Top Women Brad Pitt Has Dated

Brad Pitt’s relationships have often intersected with the projects and places that defined different stages of his career. From early days on television sets to partnerships formed around major film productions and industry events, each chapter followed clear timelines and well documented milestones.

This list focuses on relationships that are widely reported with concrete details like when they met, how long they dated, public appearances, and confirmed transitions such as engagements or marriages. Where a connection involved a project, the relevant titles are placed in single quotes for clarity and consistency.

Jennifer Aniston

Brad Pitt and Jennifer Aniston began dating in the late nineties after being introduced by their representatives and they married in Malibu in July 2000. They appeared together at multiple premieres and award shows through the early 2000s while he worked on films like ‘Fight Club’ and ‘Ocean’s Eleven’ and she was starring on ‘Friends’.

They announced their separation in January 2005 and finalized their divorce later that year. Both called the split amicable at the time and they continued to have occasional public interactions in later years such as a 2020 table read of ‘Fast Times at Ridgemont High’ that drew widespread attention.

Angelina Jolie

Brad Pitt and Angelina Jolie met while filming ‘Mr. & Mrs. Smith’ which was released in 2005 and their relationship became public later that year. They built a family through birth and adoption during the following decade while traveling widely and working across acting and humanitarian commitments.

They married at Château Miraval in France in August 2014 with their children involved in the ceremony. In 2016 Jolie filed for divorce and the legal process included custody arrangements and later disputes related to their former winery business in France.

Gwyneth Paltrow

Pitt and Gwyneth Paltrow met while filming ‘Se7en’ which was released in 1995 and they became one of the most covered couples of the mid nineties. They got engaged in 1996 after two years of dating with Paltrow showing the ring at events and interviews that year.

In 1997 they ended the engagement and issued statements confirming the split without public conflict. Both continued to promote ‘Se7en’ during reissues and retrospectives in later years while maintaining professional distance and acknowledging their shared history in interviews.

Juliette Lewis

Brad Pitt and Juliette Lewis met around the 1990 film ‘Too Young to Die?’ and later worked together on ‘Kalifornia’ which was released in 1993. Their relationship lasted several years at the start of the decade and they made red carpet appearances tied to those projects and other industry events.

They separated in the early nineties before Pitt’s breakthrough in ‘Interview with the Vampire’ and ‘Legends of the Fall’. Interviews from the period consistently place their timeline ahead of his mid decade rise which provides a clear marker for when the relationship ended.

Christina Applegate

Pitt and Christina Applegate dated briefly in 1989 when both were early in their careers with Applegate starring on ‘Married with Children’. They attended the MTV Video Music Awards together that year which placed their connection in a specific public setting.

The brief relationship ended soon after that appearance and both moved on to other projects. The pairing remains a well documented snapshot of Pitt’s pre breakthrough years that is frequently referenced in career timelines and retrospective pieces.

Jill Schoelen

Brad Pitt dated actress Jill Schoelen after meeting on the 1989 horror film ‘Cutting Class’. They became engaged during that period and their engagement was acknowledged in interviews and promotional coverage around the movie’s release.

The engagement ended in 1989 after a short duration and both pursued separate paths in film. The clear start and end dates tied to the production make this one of the most straightforward early chapters in Pitt’s dating history.

Sinitta

Pitt dated British pop singer Sinitta in the late eighties when he was working to establish himself in Hollywood and she was active on the UK charts. The relationship included transatlantic visits and public references during television appearances and magazine features from that time.

They split before Pitt’s breakout film roles in the early nineties. Accounts from both have consistently placed the relationship in that pre fame window which aligns with known release dates and career timelines for each.

E. G. Daily

Pitt and E. G. Daily dated in the late eighties when he was taking guest roles on television and she was balancing acting and music work. Their connection is noted in interviews that recount those early years when both were moving between auditions and recording sessions.

The relationship concluded before Pitt’s higher profile roles arrived in the early nineties. Because both discussed that period in later interviews, the chronology is easy to place alongside his appearances on shows like ’21 Jump Street’ and her voice acting credits on ‘Rugrats’.

Share your thoughts on which chapter of Brad Pitt’s dating history surprised you most in the comments.