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A Lookback at Brad Pitt's Former Loves

By Carol Cassada

Hollywood leading man is back on the market. After his divorce from Angelina Jolie was finalized, the star seems ready to date again. He's rumored to be dating actress Alia Shawkat. The two have reportedly been spending a lot of time together.

While there's been no confirmation about their relationship, this has Pitt's personal life once again in the tabloids. Throughout the years, Pitt has had two high-profiled marriages, and dated a few other actresses.

So while everyone continues to speculate over Brad and Alia, let's take a lookback at some of his former loves.

Juliette Lewis


It's hard to believe, but at tone time Pitt dated actress/singer Juliette Lewis. The two met on the set of the movie Too Young To Die?

Juliette was seventeen when she started dating Pitt, who was ten years her senior. Despite the age difference, the couple was madly in love. Pitt even accompanied Lewis to the 1992 Oscars when she was nominated for a Best Supporting Actress award for her role in Cape Fear.

Pitt and Lewis went on to star in another movie together called Kalifornia, but they split following the film's 1993 release.

Gwyneth Paltrow


Pitt has a thing for falling in love with his co-stars, and on the set of the 1995 movie Seven he met Gwyneth Paltrow. Pitt and Paltrow became one of Hollywood's most sought after couples. A year after dating, the couple became engaged.

However, no wedding plans were ever made and the couple called it quits in 1997.

Years later, Paltrow would open up about her split with Pitt. She said that even though she loved Brad, she was still young at the time and felt she wasn't ready for marriage.

Jennifer Aniston

Getty Images

When Brad Pitt began dating Jennifer Aniston in 1998, they were the talk of Tinseltown. The Hollywood leading man and the actress of America's favorite sitcom made waves with their relationship. They married in a star-studded ceremony in July 2000, which featured her co-stars from Friends in attendance.

The couple seemed madly in love as they walked the red carpet and talked about each other in interviews. Brad even made a guest appearance on Friends.

However, in January 2005, the couple stunned the world when they announced their divorce.

Angelina Jolie

A few months after announcing his split from Jennifer Aniston, Brad was seen hanging out with his Mr. & Mrs. Smith co-star Angelina Jolie. This led to speculation that the two had an affair and it led to Pitt's divorce from Aniston.

Pitt quickly became a father figure to Angelina's adopted children Maddox and Zahara. A year after going public with their relationship, Angelina gave birth to the couple's daughter Shiloh in May 2006. A few months later, Angelina would adopt another boy named Pax. In July 2008, Angelina gave birth to twins Knox and Vivienne.

Brad and Angelina become Hollywood's newest It couple as everyone clamored for photos of the couple and their children.

In August 2014, the couple decided to make things official when they married. However, their union would be short-lived when Angelina filed for divorce in September 2016.

In April 2019, their divorce became finalized.

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