Brad Pitt and his girlfriend, Ines de Ramon, arrived at Athens airport in Greece on February 19 before heading to the island of Hydra, where Pitt is set to begin filming his new film, The Riders. This public display marked one of the few times the couple has been seen together since their relationship became known, drawing attention to what many are calling a genuine Brad Pitt Greece romance.
The couple’s arrival in Greece displayed a relaxed yet fashionable vibe. Pitt, 62, dressed for comfort with a cream bomber jacket layered over a knit sweater and T-shirt, accessorized with a baseball cap and sunglasses, paired with loose jeans. De Ramon, 33, wore beige pants and a long leather jacket, complementing her look with sunglasses and a black leather Gucci travel bag.
An Evolving Romance in the Public Eye
Pitt and Ines de Ramon have maintained a notably private relationship since they were first linked in November 2022. Their first public appearance together was in July 2024 at the F1 British Grand Prix, shortly after de Ramon’s divorce from Paul Wesley was finalized earlier that year. Despite speculation that their appearance was a calculated move to promote Pitt’s film F1, which is currently competing for Best Picture at the 2026 Oscars, Pitt denied any intentional publicity stunt.
No, dude, it’s not that calculated,
he said in a May GQ interview.
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 added,
My personal life is always in the news,
continuing,
It’s been in the news for 30 years, bro. Or some version of my personal life, let’s put it that way. It’s been an annoyance I’ve had to always deal with in different degrees, large and small, as I do the things I really want to do.
Since his 2016 separation from Angelina Jolie, with whom he shares six children—Maddox, 24, Pax, 22, Zahara, 21, Shiloh, 19, and twins Knox and Vivienne, 17—Pitt has appeared to adopt a more measured approach to managing his private life amid the spotlight.
Reflecting on his current personal life, Pitt said, My life is fairly contained, adding,
It feels pretty warm and secure with my friends, with my loves, with my fam, with my knowledge of who I am that it’s like this fly buzzing around a little bit.
Brad Pitt’s Early Relationships in the Spotlight
Before his current relationship with Ines de Ramon, Brad Pitt’s love life garnered attention through various significant partnerships and romances.
First Romances of the 1980s
In the 1980s, Pitt dated singer Sinitta on and off for several years. When asked in 2016 about a hypothetical nickname for their relationship, she cheekily suggested Braditta. Around the same period, Pitt was rumored to have dated actress Shalane McCall, who starred as his on-screen girlfriend in four episodes of Dallas between 1987 and 1988. However, McCall married Trent Valladares in 1989 and largely moved on from those rumors.
Engagement and Heartbreak with Jill Schoelen
Pitt’s first engagement was to actress Jill Schoelen, his co-star in Cutting Class. Their engagement lasted three months, during which Schoelen asked Pitt to visit her in Budapest while she was filming a movie. Pitt later shared with The Sun in 2011,
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,
describing his journey. He continued,
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.’
This experience underlined the unpredictable nature of early relationships for the actor.
Robin Givens and Mike Tyson’s Anecdotes
Pitt appeared on actress Robin Givens’ sitcom Head of the Class in early 1989. Givens had recently divorced boxing legend Mike Tyson. Tyson later recounted a humorous encounter at Givens’ home, saying,
She drives up with the handsome Brad Pitt,
as part of a story on NBC’s Conan in 2012. Tyson added,
I said, ‘aw man, I ain’t gonna get no p–sy, f–k.’
Comedian Andy Richter quipped,
Brad Pitt is the international symbol for that.
Tyson revisited the tale on The Real in 2016, concluding,
I didn’t really catch them in the act—maybe before the act…He’s a really nice guy.
Late 1980s to Early 1990s Relationships
Pitt’s romantic life during this period included dating Christina Applegate, whom he accompanied to the 1989 MTV Video Music Awards. Though Applegate has kept details private, musician Sebastian Bach claimed he interrupted Applegate’s date with Pitt that night.
Also during 1989, Pitt dated E.G. Daily, best known as Dottie from Pee-Wee’s Big Adventure. Daily later described him as laid back, very earthy, adding,
He’s the kind of guy that would pick up and leave and drive his car just to get out of the city,
in an interview with DailyMail.com in 2016.
Breakthrough Roles and Off-Screen Romance
Pitt’s breakout role in 1991’s Thelma & Louise saw him play a hustling hitchhiker opposite Geena Davis, with whom he developed a real-life relationship, according to Davis. She recalled an audition story to The Hollywood Reporter in 2014:
I actually read with him first—there were five candidates for the role,
and added,
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.’
