Drew Barrymore is a self-described "hopeless romantic."
The actress and talk show host has been married three times and was separately engaged two other times. In 2022, she revealed she's on a dating app (and has the cutest profile pic), though she admits it took her a while to get to that point following her 2016 divorce from Will Kopelman, with whom she shares two daughters.
"I have two young girls and, like, I don't want to bring people home," she said in a January 2022 interview with CBS Mornings. "I think it would take me a very long time to meet someone and get to know them before I could even ever introduce them to my daughters."
Barrymore has been on a few dates since her divorce, and while she's open to finding love again, she's not planning on having another wedding.
"There's no reason to be [married]," she said. "I would maybe live with someone again, maybe, but I've had kids and there's no way, I will never, ever, ever, get married again."
In September 2022, the actress made headlines after saying she can go "years" without sex on her talk show. Barrymore later clarified her comments in a "very personal" blog post, explaining that she has "finally come to the epiphany that love and sex are simply not the same thing."
As for her dating life, she wrote that she is "just in a completely different place in my life and maybe in the near future I will get into a relationship … but it simply hasn't been my priority."
On Dec. 1, 2022, Barrymore shared that she had started dating again on an episode of The Drew Barrymore Show. The host spoke to guest Whoopi Goldberg about her experience, saying, "Because it had been so many years, I started to get a little worried, like I'm too good at being alone."
Here's what to know about Drew Barrymore's star-studded dating history.
Vinnie Zuffante/Michael Ochs Archives/Getty
The pair connected while filming 15 and Getting Straight, an after-school special in which they played teen patients in a recovery program, according to the Los Angeles Times. Barrymore and Feldman attended the Oscars together in March 1989, when Barrymore was 14 and Feldman was 17. They reportedly dated until April 1990.
In January 2023, Feldman appeared on The Drew Barrymore Show. The exes took a walk down memory lane — recalling their first date as preteens before becoming an official couple a few years later.
"What happened was, I got a call one day. My grandmother says, 'We got a call from Steven [Spielberg's] office, and the little girl from E.T. wants to meet you because she's got a crush on you,' " Feldman shared.
He continued: "Of course, neither of us drove because I was still living at my grandparents', and you were living with your mom. And it was so cute. I remember taking you to the movies, I remember exactly which movie theater it was. We walked across the street, and you put your little hand up for me to hold. And I held your hand, and we walked across the street."
Jim Smeal/Ron Galella Collection
Following her split from Feldman, Barrymore briefly dated Balthazar Getty, the Getty Oil heir and Lord of the Flies star. Barrymore and Getty, who were both 15 at the time, were reportedly together from April to September 1990.
Leland Hayward III
Ron Galella, Ltd./Ron Galella Collection
Barrymore dated Leland Hayward III, grandson and namesake of legendary Hollywood agent Leland Hayward, in 1991 — when she was just 16 years old to his 24. The couple were briefly engaged before calling it quits.
Years before playing siblings in the 1999 rom-com Never Been Kissed and costarring in Scream, Barrymore and David Arquette dated — though they can't seem to agree on the nature of their past relationship.
In a 2014 episode of Watch What Happens Live, Arquette said he and Barrymore dated when they were "very young kids," adding, "She's just one of the sweetest, kindest people in Hollywood. She always has been, and she always will be. She's just a lovely, sweet person. We used to run around and just be silly."
The pair were indeed photographed holding hands in December 1991, but Barrymore denied dating Arquette in an interview with Howard Stern. Still, in March 2018, Arquette insisted to PeopleTV's Couch Surfing that he and Barrymore were once, in fact, an item.
"We also dated, but she denied it on Howard Stern," he said. "But, we dated, Drew!"
Not long after her (alleged) split from Arquette, Barrymore was briefly linked to producer, actor and screenwriter Corin Nemec in 1992. The pair attended the premiere of the film Radio Flyer together that February, but their romance appears to have been short-lived.
Ron Galella, Ltd/Ron Galella Collection
Barrymore started dating actor and musician James "Jamie" Walters in March 1992, and they got engaged that June. She was 17 years old and he was 23. They got tattoos of each others' names, but the pair broke up in in 1993 before ever walking down the aisle.
