't work."

Earlier in 2020 Barrymore told People she is a "hopeless romantic", but she'd never marry again.

"Everybody on this planet needs love in some form," she said. "And we are constantly contending with relationships. Love and those relationships may look differently for people. But it’s there at its core. So, I can’t help but want to explore and examine that," she said.

"And I also believe people should not say the word 'never,' and I will never, with a capital N-E-V-E-R, never get married."

She said divorce was different to a standard breakup. 

"I never want to be entwined with someone like that again ever.

"You break up, and you move on. You get divorced, and it's just so different. I love that we are trying to hold on to an institution that [started] when the closest person to you for companionship was a three-day horse ride away and your life span was 30 years.

"It doesn’t mean that maybe I wouldn’t like to meet someone, especially when my kids go off to college," she says. "Or a year from now, I could be totally in love. I’m open to it; I’m not seeking it. My cup runneth over. I have so much love in my life."

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Feature image: Getty.

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