Gwyneth Paltrow's Dating History, Including Brad Pitt, Ben Affleck and More

Gwyneth Paltrow's dating history is A-list.

The Academy Award-winning actress has dated some of Hollywood's most eligible bachelors, starting with her first public romance with actor Donovan Leitch Jr. in 1993, and she's shared glimpses into those relationships with fans over the years.

In December 2022, Paltrow — who has dated Ben Affleck, been engaged to Brad Pitt and married Coldplay's Chris Martin — spoke about her relationship with her exes during an Instagram Story Q&A session, revealing that she's on good terms with former partners.

"Pretty much. I really believe in conscious uncoupling," the GOOP mogul wrote. "When you spend meaningful time with someone, it's nice to have it morph into friendship. I don't want to have bad blood with anyone, ever (if I can help it)."

Her most notable "conscious uncoupling" is with ex-husband Martin, with whom she amicably co-parents her daughter, Apple, and son, Moses, and about whom she often speaks about their continued good friendship.

"I think Chris and I were meant to be together and have our kids," Paltrow said in 2019. "But our relationship is much better like this: friends and co-parents and family."

Pitt and Paltrow also recently revisited their friendship in 2022; Pitt said "it's lovely" to have Paltrow "as a friend now," to which Paltrow replied, "It is."

These days, Paltrow raves about her love with husband Brad Falchuk. In 2021, Paltrow called the Glee creator "such a special, amazing man."

Here's a look back at Paltrow's past romances through the years.

Donovan Leitch Jr.

Paltrow was linked to actor Donovan Leitch Jr. — son of "Mellow Yellow" singer Donovan Leitch — from 1993 to 1995. The two had a head-turning reunion in Sept. 2013 when they shared a friendly kiss on the lips at a Los Angeles Dodgers baseball game.

At the time, Paltrow was still married to ex-husband Chris Martin when the friendly exchange happened and Leitch Jr. told the Daily Mail in March 2014 that the kiss was "purely" platonic.

"I was just saying goodbye to her. It was purely innocent," the actor explained to the outlet. "We were sitting in the owner's box in front of 30,000 people with her two children right next to us. That isn't exactly the setting for a secret liaison."

Robert Sean Leonard

Paltrow was rumored to have dated actor Robert Sean Leonard, who portrayed Neil Perry in the 1989 film Dead Poets Society, for a year in the early '90s. According to E! News, the former couple kept their relationship very private.

The outlet reports Leonard spoke briefly about his time with Paltrow in 1998, telling the New York Post their split was "the funniest breakup I've ever had."

"We were in her apartment, figured we shouldn't see each other anymore, and within five minutes she was saying, 'You know who you'd like? I have this friend'... Gwyneth's a bit of a yenta, but she's a great, great friend," he reportedly said.

In June 2022, Paltrow left cheeky comment on co-star Ethan Hawke's Instagram of throwback Dead Poets Society photos, saying she "wished" she "would've made out with more" of the movie's stars. (The cast also included Robin Williams, Josh Charles, Leonard and more.)

Brad Pitt

Paltrow and Brad Pitt dated from 1994 to 1997, but called it quits just a few months after getting engaged. They were, as Paltrow told Vogue, "a very '90s couple."

The actors met while filming the movie Seven in 1994 and started dating shortly afterward. "I knew immediately," Pitt later told Rolling Stone of falling for Paltrow on set. "I got within 10 feet of her, and I got goofy. I couldn't talk," he said.

Meanwhile, Paltrow said she was "oblivious" to Pitt's feelings. "I had no idea. I thought he was just really friendly," the actress told the Los Angeles Times of her former co-star in August 1996. "And then I started getting a crush on him."

They dated for two years (complete with matching haircuts) before Pitt proposed to her while filming Seven Years in Tibet in Argentina in December 1996. Six months after announcing their engagement, Hollywood's golden couple shocked fans with their split.

"I think I was a kid and I wasn't ready. He was too good for me," the Country Strong star said during a 2015 appearance on The Howard Stern Show. "I honestly do think I was too young and didn't know what I was doing."

