Relive Brad Pitt's Star-Studded Dating History: From Gwyneth Paltrow to Angelina Jolie

Take a trip down romance lane with the Ad Astra actor

By Jess Cohen Sep 13, 2019 4:41 PMTags
Gwyneth Paltrow, Brad PittBarry King/WireImage.com

Brad Pitt's love life is making headlines once again.

The Ad Astra actor, who has had relationships with a number of A-list stars over the years, just took a trip down romance lane while on The Ellen DeGeneres Show. During Friday's episode of the talk show, Pitt and host Ellen DeGeneres reflected on their friendship, remembering where they first met.

"I remember, Melissa Etheridge's pool party," Pitt said of their first meeting, which took place in the late '80s or early '90s. "Where I think you were hitting on my girlfriend. I think so, I was flattered!"

"I actually, since then, have dated another one of your girlfriends," DeGeneres laughed as she told Pitt. "We'll talk about that later."

From 2000 to 2005, Pitt was married to Jennifer Aniston. Following their split, Pitt began a relationship with Mr. & Mrs. Smith co-star Angelina Jolie, who he later tied the knot with in 2014. The couple went on to call it quits in 2016, with Jolie filing for divorce citing irreconcilable differences.

photos
Brad Pitt's Dating History

Prior to his relationships with Aniston and Jolie, Pitt was spotted spending time with a number of famous faces, including Gwyneth Paltrow, who he was once engaged to.

Let's take a look back at Pitt's star-studded dating history!

Sinitta

The "Toy Boy" singer dated Pitt off and on for several years in the '80s, long before every couple had a clever one-word nickname—so when the pop star was asked in 2016 what their cutesy name could've been, she suggested "Braditta."

Shalane McCall

Brad played the actress' boyfriend Randy on four episodes of Dallas between 1987 and 1988 and was rumored to have romanced her off-camera as well. But in 1989, when she was 17, McCall married current hubby Trent Valladares and never looked back.

Jill Schoelen

Pitt's first fiancée! The Cutting Class co-stars had been engaged for three months when, claiming loneliness, Schoelen pleaded with Pitt to visit her in Budapest, where she was shooting a movie. "At this point I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her," Pitt reportedly told The Sun in 2011. "I got there, went straight to the set where she was filming and that night we went out to dinner. She told me that she had fallen in love with the director of the film. I was so shocked I said, 'I'm outta here.'" Love works in mysterious ways.

Robin Givens

Pitt scored an appearance on the Riverdale actress' sitcom Head of the Class in January 1989. The ink on Givens' divorce from Mike Tyson wouldn't be dry until that February, however, and the boxing champ later recalled seeing Pitt toking away when he came across him at his estranged wife's house one morning—where Tyson says his intent was to have a quickie while on his way to see his divorce lawyer.

"She drives up with the handsome Brad Pitt," he said while telling the story, then a sample anecdote from his one-man show, on Conan in 2012. "I said, 'aw man, I ain't gonna get no p--sy, f--k.'" Andy Richter chimed in, "Brad Pitt is the international symbol for that."

The tale continued to be a favorite for interviewers over the years, with Tyson concluding on The Real in 2016, "I didn't really catch them in the act—maybe before the act...He's a really nice guy."

Christina Applegate

Pitt was the Married...With Children star's date to the 1989 MTV Video Music Awards—and though she has remained mum on the subject, Skid Row rocker Sebastian Bach insists that he was the guy Applegate infamously ditched her up-and-coming-actor date for that night.

E.G. Daily

Pitt also dated Dottie from Pee-Wee's Big Adventure in 1989. He may have had that rebel look, but Daily would later describe him as a "laid back, very earthy" guy, and not "super Hollywood." "He's the kind of guy that would pick up and leave and drive his car just to get out of the city," she told DailyMail.com in 2016.

Geena Davis

Pitt rocked Davis' world onscreen as a hustling hitchhiker in 1991's Thelma & Louise, which proved to be the actor's (and his abs') true breakout role—and Pitt's onetime roommate Jason Priestley claimed in his 2014 memoir that they were an off-screen item as well. 

"I actually read with him first—there were five candidates for the role," Davis recalled Pitt's audition to The Hollywood Reporter in 2014. "And then he came in—this is so embarrassing—but I got a little distracted during the scene, you know? I was forgetting my lines. I was like, 'I'm totally screwing up this kid's audition.'"

Juliette Lewis

These two played murderously dysfunctional couples twice, in the 1990 TV movie Too Young to Die? and the gritty 1993 thriller Kalifornia, but real life seems to have been sweeter during the several years—he was her Oscars date in 1992 when she was nominated for Cape Fear—they were together.

