The Stunningly Awful Love Life Of Drew Barrymore

Drew Barrymore might be Hollywood royalty — with generations of Barrymore actors in her family including father, John Barrymore Jr., not to mention being the godchild of Steven Spielberg, who directed her in "E.T.," and Sophia Loren — but of course, especially these days, she's known for much more than her lineage. Many have dubbed her America's Sweetheart for her constant bright smile, positive attitude, and appearances as an endearing, hapless heroine in rom-coms like "Never Been Kissed," "50 First Dates," and "Music and Lyrics."

But as many of her biggest fans know, Barrymore basically grew up in front of the camera, first known for her roles in "E.T. the Extra-Terrestrial," "Firestarter," and "Irreconcilable Differences." In her teens and early 20s came movies like "Bad Girls" and "The Wedding Singer," her first of three film ventures with co-star Adam Sandler. Barrymore would continue to act through the 2000s, including starring in the box office hit film series, "Charlie's Angels," navigating fame and publicity through the multitude of men she's dated along the way, never quite finding the soulmate she likely was seeking.

Sometime around 2015, the actor claimed she was swearing off men for five-years — yet it would seem at least one man slipped through her defenses. Whether or not that palate cleanse worked in her favor, let's just take a stroll down Barrymore's memory lane of significant others who were in her life over the last thirty plus years.

Drew Barrymore and Corey Feldman both grew up in front of the camera as child stars, then became teen heartthrobs. But the similarities don't stop there. They were both emancipated from their parents as teens and each have been candid about growing up in an industry that's difficult to navigate even as an adult, let alone a child, being exposed to people and things they weren't equipped to handle. Ironically, they both appeared in a CBS Schoolbreak Special called, "15 and Getting Straight."

It makes sense the two would find comfort, a certain connection, with each other. After appearing in the CBS special, the two briefly dated, though Barrymore was only 14, while Feldman was 18. The two appeared publicly at several events including showing up at the Oscars together in 1989, Feldman already having appeared in a slew of big screen movies like "Gremlins," "The Goonies," and the Oscar nominated "Stand By Me." In fact, looking back on that time, Barrymore remembers Feldman as being a bigger star than herself. While interviewing Alfonso Ribeiro on her series, "The Drew Barrymore Show," she mused, "We were both, like, in the Corey Feldman circle." To which, Ribeiro responded, "Yes, we were part of the Corey Feldman circle of crazy."

According to TeddyFeed, Feldman reported in his memoir "Coreyography" that it was actually Barrymore's mother who first set them up. Feldman also admitted that at the time they were dating, he was a substance abuser, while Barrymore was working hard to remain sober.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

By 1991 it would seem that Drew Barrymore had already lived a lifetime of experiences at only 16 years old — a successful actress, a recovering addict, an emancipated adult, a published author with her memoir "Little Girl Lost" releasing that same year, and apparently, engaged to be married.

According to a 1991 People article, Barrymore was engaged to Leland Hayward, who at the time was 24 years old. Hayward also came from an influential and famous Hollywood family as his grandfather was agent and producer, Leland Hayward, his grandmother actor Margaret Sullavan, and his father, William L. Hayward, was a producer known for "Easy Rider" and who tragically died by suicide in 2008.

But a Hollywood dynasty pairing was not to be, and it wasn't long after that the actor was not only linked to actor/singer Jamie Walters but the two announced their engagement. In 1992, a carefree Barrymore appeared on the "Arsenio Hall Show" and talked about her photoshoot for Interview magazine in which she appeared nude, lying next to a shirtless Jamie Walters. There were also "pool party" type images of Barrymore with other female actors, prompting rumors she might be bisexual. Barrymore told Hall she was very comfortable in the shoot. "I'm not offended by the hype about it," she said, adding "I think that it's really beautiful." She also admitted fiancé Jamie was "very jealous." And though she told Dennis Miller, "He's just the sweetest, most wonderful man I ever met," the relationship wouldn't make it past 1993.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ by dialing 988 or by calling 1-800-273-TALK (8255)​.

In 1994, Drew Barrymore was still just 19 years old. She'd just appeared in "Bad Girls," a western in which she played a gun-wielding sex worker along with Madeline Stowe and Andie MacDowell. But above all, she was engaged for the third time — well, she might have skipped that part. Sometime in early 1994, Barrymore wed Jeremy Thomas, a 32-year-old bar owner.

Barrymore shared all the details of their whirlwind wedding while on "The Tonight Show with Jay Leno," telling him she'd been married for one month — after dating for one and a half months — and that Thomas had accompanied her to the premier of "Bad Girls." The two, according to Barrymore, got married at the bar, the same night Thomas asked her. How did they pull it off so quickly? "This woman came," she said, clarifying, "We found her in the Yellow Pages." The actor also revealed that the woman who married them was also a psychic and told her the couple had known each other in a past life. Barrymore continued she was skeptical but the woman insisted they were meant to be together. "It was fun and we could giggle, and we had all the people that we really love there and it was great," she said.