Paltrow noted in 2020 that she and Pitt "don't have any really bad blood." In June 2022, the friendly exes reunited for an interview on Goop's website, when Pitt said that "it's lovely" to have Paltrow "as a friend now," to which Paltrow replied, "It is."

Ben Affleck

Paltrow and Ben Affleck relationship began after meeting at a party hosted by now-disgraced studio mogul Harvey Weinstein in the late '90s. The former couple previously dated on-and-off from 1997 to 2000, during which they starred together in 1998's Shakespeare in Love and 2000's Bounce.

The couple shared quick wit and a wicked sense of humor — but their relationship also had its share of ups and downs. In 2015 interview with Howard Stern, Paltrow said that dating Affleck was fun, but her parents did not approve.

"He's super intelligent and really, really talented and he's funny," she said at the time. "But he wasn't in a good place in his life to have a girlfriend." Still, they clearly enjoyed one another's company.

The pair broke up in 1999, but briefly reunited before finally ending things in 2000. The GOOP mogul and Affleck remain pals, however. "I like him," she told Stern. "I'm still friends with him."

In May 2022, Paltrow reflected on her past relationships with both Pitt and Affleck during her appearance on the Call Her Daddy podcast. Host Alex Cooper asked her a series of straight-forward questions, including which of the two were better in bed.

"Brad was like the sort of major chemistry, love of your life, kind of, at the time and then Ben was, like, technically excellent," Paltrow laughed before adding, "I can't believe my daughter is listening to this!"

Luke Wilson

Paltrow co-starred alongside actor Luke Wilson in 2001's The Royal Tenenbaums. The two reportedly dated for one year after meeting on set of the film. While few details are known about their relationship, Paltrow described her ideal man to Harper's Bazaar at the time she was rumored to be dating Wilson.

"He's tall and thin, but muscular, to start with the superficial. A gentleman," she said in the 2001 interview with the outlet. "Someone who's well educated, funny, witty, artistic, and has a lot of integrity. He doesn't have to grab all the attention in the room. A good kisser."

Chris Martin

Gwyneth Paltrow and Chris Martin were married for more than 10 years before they famously announced they were "consciously uncoupling" in 2014. The pair first met in 2002 while hanging backstage at one of Martin's Coldplay concerts.

They began dating and wed one year later in December 2003. Over the course of their decade-long marriage, Paltrow and Martin welcomed two children, daughter Apple in May 2004 and son Moses in April 2006.

In March 2014, Paltrow and Martin shocked fans when they announced they were splitting up in a post on the Goop website titled "Conscious Uncoupling." In April 2015, the separated pair finalized their divorce.

Despite their split, Paltrow and Martin continue to co-parent Apple and Moses. Plus, Goop founder and Coldplay frontman have remained close friends.

"I think Chris and I were meant to be together and have our kids," Paltrow said in 2019. "But our relationship is much better like this: friends and co-parents and family."

Brad Falchuk

Paltrow and her husband Brad Falchuk first met in 2010 during the actress' guest appearance as substitute teacher Holly Holliday on the hit musical comedy series Glee. At the time, Paltrow was married to Martin, and the Glee co-creator was married to producer Suzanne Bukinik.

After splitting from their respective spouses, the couple quietly began dating in August 2014. Around one year later, Paltrow and Falchuk made their relationship public at the actress' friend and costar Robert Downey Jr.'s 50th birthday party in April 2015.

The pair then secretly got engaged in 2017 before marrying in 2018, with Paltrow telling PEOPLE she considered their nuptials her first wedding. After tying the knot, the newlyweds flew to the Maldives to enjoy a honeymoon and ring in 2019.

"I adore my husband. He's brilliant and deeply kind. I feel like he's a real equal too," Paltrow said of Falchuk during a September 2019 interview with InStyle. "And he pushes me in the best ways. I really like being married. It's fun."

In 2021, Paltrow called Falchuk "such a special, amazing man." She's continued to pen sweet tributes to her husband (who's not active on Instagram) since.