The Truth About Brad Pitt's Relationship With Gwyneth Paltrow

Long before she helmed her a multi-million-dollar Goop empire, putting a price tag on the wellness movement, Gwyneth Paltrow was an up-and-coming actor romantically entwined with silver-screen favorite Brad Pitt. The Oscar-winning star is no stranger to dating famous men, having had entanglements with some of Hollywood's most sought-after talent.

While many know about her 13-year marriage to Coldplay frontman Chris Martin, ending in their ever-so-mocked "conscious uncoupling," and her current highly publicized marriage to "Glee" co-creator Brad Falchuk, few remember her on-again-off-again thing with Ben Affleck, and fewer still her passionate relationship with Brad Pitt.

Long before Brangelina was a household name, and well before the internet freak-out about Paltrow's teenage daughter Apple looking exactly like her, Paltrow and Pitt were drawing all eyes to their red carpet appearances. From the truth behind their identical haircuts to the reason they ended so suddenly, here's everything you need to know about the former It couple.

Directed by thriller auteur David Fincher, "Se7en" stars Brad Pitt as a detective hunting down a serial killer. The incredibly dark drama just so happened to provide the right, if not unlikely, backdrop for romance, as Brad Pitt and co-star Gwyneth Paltrow met for the first time on set in 1994, playing husband and wife in the film (via Us Weekly).

Paltrow was in her early 20s when the pair first worked together, and it was a huge opportunity for the actor who had few credits to her name at the time. Pitt, on the other hand, had already made a name for himself, having emerged with his scene-stealing performance as a young sweet-talking scam artist in "Thelma & Louise" several years prior.

Soon after wrapping the film, Pitt and Paltrow went public with their relationship. Seen together in public constantly during their courtship, Paltrow even followed Pitt to Argentina to be with him during the filming of "Seven Years in Tibet."

Subverting the trope of the dad who hates his daughter's boyfriend, Bruce Paltrow, Gwyneth Paltrow's dad and prolific filmmaker in his own right, became absolutely enamored with Brad Pitt. In an interview on Gwyneth's Goop site in June of 2022, the starlet sat down with Pitt as he promoted his new clothing line in advance of Father's Day, recounting his intimate relationship with her own late father.

Gwyneth recalled a tender moment of her father talking about Pitt: "I'll never forget when we were engaged and he came to me one day, his eyes full of tears, and he said, 'You know, I never really realized what they mean when they say you're gaining a son. Like, I'm gaining a son.'"

When Gwyneth Paltrow asked Pitt if he felt a "paternal energy" from her own father, he replied "One hundred percent. I felt that same kind of guidance that you would get from a coach or a mentor." To this day, Pitt cites the late elder Paltrow as a role model.

A photo of Gwyneth Paltrow and Brad Pitt looking like twins makes the rounds on the internet every few years. You probably know the one –- the couple sports identical yellow-blond bobs on the red carpet for the 1997 premiere of "The Devil's Own," a film in which Pitt plays an IRA member who comes to stay with a friend stateside in order to pilfer firearms back to his native country.

Alongside the iconic picture is speculation that the couple must have gone to the same hairstylist to achieve the eerily similar looks. Finally putting the rumors to rest, Paltrow spoke on their twinning moment decades later. The star took to Instagram in a chat with her assistant, admitting that the blond pixie cuts were the product of hairstylist-to-the-stars Chris McMillan.

The matching 'dos weren't actually done on purpose on the part of either the hairdresser or the pair, but once the couple noticed what had happened, they decided to lean into it, wowing the tabloids not only with their stunning appearances but also their sense of humor (via Vanity Fair).

By now, the name Harvey Weinstein is synonymous with the systemic sexual abuse that has long plagued Hollywood. Back in the 1990s, however, it was more of an open secret, with many choosing to look the other way. As if we needed another reason to love Brad Pitt, he was one of the few celebrity men to not only believe women's stories, but also to stand up to Weinstein himself.

When Gwyneth Paltrow confided in then-boyfriend Brad Pitt that Weinstein had made a pass at her in a hotel room, Pitt publicly confronted Weinstein about it. On the "Howard Stern Show," Paltrow recalled what went down, saying that at the premiere of a play featuring one of her then-future "Shakespeare in Love" co-stars, Pitt went right up and chewed Weinstein out. "It was like the equivalent of throwing him against the wall, energetically," she told Stern. "It was so fantastic because what he did was he leveraged his fame and power to protect me at a time when I didn't have fame or power yet." 

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

While it might feel impossible to imagine a world where Gwyneth Paltrow isn't a fixture on the A-list, during her relationship with Brad Pitt, she was often accused of hitching her star to his to get better movie roles.