Unfortunately the union would barely last two months as the Tampa Bay Times would report the couple filed for divorce with LA Superior Court, citing irreconcilable differences, coincidentally the name of one of Barrymore's first movies.

With the book closed on her first (and very brief) marriage, Drew Barrymore was back on the market, but it wouldn't be long at all before she was in yet another committed relationship. This time with Hole guitarist, Eric Erlandson. In fact, according to a June 1995 article in Rolling Stone, the pair were dating most of the 11-months it took for her to get a divorce from Jeremy Thomas.

Barrymore told the magazine that she had three chance encounters with Thomas, one including him following her out of a bar when she was sick, making sure she was okay. After running into him two more times, he invited her back to his place to listen to music. And it wasn't long after that when the actor would move in with the musician. "I love him so much," Barrymore told the publication, "And I have a family now from Eric, too." Barrymore also told the Los Angeles Times, "I'd marry Eric in a heartbeat."

However, when asked if the couple would get married on "The Tom Snyder Show," she replied, "We're just happy being together." By April of 1996, Erlandson and Barrymore still appeared to be together as they showed up to the premiere of the Richard Gere film "Primal Fear." It must have been around this time the two called it quits — if you want to do the math. During a December 1996 appearance on "Bobbie Wygant," to promote her film "Scream," Barrymore mentioned she'd been seeing someone for seven months.

When Bobbie Wygant asked Drew Barrymore during a December 1996 interview who her boyfriend is, she wouldn't give the name. "You know it's funny because we've been going out for seven months and nobody knows we're together," she said, adding that she felt like it was the "best relationship in the whole world." When pressed by Wygant, she only shared that he was an actor and his hometown was Dallas — the same city one of her co-stars in the film "Best Men" calls home. That would be Luke Wilson.

Barrymore explained further that it wasn't tough to keep the relationship a secret because they didn't do "Hollywood" things and spent more quiet time together, walking, watching movies, or taking their dogs to the creek. Barrymore seemed to relay that this less visible type of relationship was a nice change.

Of course, they eventually went public and began being seen out together, as well as appeared in more movies together, including starring together in "Home Fries." The couple was still together in 1998 when "Hard Copy" did a feature on their relationship and credited Wilson for helping to transform Barrymore from "wild child" to a more mature woman. Unfortunately, a quiet breakup happened in 1999, but a 2022 segment on "The Drew Barrymore Show" would reveal more details about her relationship. While reminiscing with Kate Hudson about dating the Owen brothers, Drew revealed, "It was an open relationship. We were young."

In September of 2020, Drew Barrymore had comedian Tom Green on her talk show – not just her former "Charlie's Angels" co-star, but the man who was her second husband. According to what Green revealed on the show, the two hadn't spoken in 15 years. The mood between them was genuine and sweet—though if you look closely, there was significant "gazes locked" happening at times. Even though Green had his new puppy in his lap, aptly named Charlie.

After Green gushed over Barrymore, her show, and how great it was to see her, Barrymore shared their backstory for the viewers, saying that she had admired his work so much that she asked him to be a part of "Charlie's Angels." The two would come out as a couple before the movie released in October of 2000 and then marry in July of 2001. Sadly, they barely made it to the end of the year before Green filed for divorce, per People.

A tearful Barrymore also reminisced about meaningful times she spent with Green and his family, telling a story of staying at the parents' lake house. She said, "I was like, yeah, this is what, you know, safety and contentedness feels before you're going to sleep. And I will never forget that night. And I love your parents and I really love you and I celebrate you." Green appeared touched, saying, "I was so happy when you invited me on the show. It's been too long ... It's nice to reconnect."

Drew Barrymore met The Strokes drummer, Fabrizio Moretti, in April of 2002 at a concert in California, per Zimbio. After her divorce from Tom Green was finalized, Barrymore showed up in New York to visit Moretti, and the pair were spotted outside Barney's. During the time the two were romantically involved, Barrymore had a handful of movie releases including, "Charlie's Angels: Full Throttle," "50 First Dates," and "Fever Pitch." Which means, the couple was looking like they might make it for the long haul.

In January of 2007, Barrymore spoke openly to Harper's Bazaar about her longtime beau, saying, "You need to reinvent your relationship if you want to continue being together." She went on to share that this was the longest relationship she'd been in. Maybe she forgot to knock on wood — or maybe the magazine delayed publishing the article — because that same month it was reported that the actor dumped the drummer.

At least Barrymore has a lasting memory from the relationship. She told ET viewers in her "Dear Drew" segment in May of 2021 about the most romantic gesture a guy has done for her, going back to her time with Moretti. She was to appear in an "SNL" skit as a drummer for The White Stripes, and Moretti taught her to play the song, "Seven Nation Army." "That, I thought was really romantic. To get to learn a skill set that I didn't really have," she said.

