Drew Barrymore's Rocky Romance History: ''Now She Feels Like She Needs to Live Her Own Life''

Engaged for the first time at 16, the actress and scion of Hollywood royalty has been in love with love forever—and yet impossible to pin down

By Natalie Finn Apr 01, 2016 11:12 PMTags
Drew Barrymore, Will Kopelman. KissingJason Kempin/Getty Images

It's best to always expect the unexpected with Drew Barrymore, and that has gone for her career and her love life.

The quirky actress, born into one of Hollywood's most storied families, has surprised at every turn. She made her acting debut at 4, co-starred in one of the biggest movies of all time (E.T.) at 6 and seemed all washed up by 21. But then she turned it all around and became one of the biggest—and most beloved—stars on the screen.

Now, at 41, she's a mother of two, a businesswoman, an author and a producer as well as an actress—though considering she had been doing that practically her entire life, she hasn't had much trouble putting movies on the back burner while she attends to her daughters, her Flower beauty line and her various other pursuits.

What it has always seemed like, where Drew is regarded, is that nothing can hold her down for long and she won't be held back by anything. And it seems as though that is the case when it comes to her relationships, too. She may just be too much of a free spirit to be attached for too long.

Gregg DeGuire/WireImage

E! News confirmed today that she and husband Will Kopelman, the father of her two girls, had split up after close to four years of marriage. A source told us that they had been living primarily apart for several months.

The once-blissful duo tied the knot June 2, 2012, at Drew's estate in Montecito, Calif., and daughter Olive was born that September. Her sister, Frankie, arrived in April 2014.

"They were good friends who blossomed into something more," another source told us Friday. "Drew felt, after dating so many guys who were wrong for her, that he would be good for her. But she kind of always had a feeling it might not be forever. Then they had kids and she stuck it out for them. Because of what she went through as a child, she didn't want to break the family up."

Barrymore's parents divorced when she was 9 and she had rocky relationships with both. Her father, John Drew Barrymore (son of legendary actor John Barrymore), died in 2004.

"Now she feels like she needs to live her own life," the source added.

Drew had indicated that her relationship with Kopelman wasn't like the ones that had come before—for better or worse.

"It was never really love at first sight," she said in the November 2015 issue of InStyle. "Will struck a lot of my pragmatic sides. He was someone who was always reachable on the phone, someone who was a classy human being, someone who had this incredible blueprint of a family that I don't have."

Drew also said, "We've made many compromises and concessions, but when it comes to how we deliver likes and dislikes, we're polar opposites. It's still really hard.''

According to a source, Barrymore and Kopelman went to marriage counseling last summer to try and work out their issues but the marriage was "broken at that point

Kevin Mazur/Getty Images for Baby Buggy

"Will and Drew are not on bad terms," the source continued. :They love each other, but in a different way, and will continue to be supportive parents. They wanted to make this process as seamless as they could for their family. 

"The kids will be spending time with both Will and Drew and they plan on making this split peaceful."

And that sounds exactly like what Barrymore, who has talked about the importance to her of being a hands-on parent, would want.

Courtesy Wildflower

The memoirist pointedly avoided rehashing her past relationships in her book Wildflower, she told the mag, because she felt it "inappropriate" to discuss such things in what she meant to be "a love letter to [her] daughters."

"They don't need to know about my sex life," she added.

And, to be frank, there coulda been some sex in that book.

Barrymore may not have found Mr. Forever along the way, but she has bravely remained in love with love throughout her life.

Ron Galella, Ltd/WireImage

Emancipated from her parents, she was first engaged at 16 to Leland Howard, a fellow old-Hollywood family scion. That didn't pan out, but then at 17 she was briefly engaged to Jamie Walters of "How Do You Talk to an Angel" and later Beverly Hills 90210 fame. (Our YM-reading memories vaguely serve when it comes to their cuteness factor.)

Barry King/Liaison

Drew married bar owner Jeremy Thomas when she was 19 but filed for divorce less than two months later.

During some time off from public relationships, she rebooted her career with a string of prominent roles in Boys on the Side, Mad Love, Batman Forever, Everybody Says I Love You, Ever After, Scream, The Wedding Singer, Ever After and Charlie's Angels.

Columbia Pictures

In 1999, it was a right odd couple alert when Barrymore started dating then-MTV host Tom Green.

Jeff Christensen/REUTERS

It may not have been love at first sight with Kopelman, but she seemed really into Green (she must have been to appear in Freddie Got Fingered). She scored him a role as her onscreen boyfriend, "The Chad," in Charlie's Angels and they married in July 2001. It was Green who filed for divorce that December.

Drew was back in the saddle the following year, though, and she dated The Strokes drummer Fabrizio Moretti for five years. In the 2005 she called the musician the "kindest, smartest, most talented person I have ever known."

KMazur/WireImage

They split up in 2007, with Us Weekly reporting that Drew had actually broken up with him twice before the final split.

She started dating Justin Long off and on for two years, meeting him on the set of He's Just Not That Into You and starring with him in the prophetic 2010 rom-com Going the Distance, but they were done for good shortly after that.

Kevin Winter/Getty Images

And it was then, in early 2011, that she started dating Kopelman, an art consultant and son of former Chanel CEO Arie Kopelman, and he had popped the question by January 2012.

"We're both very particular and detail-oriented. We love art and music and adventures, and we laugh our asses off together," Barrymore gushed about her husband in the January 2013 issue of Allure.

While we're sorry if she is that it didn't work out with Will Kopelman in the end, we can still guess that Drew won't be giving up on love anytime soon.

—Reporting by Beth Sobol