The Brad Pitt relationship timeline and recent double date have captured public attention, as the actor and his girlfriend Ines de Ramon stepped out with Gigi Hadid and Bradley Cooper for a notable evening in New York on June 13. This public outing marks another chapter in Pitt’s complex romantic journey, highlighting his past high-profile relationships and demonstrating his ongoing presence in both social circles and the headlines.
A Star-Studded Double Date in New York
Brad Pitt and Ines de Ramon, who have been seeing each other since 2022 after Pitt’s split from Angelina Jolie six years prior, recently enjoyed a double date with Gigi Hadid and Bradley Cooper at Cote Korean Steakhouse. The gathering underscored the growing openness of Pitt and de Ramon’s relationship in the public eye.
For the evening, Pitt chose a light blue silky shirt, wide-leg black velvet jeans, and dress shoes, leading the way with de Ramon at his side. She complemented him in a cream off-the-shoulder dress and nude heels, crafted for an elegant appearance. Cooper maintained a relaxed style in a black t-shirt and dark jeans, while Hadid favored a white tee, silver pants, and a denim jacket. Their double date not only turned heads but also highlighted the enduring appeal of high-profile Hollywood couples.
Hadid and Cooper, who are both parents from previous relationships, have been dating for over a year. They only recently went public with their romance via social media, following a celebration of Gigi’s 30th birthday this April.
“I feel so lucky to be 30!”
—Gigi Hadid, Model
Sharing moments from her birthday, including a celebratory kiss with Cooper, Hadid expressed gratitude for her life experiences and loved ones.
“I feel so lucky for every high and low—for all the lessons and gifts both have brought me. To get to feel it all! I’m so lucky to be a mom, friend, partner, sister, daughter, colleague to some of the most unbelievable humans!!”
—Gigi Hadid, Model
Brad Pitt and Ines de Ramon’s Discreet Connection
Pitt, at 61, and de Ramon, 32, have chosen to mostly avoid the glare of the spotlight. The couple was first seen together at a Bono concert in Los Angeles in 2022. They later appeared publicly at the British Grand Prix in July 2023. Pitt, whose divorce was finalized in December, responded to speculation that their presence at the Grand Prix was a calculated move to boost publicity for his upcoming movie about Formula 1 racing.
“No, dude, it’s not that calculated,”
—Brad Pitt, Actor
“If you’re living, oh my God, how exhausting would that be? If you’re living with making those kinds of calculations? No, life just evolves. Relationships evolve.”
—Brad Pitt, Actor
The actor’s remarks underscore his more organic approach to relationships following a history of public scrutiny.
The Early Years: Brief Romances and Rising Fame
Before Pitt’s relationships became headline news, his love life unfolded largely outside the spotlight. In the 1980s, he dated pop singer Sinitta on and off, with their playful dynamic earning retrospective nicknames. In the late ’80s, Pitt was involved with Shalane McCall, his co-star from “Dallas,” though she married soon after their rumored romance.
His first engagement was to actress Jill Schoelen. Their relationship ended unexpectedly after Pitt traveled to Hungary to visit her during a film shoot, only for Schoelen to reveal her feelings for another.
“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,”
—Brad Pitt, reportedly to The Sun
“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.’”
—Brad Pitt, reportedly to The Sun
This early breakup became a story Pitt would later recount with a hint of disbelief at love‘s unpredictability.
Unexpected Encounters and Wild Stories
During his ascent, Pitt encountered actress Robin Givens on her show “Head of the Class” in January 1989. At the time, Givens was in the process of divorcing boxer Mike Tyson, who recalled discovering Pitt in an awkward situation at Givens’ house. Tyson describing the moment, said:
“She drives up with the handsome Brad Pitt,”
—Mike Tyson, Boxer
“I said, ‘aw man, I ain’t gonna get no p–sy, f–k.’”
—Mike Tyson, Boxer
Andy Richter, present during Tyson’s retelling of the story on Conan, quipped:
“Brad Pitt is the international symbol for that.”
—Andy Richter, Actor/Comedian
Tyson later clarified the encounter years later, concluding:
“I didn’t really catch them in the act—maybe before the act…He’s a really nice guy.”
—Mike Tyson, Boxer
Fleeting Love and Industry Dates
In the same period, Pitt was linked with Christina Applegate, who took him to the 1989 MTV Video Music Awards before reportedly ditching him for rocker Sebastian Bach. That year he also dated E.G. Daily, known for her role as Dottie in “Pee-Wee’s Big Adventure.” Daily later described Pitt as an authentic, grounded individual.
“He’s the kind of guy that would pick up and leave and drive his car just to get out of the city,”
—E.G. Daily, Actress/Singer
Pitt became involved with Geena Davis during and after their collaboration on “Thelma & Louise,” as well as with Juliette Lewis, his co-star in two projects. Their relationship lasted several years, and Pitt continued to speak highly of Lewis after they parted ways.