Drew Barrymore and Justin Long may have first worked together on the set of "He's Just Not That Into You," but Long was definitely into the "Charlie's Angels" star. The two ended up dating for about nine months in 2007 to 2008 before they broke up. According to E! News, Long was shaken up and had to pull out of a movie project Barrymore was producing and starring in.

Meanwhile it appeared during their "we were on a break" time, Barrymore was seen out with actor Ed Westwick of "Gossip Girl" fame. HuffPost reported that Barrymore and Westwick were seen making out at a Kings of Leon concert. In the summer of '09 there were rumors they might be back together (after being spotted out together, PDAs and all), but those appearances could have been due to the forthcoming movie they were both starring in: "Going the Distance," which the relationship did not.

In September 2022, Barrymore interviewed yet another of her exes on her series, "The Drew Barrymore Show." After a long lingering hug, the former couple seemed relaxed and giddy to be reunited. Of their time together, Barrymore said, "We laughed so much. Like that was so much a part of our connection." But it wasn't all pleasant memories. When Barrymore burst into tears, Justin pulled her into a hug. "I feel like we've been through so much together, too," she said, describing the relationship as "hedonistic" and "chaos." Despite it all, Long said, "I cherish that time."

In 2011, reports of Drew Barrymore seeing a new man starting coming out. The actor this time found Will Kopelman, an art consultant and the son of former Chanel CEO Arie Kopelman; the pair dated for a little more than a year before getting married in June of 2012. Kopelman told Oprah in 2013 — as Barrymore held their new baby, Olive — that he and Barrymore were friends for about four years before they began dating. "I kinda knew when we were friends, like this is the sort of person I want to be with." Olive's sister, Frankie, followed in 2014, but sadly, the couple announced their separation in 2016.

In a "Sunday Sitdown" interview with Today in 2020, Barrymore shared that divorce hit her pretty hard, especially given the fact that her own parents divorced when she was young, and it was the last thing she wanted for her own daughters. But one of things that helped get her through the process and move forward was Kopelman's family and the fact that everyone was coming together for their girls. Still she says after five years, "I don't think I've recovered from that." And to that she adds, "I think I'm equally as scared to find love again as I would be as if it never happened."

By August of 2016, Drew Barrymore and Will Kopelman were officially divorced, and Barrymore was likely focusing on raising her daughters and filming her forthcoming Netflix series, "Santa Clarita Diet." And while she might not have been ready to find love again, a girl's gotta have some fun, right? In 2017, the actor was linked to businessman David Hutchinson, who is the senior vice president at Maesa, the company that makes and markets Barrymore's Flower Beauty products. The rumors were sparked by two random Instagram photos the actor posted in June of 2017 — photos Hutchinson was not in — where she tagged the businessman. Per an exclusive report to Us Weekly, they'd also been seen holding hands.

Then pics were snapped of the couple out in public, including one of Barrymore driving Hutchinson in her car after a lunch date, per US Weekly. A source told ET, "Drew and David are serious. They have a great time hanging out together and Drew is so happy! She loves how great he is with her daughters."

By 2019, whatever had been happening between Hutchinson and Barrymore was over. On Valentine's Day 2019, Barrymore posted an Instagram selfie in which there were positive affirmations stuck to the mirror she was looking into. After musing about all the love she had for her family and friends, she shared it had been almost four years since she "successfully" dated. "So I'm not sitting around bummed out. I feel stupid grateful. But I'm still a romantic at heart," she wrote.

Drew Barrymore has been interviewed multiple times by Howard Stern over the years, and more recently about her struggles with being single and the dating world. "This façade of a dating app is really hard to whittle through," she told Stern in 2021 on "The Howard Stern Show." Stern listened, and in October of 2022, the radio host took action, with the help of his wife, Beth. According to The Things, Howard and Beth felt they could help her by coming up with potential suitors — one of which, per the article, a man Beth dated — to participate in a "Dating Game" on Stern's radio show.

The four bachelors — Josh Radin, Clarke Thorell, Diego Lopez, and Jon Blitt — were posed interesting questions/scenarios including one from Jimmy Fallon, who asked each of them to come up with a song for Barrymore. While Barrymore didn't want to pick one of the bachelors, she knew Stern wouldn't let that fly and ultimately selected Bachelor #2, actor Clarke Thorell. The reason? Well, it was so Drew! During the game, Stern had asked what the guys would do if Chris Rock insulted Drew at an awards show. After the answers, Barrymore said, "It was Bachelor #2 when he said, 'I would take her hand,' I almost burst into tears ... Do you know how f*****g long it's been since someone has taken my hand and I felt safe with them?" Only time will tell if Stern helped her find a forever match.