Top Women Brad Pitt Has Dated

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As a long-time fan, I’ve always noticed how Brad Pitt’s relationships seemed to grow alongside his career. It’s fascinating to see how, from his early work on TV shows to the big movie projects and industry gatherings he’s been a part of, each phase of his life has had pretty clear dates and moments we all remember. It’s like you can trace his journey – both professionally and personally – through these well-documented milestones.

This list highlights relationships that have been well-documented, with specific information like the date they first met, the length of their relationship, times they were seen together in public, and official milestones like engagements or marriages. If a relationship began through a shared project, the name of that project is shown in single quotes to keep things clear and consistent.

Jennifer Aniston

Brad Pitt and Jennifer Aniston started dating in the late 1990s, after meeting through their agents. They got married in Malibu in July 2000. Throughout the early 2000s, they were frequently seen together at movie premieres and award ceremonies. During this time, he was working on films such as Fight Club and Ocean’s Eleven, while she was a star on the show Friends.

The couple announced they were separating in January 2005, and their divorce was completed later that same year. They described the breakup as friendly, and they continued to appear together publicly from time to time, most notably in 2020 when they participated in a table read of ‘Fast Times at Ridgemont High,’ which received a lot of media coverage.

Angelina Jolie

Brad Pitt and Angelina Jolie first met on the set of ‘Mr. & Mrs. Smith’ in 2005, and their romantic relationship became known to the public later that same year. Over the next ten years, they grew their family through both having children and adoption, all while frequently traveling the world and dedicating themselves to acting and charitable work.

The couple wed at Château Miraval in France in August 2014, including their children in the celebration. Then, in 2016, Jolie initiated divorce proceedings, which involved deciding on child custody and, later, disagreements about the future of their shared winery in France.

Gwyneth Paltrow

Brad Pitt and Gwyneth Paltrow first met on the set of ‘Se7en’, which came out in 1995, and quickly became a highly publicized couple during the mid-1990s. After dating for two years, they announced their engagement in 1996, with Paltrow frequently displaying her engagement ring at public appearances and in interviews that year.

In 1997, they called off their engagement and announced the breakup with statements that avoided any public disagreement. Even after the split, they both continued to support ‘Se7en’ through later releases and discussions, but kept a professional distance while still recognizing their past connection in interviews.

Juliette Lewis

Brad Pitt and Juliette Lewis first connected around the time of the 1990 film ‘Too Young to Die?’ and later collaborated on ‘Kalifornia’, which came out in 1993. They were a couple for several years in the early 1990s, and were seen together at premieres for those films and other Hollywood events. Their relationship lasted throughout the beginning of the decade.

As a movie buff, I always found it interesting to learn about Brad Pitt’s early relationships. From what I’ve gathered, he and his partner split up in the early nineties, *before* he really hit it big with films like ‘Interview with the Vampire’ and ‘Legends of the Fall’. Everything I’ve read from that time suggests their relationship was over *before* his career took off in the mid-nineties, which gives us a pretty solid timeframe for when they went their separate ways.

Christina Applegate

Brad Pitt and Christina Applegate had a short relationship in 1989, when both were starting out in their careers – Applegate was known for her role on ‘Married with Children’ at the time. They made a public appearance together at the MTV Video Music Awards that year, bringing their relationship into the spotlight.

Their short-lived collaboration concluded shortly after that public event, and both individuals pursued other endeavors. This partnership is still remembered as a clear example of Brad Pitt’s early career, and is often included in articles detailing his professional journey and looking back at his past work.

Jill Schoelen

Brad Pitt began dating actress Jill Schoelen after they met while working on the 1989 horror film ‘Cutting Class’. They even got engaged during this time, and the engagement was discussed in interviews and publicity related to the movie’s release. This was a significant relationship for both of them.

I remember when their engagement sadly ended in 1989, after what felt like a brief time together – they both went on to focus on their own careers in film. It’s actually a really clear-cut part of Brad Pitt’s early dating life, because we know exactly when it began and ended – it makes it one of the easiest periods to pinpoint. It’s fascinating to look back on!

Sinitta

In the late 1980s, Brad Pitt was dating British singer Sinitta. This was when he was starting his career in Hollywood and she was popular in the UK music scene. Their relationship involved frequent travel between the US and the UK, and they often talked about each other in television interviews and magazine articles from that period.

They ended their relationship before Brad Pitt became famous with his early nineties films. Both have consistently said the relationship happened before his rise to fame, and this matches up with when those films were released and his career progressed.

E. G. Daily

Brad Pitt and E.G. Daily began dating in the late 1980s. At the time, Pitt was appearing in guest roles on TV shows, while Daily was pursuing both acting and a music career. Their relationship is remembered in interviews discussing those early years, when they were both frequently at auditions and recording sessions.

Their relationship ended before Brad Pitt became well-known in the early nineties. Since both of them talked about this time in interviews later on, it’s easy to connect it to his work on shows like ’21 Jump Street’ and her voice work on ‘Rugrats’.

Let us know in the comments which part of Brad Pitt’s dating history you found most surprising. Share your thoughts and tell us what stood out to you!

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2025-10-04 15:17