"I still love the woman," Pitt told Vanity Fair in February 1995. "There's some real genius there. I had a great time with her...It was one of the greatest relationships I've ever been in. The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?" In 2010 Lewis told Pop Tarts that she and Pitt "run into each other on and off and we say hello and that is really nice."

Thandie Newton

Brad has described his experience making Interview With the Vampire as "miserable." He told Entertainment Weekly in 2011 that "the great thing that came out of that movie is that it birthed my love affair with New Orleans." 

But the shoot also birthed a brief relationship with Newton, who had a small role as Yvette, a servant on Pitt's character Louis' plantation.

Jitka Pohlodek

The Czech model was Brad's date to the 1994 premiere of Legends of the Fall, which sent the actor's heartthrob status skyrocketing—and they were dating when Pitt told Vanity Fair he still loved Juliette Lewis.

Gwyneth Paltrow

Pitt's the one who lost his head for Paltrow on the set of 1995's Se7en. They were the mid-90s couple, from the top of her slip dress to the ends of his frosted tips. Accepting the Best Supporting Actor Golden Globe for 12 Monkeys in 1996, Brad thanked Gwyneth, his "angel, the love of my life," and he proposed that December. They even had matching haircuts at one point.

"I take the institution extremely seriously. There are no divorces in my family either—and in his either, so this is not something—we've been together for quite some time, so this is not a rash decision," Gwyneth convincingly told Entertainment Tonight about their engagement. But in June 1997, they broke up.

"When two people aren't supposed to be together, they're not supposed to be together," a defiant Paltrow said in 1998. Fast-forward to 2015, when she told Howard Stern, "I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me."

Moreover, her dad, Bruce Paltrow, was "devastated" when they broke up. "My father loved him like a son." Ultimately, Paltrow said, "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!"

Claire Forlani

After his breakup with Gwyneth, Brad's said to have briefly dated his Meet Joe Black co-star. They attended the 50th Annual WGA Awards together.

Jennifer Aniston

The story goes that Jen met Brad in 1998 on a blind date set up by their agents. The world still not one for smushed-together names yet, they were simply "Hollywood's golden couple." They married in 2000, Pitt guest-starred on Friends in 2001 and in 2002 Aniston said of starting a family, "Absolutely it will happen but probably not for a while."

Alas, on Jan. 8, 2005, the actors announced they had "formally" separated. "For those who follow these sorts of things, we would like to explain that our separation is not the result of any speculation reported by the tabloid media," they said in a statement. The divorce was finalized that October amid all sorts of reports perpetuated by the people who do follow these sorts of things.

Meanwhile, Aniston's September 2005 Vanity Fair interview will go down in history as one of the rawest, most poignant breakup postmortems in celebrity history.

Angelina Jolie

It took a few years, but the Oscar winner would ultimately indicate that she and Pitt had indeed fallen in love during the making of Mr. and Mrs. Smith...in 2004.

Pitt went to Ethiopia with her when she adopted her second child, Zahara, in 2005—and he formally adopted Zahara and Maddox in 2006. Daughter Shiloh was born in May 2006, Jolie adopted Pax in 2007 (Pitt followed suit in 2008), and twins Knox and Vivienne were born in 2008. Spurred on by their kids, Brangelina (nicknames being very much in vogue by the time they got together) finally married at their chateau in France in 2014 after being engaged for two years.

"You get together and you're two individuals and you feel inspired by each other, you challenge each other, you complement each other, drive each other beautifully crazy," Jolie told Elle in 2014, before the surprise nuptials. "After all these years, we have history—and when you have history with somebody, you're friends in such a very real, deep way that there's such a comfort, and an ease, and a deep love that comes from having been through quite a lot together."

The following year, Pitt told British GQ (not talking about marriage, per se, but still), "I've always believed happiness is overrated, you know? It's those difficult times that inform the next wonderful time, and it's a series of trade-offs, of events, of wins and losses."

Jolie filed for divorce on Sept. 19, 2016, citing irreconcilable differences and requesting primary custody of the kids. It took about five months to be on speaking terms again, but the dust settled and up rose a tentative co-parenting arrangement and a lot of soul-searching.

"Well, there's a lot to tell [the kids] because there's understanding the future, there's understanding the immediate moment and why we're at this point, and then it brings up a lot of issues from the past that we haven't talked about," Pitt said in GQ Style's Summer 2017 issue. "So our focus is that everyone comes out stronger and better people—there is no other outcome."

Latest News