Barrymore, then 19, met 31-year-old Jeremy Thomas in 1993 at an L.A. bar he owned.
After dating for just six weeks, they married on March 20, 1994. "Usually people live together first and then get married," Barrymore told PEOPLE after their wedding. "I guess we're doing it the old-fashioned way. Kind of."
The relationship ended almost as quickly as it began: The couple split just 19 days after tying the knot. Their divorce was finalized in 1995; Barrymore cheekily referred to Thomas as "the devil" in an interview with Rolling Stone published that June.
Barrymore met musician Eric Erlandson (then a member of Hole with Barrymore's pal Courtney Love) in a dark moment. According to Rolling Stone, she was purging outside of an L.A. nightclub in June 1994 when Erlandson found her, put his hand on her shoulder and stood by to keep her safe. Two weeks later, she accidentally knocked on his hotel room door after a photographer gave her the wrong room number. It wasn't until she ran into Erlandson in Seattle, where she was shooting the movie Mad Love, that sparks finally flew. The pair quickly moved in together.
"I love him so much. And I have a family now from Eric, too," she told the outlet. "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."
Barrymore and Erlandson split in 1996, though details surrounding the breakup are scant. Erlandson hasn't spoken publicly about his relationship with Barrymore, but did reflect on the notoriety that came with it in an interview with L.A. Weekly.
"I have a negative view of it — being worshiped too much. Fame is fame," Erlandson said.
Ron Galella/Ron Galella Collection
Luke Wilson and Barrymore dated from 1996 to 1998. "From the moment I saw him, I realized he was the most incredible person I'd ever been so fortunate to meet," Barrymore told PEOPLE of her handsome Home Fries costar in 1998. After their breakup, the pair remained friendly, with Wilson even appearing in Charlie's Angels with Barrymore in 2000 as Cameron Diaz's love interest. In 2003, he told PEOPLE, "That's Drew — she didn't let the personal stuff get in the way."
During her romance with Wilson, Barrymore first connected with Kate Hudson, who was dating Luke's brother Owen Wilson. In 2022, Barrymore and Hudson concurred that neither of their relationships were serious.
"When we first met, we were young and wild," Barrymore said on her talk show of meeting Hudson. "I was dating [Luke], but I think he was also dating other people. It was an open relationship; we were young."
Barrymore added that she looks back fondly at that time in her life. "We're just young, we're having fun, we're all playing, acting, hanging out," she said. "You're not taking it all so seriously, and it was fun and we had the best time."
Barrymore and comedian Tom Green began dating in March 2000 after meeting on the set of Charlie's Angels and threw a surprise wedding on July 7, 2001, in Malibu, California. Before the couple called it quits, their marriage weathered a series of challenges, including Green's testicular cancer diagnosis and a house fire.
In December 2001, Green filed for divorce from Barrymore. "Drew is a wonderful woman," Green said in a statement. "I love her very much. I wish our marriage could have worked out. I wish her much happiness."
Barrymore later told Howard Stern of the split, "[We] were young and kind of idiots … I didn't know how to manage myself. I've always said I was a woman in the boardroom and a child in the bedroom. I could go into a studio and pitch … but I didn't know how to handle things in my personal life."
In September 2020, Barrymore and Green reunited on her talk show, and she reflected warmly on their brief marriage and one particular moment with his family.
"I've had two nights of great sleep in my life before my daughters were born. I don't know why but sleep has been a weird thing for me," she told Green. "I remember this night just being so content. I was at your parents' lake house, and I remember hearing all their voices upstairs. I was by myself and going to sleep and I was like, 'Yeah, this is what safety and contentedness feels like before you're going to sleep.' I love your parents, and I really love you and I celebrate you."
The pair reconnected in person a year later on Barrymore's show, exchanging heartfelt sentiments — but remaining platonic.
Barrymore's relationship with Fabrizio Moretti, drummer for The Strokes, was her longest at that point in her life. The couple began dating in 2002 after meeting backstage at a music festival, and they were together for five years.
In 2004, she told PEOPLE that her romance with Moretti was "the most positive relationship" she had ever been in. "Right now I'm in a phase of 'I'm not even your girlfriend. I'm your best friend who is madly in love with you,' " she told Harper's Bazaar in 2007. As the issue went to print, however, the pair split.