“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?”
—Brad Pitt, Vanity Fair Interview
Juliette Lewis remembered their post-breakup interactions as friendly:
“run into each other on and off and we say hello and that is really nice.”
—Juliette Lewis, Actress (2010)
The 1990s: New Loves and Hollywood Partners
On the set of “Interview With the Vampire,” while Pitt later called the shoot “miserable,” he noted a key positive outcome:
“the great thing that came out of that movie is that it birthed my love affair with New Orleans.”
—Brad Pitt, Entertainment Weekly Interview
This period also saw a brief relationship with Thandiwe Newton, who played Yvette in the film. Pitt then dated Czech model Jitka Pohlodek, bringing her to the 1994 premiere of “Legends of the Fall.”
Brad Pitt’s romance with Gwyneth Paltrow blossomed during filming for “Se7en” in the mid-90s. Their highly publicized engagement capped two years of being Hollywood’s golden couple, culminating in heartfelt award speeches. Accepting a Golden Globe, Pitt thanked Paltrow as his
“angel, the love of my life.”
The relationship ultimately ended in 1997. Paltrow later spoke openly about their breakup, maturity, and her affection for Pitt.
“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 Paltrow, Actress
“When two people aren’t supposed to be together, they’re not supposed to be together,”
—Gwyneth Paltrow, Actress
“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.”
—Gwyneth Paltrow, Actress
Gwyneth also shared how strongly her father, Bruce Paltrow, felt about Pitt:
“My father loved him like a son.”
In reflecting on the relationship, she closed with,
“I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!”
—Gwyneth Paltrow, Actress
After his breakup with Paltrow, Pitt briefly dated “Meet Joe Black” co-star Claire Forlani, attending industry events together.
Hollywood Marriage and Separation: Jennifer Aniston
Pitt met Jennifer Aniston in 1998, and the couple quickly became a fixture in popular culture, marrying in 2000. Their partnership was marked by mutual support, with Pitt guest-starring on “Friends.” In 2002, Aniston said confidently about plans for children together:
“Absolutely it will happen but probably not for a while.”
—Jennifer Aniston, Actress
By January 2005, the couple announced their separation with a unified public message:
“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,”
—Brad Pitt and Jennifer Aniston, Joint Statement
The divorce was finalized in October 2005, but despite the very public split, the two eventually became friendly again.
The Jolie Era: Intense Love, Family, and Public Challenges
The timeline of Brad Pitt’s romantic journey shifted dramatically when he met Angelina Jolie filming “Mr. and Mrs. Smith” in 2004. Their connection, initially private, grew under media attention, with Jolie later admitting that their romance began while Pitt was still married.
Bonded by their growing family—Maddox, Zahara, Shiloh, Pax, Vivienne, and Knox—the couple eventually married at their estate in France in 2014. Jolie described the depth of their relationship after years together:
“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,”
—Angelina Jolie, Actress
“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.”
—Angelina Jolie, Actress
Despite their strong bond, Jolie filed for divorce in September 2016, and the separation prompted legal investigations and extensive media speculation. The highly publicized legal wrangling continued for eight years, concluding with a divorce settlement in late 2024.
Rumored Partners and Close Relationships
In the years following his split from Jolie, Brad Pitt was linked to a series of women, including Alia Shawkat, jewelry designer Sat Hari Khalsa, and architecture professor Neri Oxman. Although these relationships made headlines, none developed into official romances, and most were understood to be platonic friendships.
A New Chapter: Ines de Ramon
Pitt’s current relationship with Ines de Ramon, a jewelry company executive, seems to mark a shift toward stability. The couple was first publicly spotted together in November 2022, shortly after de Ramon and The Vampire Diaries actor Paul Wesley announced their own separation earlier that year. Reports of Pitt and de Ramon together have increased in frequency, even as they opt for a lower-key presence compared to his prior relationships.
The Broader Context and Cultural Impact
Brad Pitt’s romantic life has long fascinated both fans and media, from fleeting affairs to deep partnerships with figures like Jennifer Aniston and Angelina Jolie. His relationships frequently paralleled professional milestones, set in cities from Los Angeles and New York to France and Hungary. Along the way, other celebrities—such as Gigi Hadid, Bradley Cooper, and Claire Forlani—entered his personal narrative, weaving new connections across Hollywood generations.
What continues to distinguish the Brad Pitt relationship timeline and recent double date is the persistent public fascination with his evolving personal life. Each relationship, whether brief or significant, helped shape the actor’s story, reflecting broader trends in celebrity culture and the ever-changing dynamics of fame and privacy.
As Pitt and de Ramon embrace their relationship more openly, their story may be entering a more stable phase, while reminders of Pitt’s earlier romances—whether dramatic or joyful—remain part of his lasting legacy in Hollywood’s social fabric.