Paltrow already struggled to make a name for herself in the industry, as many assumed she was piggybacking on the success of her actor mother Blythe Danner and director/producer father Bruce Paltrow, even as she began proving her talent in meatier roles (via the Chicago Tribune). She told the paper, "I think it's taken me a lot longer than it would have taken anybody else to achieve respect, because first there was my mother, and people thought I was getting roles because of my parents. Then they said, 'Oh, she gets parts because of her boyfriend.'"

She proved all her haters wrong by going on to win Academy recognition for her leading part as Viola in "Shakespeare in Love." The unconventional period romantic comedy paved the way for her to break from her reputation as being linked to others' fame, becoming a respected artist on her own merit.

At the 53rd annual Golden Globe Awards in 1996, Brad Pitt won Best Supporting Actor for his role in "12 Monkeys," a science fiction thriller about a virus that poses a catastrophic risk to humanity. Laurence Fishburne and Alicia Silverstone announced the result, as Pitt was up against Ed Harris, John Leguizamo, Tim Roth, and Kevin Spacey (via Awards Show Network).

After thanking the "makers of Kaopectate," presumably because of his nerves, he went on to thank the Hollywood Foreign Press Association, the film's director, producer, production company, and a whole host of other cast-members, crew-members, agents, and the like, punctuating his speech with earnest moments of surprise.

Ever the charmer, he then made a sweet shoutout to his girlfriend. After thanking his family back home, he said a thank you to, "especially the love o' my life, my angel, Gwyneth Paltrow." The camera cut to Paltrow as she smiled with pride for her beau, with a hand placed delicately over her heart.

Early on in their relationship, Brad Pitt and Gwyneth Paltrow went on a trip to St. Barthelemy in the French West Indies. On this vacation, the couple evidently paid a visit to a nude beach, but it seemed to be Pitt who paid the biggest price, as two years later nude photos of him surfaced in an issue of Playgirl. In 1997, Pitt sued the publication for emotional distress and invasion of privacy. Ultimately he was able to get the judge to halt distribution of the issue, but unfortunately, copies that were already sent out were not to be recalled, and have since become something of a collector's item (per The Washington Post).

The picture leak happened well before celebrity nudes became almost commonplace, and even inspired Shania Twain, who name-checked Pitt in her hit song "That Don't Impress Me Much." She sang, "Okay, so you're Brad Pitt/That don't impress me much" (via Genius). She contests that it was never a dig at his appearance but rather a damnation of the hysteria surrounding celebrity nude leaks. "We see people naked every day. That's really what I thought. I wasn't picking on Brad Pitt," the singer-songwriter said in an interview with Billboard.

With so many public displays of affection (see Brad Pitt calling her the love of his life at the Golden Globes), and even the enthusiastic approval of her father, it came as no surprise that Brad Pitt proposed to Gwyneth Paltrow after two years of dating. 

Pitt spoke effusively about his love for her, but ultimately it wasn't enough. Paltrow decided that she was simply too young to settle down, and therefore had to call off the engagement, ending their relationship. At the time, she was just 25 years old to his 34, and the nine-year age gap proved to be too much, as they wanted different things.

She told Howard Stern in 2015, "I think I was a kid and I wasn't ready. He was too good for me ... I mean I was 22 when we met and it's taken me until 40 to get my head out of my ***. You can't make a decision when you're 22 years old." However much growing up she had to do, we can't help but admire how she was able to make the right decision for herself at the time, no matter how painful it was to split with Pitt.

Gwyneth Paltrow and Brad Pitt split in 1997, after she broke off their engagement. While Paltrow was working on her next project and would eventually meet Ben Affleck — beginning a hot-and-cold relationship that would last for years — Pitt's agent set him up on a blind date.

Proving that being a good-looking A-list celebrity has its perks, that blind date happened to be none other than "Friends" star Jennifer Aniston. The pair hit it off right away, and soon became the next Hollywood It couple, known simply as "Brad and Jen" (via Us Weekly).

After two years of dating, in 2000 they got married in a lavish Malibu ceremony that cost the couple a whopping $1 million dollars (via Brides). Unfortunately, it wasn't happily ever after for the couple, as they divorced in 2005, five years after the star-studded wedding. Only a few months after their marriage ended, Pitt began dating Angelina Jolie.

Decades after they ended things, when asked about her relationship to Brad Pitt, Gwyneth Paltrow has nothing but good things to say about her former paramour. While she admits they aren't friends per se, she still has so much love and admiration for him, and after their latest interview for her website, it's apparent that the feeling is mutual.

After discussing his latest business venture, a cashmere shirt brand, the conversation turned sentimental. "And it's lovely to have you as a friend now," Pitt said. "And I do love you," to which Paltrow responded, "I love you so much" (via Goop).

Paltrow happens to be on good terms with all of her exes, continuing to co-parent her children with Chris Martin following their split back in 2014. Now, she's happily married to "Glee" co-creator Brad Falchuk, which she referenced in her and Pitt's interview, saying, "I finally found the Brad I was supposed to marry. It just took me 20 years."