Still, Barrymore looks back on her time with Moretti fondly and said he did one of the most romantic things for her: teaching her to play the White Stripes' hit "Seven Nation Army" before she played drummer Meg White in a Saturday Night Live sketch. In 2009, she told W magazine that her and Moretti's past love was "one of the most, if not the most, important relationships" she'd had in her life, adding, "We're still very close."
Spike Jonze and Zach Braff
Francois Durand/Getty ; Dimitrios Kambouris/WireImage
Barrymore and Braff were spotted canoodling in New York City in February 2007, when they got close at an SNL afterparty, then again on June 30, 2007, when they kissed while out dancing (and appeared "blissful," according to an eyewitness) and went for a romantic stroll through SoHo.
One week later, Barrymore and Jonze were spotted smooching in the VIP section of a Klaxons concert in L.A. Jonze and Barrymore were first linked in March 2007.
During an interview with Oprah Winfrey in 2008, Long spoke about his relationship with Barrymore. "She's beautiful and funny," he said. "She's the most compassionate person I've ever met … She smells great." Barrymore told Winfrey, "This relationship is great. It's healthy, it's productive and it's supportive. It's full of humor and a lot of fun. I found a best friend."
After two years of on-again-off-again "chaos," Barrymore and Long split in 2010, but always remained friendly. In 2022, Long, who began dating actress Kate Bosworth in March, appeared on Barrymore's talk show. The pair reminisced on their past "hedonistic" romance and how much they've grown up in the 12 years since.
"We laughed so much, like that was so much a part of our connection was that we love funny people. We enjoy laughing at all times," Long said. "I love that we maintained our love because I know for my end it will never go away."
A tearful Barrymore replied, "I feel like we've been through so much together too. I feel like when we used to, like, talk and FaceTime, I was always like, 'You know, I've really grown up, Justin.' I always wanted to prove what a different person I was than when we dated."
Long, smiling, told her, "You were the best."
Barrymore's longest relationship was with her third husband, art consultant Will Kopelman. The couple were first linked in January 2011, got engaged in January 2012 and married in June. On Sept. 26, 2012, the couple welcomed their first child, Olive Barrymore Kopelman. Daughter Frankie Barrymore Kopelman was born on April 22, 2014.
Barrymore has said she and Kopelman were "polar opposites," something he alluded to as well. "Sometimes whom you least expect is the person you fall for," Kopelman said in 2014. "It was a combination of moments: watching her with my nephew. Traveling with her. Going to museums with her. I knew, adding them up, this was it."
Parenting seemed to strengthen their bond. "Honestly, I don't know how it is for other couples but really I like watching him be a father," Barrymore told PEOPLE in 2015. "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."
Sources told PEOPLE that the couple butted heads on where to live, with Kopelman preferring to stay in N.Y.C. and Barrymore "being drawn to" L.A. "They've had marriage issues for a while," a source said.
The estranged pair told PEOPLE in a statement: "Sadly our family is separating legally, although we do not feel this takes away from us being a family. Divorce might make one feel like a failure, but eventually you start to find grace in the idea that life goes on. Our children are our universe, and we look forward to living the rest of our lives with them as the first priority."
Five years after Kopelman and Barrymore's divorce, he wed Alexandra Michler, Vogue's director of fashion development, with Frankie and Olive serving as flower girls. Barrymore said she "adores" Michler, and that they all co-parent their girls well together.
"I just feel like I won the lottery with her, like, I really did," Barrymore said of Michler. "I feel like I'm lucky that there's this new beautiful soul that came into our lives."
Barrymore added, "I don't try to be her best friend, she knows that I absolutely worship the ground she walks on, and I'm her biggest cheerleader."
Barrymore said she gives Michler and Kopelman space, but that they're all friends. "We hang out. We do dinners, all the kids' birthdays. We might take a trip together," she said. "We're finding our way in a beautiful, slow, respectful manner."
In December 2022, Barrymore opened up about her divorce to PEOPLE, calling it "the death of a dream."
She added: "There was no scandal. Nothing went wrong, which is cleaner, but makes it harder and more confusing because there isn't The Thing to point to. We tried so hard to make it work."