All the Famous Women Brad Pitt Has Romanced Michael, May 23, 2026May 23, 2026 Few Hollywood stars have had their love lives followed as closely as Brad Pitt. Across decades of fame, the Oscar-winning actor has been linked to actresses, models, and public figures whose own careers often made the relationships even bigger tabloid stories. Some romances became serious long-term partnerships, while others lasted only briefly or were heavily rumored at the time. Claire Forlani Source : Shutterstock Brad Pitt was briefly linked to actress Claire Forlani in the late 1990s. Reports about the romance emerged after the pair appeared together publicly several times, though neither openly discussed the relationship in great detail. Compared to Pitt’s more high-profile romances, this one remained relatively private and short-lived. Sinitta Source : Shutterstock Before Brad Pitt became one of Hollywood’s biggest stars, he reportedly dated singer and television personality Sinitta in the late 1980s. Sinitta later spoke publicly about their short relationship in interviews, describing Pitt as attractive, fun, and still relatively unknown at the time. Their romance did not last long, but it has become one of those surprising early-Hollywood connections fans still revisit today. Robin Givens Source : Shutterstock Brad Pitt was briefly linked to actress Robin Givens in the late 1980s. The relationship became widely discussed because Givens had recently separated from boxer Mike Tyson. Tyson later publicly claimed he once unexpectedly saw Pitt at Givens’ home during that period, turning the short-lived romance into part of celebrity pop-culture history. Jennifer Aniston Source : Shutterstock Brad Pitt and Jennifer Aniston became one of the most famous celebrity couples of the early 2000s. After being introduced by their agents, the pair quickly became media favorites. Their relationship combined two enormous television and movie stars at the height of their fame. They married in 2000 in a lavish Malibu ceremony that drew massive media attention. For years, they were viewed as one of Hollywood’s most stable and admired couples. The marriage ended in 2005, shortly after Pitt worked with Angelina Jolie on Mr. & Mrs. Smith. The separation became one of the most heavily covered celebrity stories of the decade. Juliette Lewis Source : Shutterstock Brad Pitt and Juliette Lewis became one of the young “it” couples of the early 1990s. The actors met while filming the television movie Too Young to Die? and later appeared together in projects including Kalifornia. Their relationship lasted for several years during the period when both actors were rapidly gaining attention in Hollywood. Lewis has spoken warmly about Pitt in later interviews, describing their relationship as meaningful during an important stage of both of their careers. Geena Davis Source : Shutterstock Brad Pitt was linked to Geena Davis after they worked together on Thelma & Louise in 1991. Their chemistry on screen immediately caught attention, especially after Pitt’s breakout role in the film helped launch him into mainstream fame. Reports about a real-life romance followed soon afterward. Angelina Jolie Source : Shutterstock Brad Pitt’s relationship with Angelina Jolie became one of the biggest celebrity stories of the 2000s. The actors met while filming Mr. & Mrs. Smith in 2004, and rumors about their chemistry dominated entertainment headlines for months. Pitt and Jolie later became publicly known as “Brangelina,” one of the most recognizable celebrity nicknames ever created by the media. Over the years, they built a large family together and became known not only for films and red carpets, but also for humanitarian work and international travel. Thandiwe Newton Source : Shutterstock Brad Pitt and Thandiwe Newton were reportedly linked in the mid-1990s after working together on Interview with the Vampire. The relationship was never heavily publicized compared to some of Pitt’s other romances, but entertainment reporting at the time connected the two actors socially and romantically for a period. Gwyneth Paltrow Source : Shutterstock Brad Pitt and Gwyneth Paltrow became one of Hollywood’s most glamorous couples during the 1990s. They met while filming Se7en and quickly turned into a major celebrity pairing. Their matching blonde hairstyles and frequent red-carpet appearances became iconic celebrity-magazine material of the decade. The couple became engaged in 1996, but they eventually separated before marrying. Paltrow later described herself as emotionally immature at the time, while still speaking respectfully about Pitt in later interviews. Kate Hudson Source : Instagram/katehudson Brad Pitt and Kate Hudson were the subject of heavy dating rumors in 2016 and 2017. The speculation became widespread online and in entertainment media, though multiple reports later suggested the rumors had been exaggerated. Hudson herself joked publicly about the attention. Ella Purnell Source : Instagram/ella_purnell Brad Pitt was briefly linked by tabloids to actress Ella Purnell after she became connected to one of his production projects. The rumors gained attention partly because some commentators noted that Purnell resembled Angelina Jolie. However, reports about an actual romance were never strongly confirmed. Charlize Theron Source : Instagram/charlizeafrica Brad Pitt and Charlize Theron sparked dating rumors in 2019. Entertainment outlets reported that the two stars had spent time together through professional connections, but later reports suggested the romance had likely been overstated or short-lived. Ines de Ramon Source : Shutterstock Brad Pitt has been linked to Ines de Ramon since 2022. Unlike many of Pitt’s earlier celebrity relationships, de Ramon comes primarily from the business and fashion world rather than acting. The pair have been photographed together at multiple public events, including film-related appearances and private gatherings with friends. Featured Image Source : Shutterstock Entertainment & Media