In the history of Hollywood, few names evoke as much intrigue, glamour, and tabloid frenzy as Brad Pitt. Today, the F1 star celebrates his 62nd birthday, looking as timeless as ever while continuing to dominate the global box office. But beyond the blockbuster hits and the “Sexiest Man Alive” titles lies a dating history that reads like a chronicle of pop culture itself.
Brad Pitt, star of the upcoming Formula One based movie, F1, walks in the Paddock prior to practice ahead of the F1 Grand Prix of Hungary at Hungaroring on July 19, 2024 in Budapest, Hungary. (Photo by Mark Thompson/Getty Images)
From era-defining marriages to quiet romances, Pitt’s journey in love has been just as transformative as his legendary roles. As he enters a new year, we’re revisiting the relationships that shaped the life of the industry’s most famous face.
A Timeline of Hollywood’s Most Famous Romance History
The Early Days: Juliette Lewis and Gwyneth Paltrow
In the early ’90s, a young Pitt was often seen with his co-stars. He dated Juliette Lewis (his Kalifornia co-star) for several years when they were both rising stars. However, his first “mega-couple” moment came with Gwyneth Paltrow. After meeting on the set of Se7en, the pair became the blonde, leather-jacket-wearing obsession of the mid-90s, even getting engaged before calling it quits in 1997.
The Golden Couple: Jennifer Aniston
Actor Brad Pitt and wife actress Jennifer Aniston attend the World Premiere of the epic movie “Troy” at Le Palais de Festival on May 13, 2004 in Cannes, France. Aniston wears a dress by Versace. (Photo by Evan Agostini/Getty Images)
In 1998, a setup by their agents led to the birth of “Brad and Jen.” Their 2000 wedding in Malibu was the pinnacle of Hollywood royalty. For five years, Jennifer Aniston and Brad Pitt were the industry’s most beloved pair, making their 2005 split a “where were you when it happened” moment for fans worldwide.
While their joint statement insisted the split was mutual, the world was rocked by rumors of an on-set affair between Pitt and his Mr. & Mrs. Smith co-star, Angelina Jolie. The scandal reached a fever pitch just weeks after the separation when photos emerged of Pitt and Jolie vacationing in Kenya.
Time has healed old wounds; as of today, Jennifer and Brad are friendly, often seen supporting each other at industry events and maintaining a respectful bond.
The Brangelina Era: Angelina Jolie
Actor Brad Pitt (L) and actress Angelina Jolie arrive at the 84th Annual Academy Awards held at the Hollywood & Highland Center on February 26, 2012 in Hollywood, California. (Photo by Jason Merritt/Getty Images)
Perhaps the most scrutinized relationship in history began on the set of Mr. & Mrs. Smith. Brad Pitt and Angelina Jolie—dubbed “Brangelina”—spent 12 years together, raising six children and advocating for global humanitarian causes. They officially wed in 2014, but the relationship ended in a 2016 filing that led to a complex, multi-year legal battle that has only recently begun to settle.
The Current Chapter: Ines de Ramon
Brad Pitt and Ines de Ramon attend the Apple Original Films & Warner Bros. Pictures “F1” World Premiere in Times Square on June 16, 2025 in New York City. (Photo by Dimitrios Kambouris/Getty Images)
After a few years of flying solo and sparking various dating rumors, Pitt found a new rhythm with jewelry executive Ines de Ramon. The pair was first linked in late 2022 and has since become a steady fixture at high-profile events, including this year’s British Grand Prix and the Venice Film Festival. Sources close to the actor suggest he is “happier than ever” as they recently moved in together in California.