Notable Relationships and Personal Reflections in the 1990s
Pitt had a meaningful relationship with Juliette Lewis during the early 1990s. They played turbulent couples in films like the 1990 TV movie Too Young to Die? and the 1993 thriller Kalifornia. In 1992, Pitt accompanied Lewis to the Oscars when she was nominated for Cape Fear. Reflecting on their time together in a 1995 Vanity Fair interview, Pitt said,
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?
Lewis later told Pop Tarts in 2010,
run into each other on and off and we say hello and that is really nice.
Brief Relationship with Thandiwe Newton During Filming
Pitt described his experience working on Interview With the Vampire as difficult but said it sparked his love for New Orleans. The shoot also launched a brief romance with Thandiwe Newton, who played Yvette, a servant in the film.
Rising Fame and Relationships in the Mid-1990s
In 1994, Pitt attended the Legends of the Fall premiere with Czech model Jitka Pohlodek, during a time he confided to Vanity Fair that he still loved Juliette Lewis.
His connection with Gwyneth Paltrow became one of Hollywood’s most iconic mid-1990s romances. They met on the set of 1995’s Se7en and frequently appeared in public together, known for their style and chemistry. After Pitt won the Best Supporting Actor Golden Globe for 12 Monkeys in 1996, he referred to Paltrow as his
angel, the love of my life,
and they became engaged that December. Paltrow told Entertainment Tonight about her serious commitment,
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,
but the pair ended their relationship in June 1997.
In 1998, Paltrow reflected on their breakup, saying,
When two people aren’t supposed to be together, they’re not supposed to be together,
and later admitted to Howard Stern in 2015,
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.
She also revealed the impact their split had on her family, noting,
My father loved him like a son.
Paltrow confessed,
I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!
Later 1990s and Early 2000s Romances
Following the end of her engagement with Pitt, Claire Forlani was briefly linked to him during their collaboration on Meet Joe Black. The two attended the 50th Annual Writers Guild Awards together, sparking romance rumors.
Jennifer Aniston met Pitt on a blind date arranged by their agents in 1998. At the time, the couple was simply known as Hollywood’s golden pair without any catchy portmanteau. They married in 2000, and Pitt made a guest appearance on Friends in 2001. On starting a family, Aniston stated in 2002,
Absolutely it will happen but probably not for a while.
However, their marriage ended, and they announced a formal separation on January 8, 2005, explaining,
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,
with their divorce finalizing in October of that year. Despite a very public breakup, the two have remained friends in recent years.
The High-Profile Relationship and Divorce with Angelina Jolie
Pitt later admitted that his and Angelina Jolie’s romance began during the 2004 filming of Mr. and Mrs. Smith while Pitt was still married. Their relationship matured over the next decade, and they eventually wed in 2014 at their French chateau after two years of engagement. Together, they raised six children—Maddox, Zahara, Shiloh, Pax, and twins Knox and Vivienne.
Jolie described their connection shortly before their wedding, saying,
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,
continuing,
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.
Despite their long history, Jolie filed for divorce in September 2016, citing irreconcilable differences. This filing sparked an FBI investigation into allegations about Pitt’s conduct on a flight, though he faced no charges. The couple’s relationship remained tumultuous over the ensuing years, eventually concluding with a divorce settlement in late 2024 after an eight-year legal dispute.
Present-Day Relationship with Ines de Ramon
Since Pitt’s breakup with Jolie, rumors circulated linking him with various women, including Alia Shawkat, jewelry designer Sat Hari Khalsa, and architecture professor Neri Oxman, but all were ultimately labeled as friendships. His current relationship with jewelry executive Ines de Ramon stands out as his most public and serious since.
Pitt was first spotted with de Ramon in November 2022, just two months after her separation from Paul Wesley became public. Wesley officially filed for divorce in February 2023. Since then, sightings of Pitt and de Ramon together, though not constant, have continued consistently, suggesting a stable and genuine partnership.
The Significance of Brad Pitt’s Greek Sojourn
Brad Pitt’s recent trip to Greece with Ines de Ramon signals an important chapter in his personal and professional life. As he embarks on filming The Riders on Hydra, the couple’s presence and their low-key display of affection highlight a transition to a more settled phase for the Hollywood star. Their Grecian outing not only fuels public interest in Pitt’s love life but also underscores his efforts to cultivate balance amid fame and ongoing creative pursuits.
This rare public glimpse into Brad Pitt Greece romance underscores a quieter, more grounded dynamic compared to the intensity and unpredictability that characterized much of his previous relationships. As he prepares for new roles and navigates private happiness, audiences and fans alike will continue to watch how this fresh romance shapes the actor’s future both on and off the screen.
