Gwyneth Paltrow, Brad Pitt

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Brad Pitt's love life is making headlines once again.

The Ad Astra actor, who has had relationships with a number of A-list stars over the years, just took a trip down romance lane while on The Ellen DeGeneres Show. During Friday's episode of the talk show, Pitt and host Ellen DeGeneres reflected on their friendship, remembering where they first met.

"I remember, Melissa Etheridge's pool party," Pitt said of their first meeting, which took place in the late '80s or early '90s. "Where I think you were hitting on my girlfriend. I think so, I was flattered!"

"I actually, since then, have dated another one of your girlfriends," DeGeneres laughed as she told Pitt. "We'll talk about that later."

From 2000 to 2005, Pitt was married to Jennifer Aniston. Following their split, Pitt began a relationship with Mr. & Mrs. Smith co-star Angelina Jolie, who he later tied the knot with in 2014. The couple went on to call it quits in 2016, with Jolie filing for divorce citing irreconcilable differences.

Prior to his relationships with Aniston and Jolie, Pitt was spotted spending time with a number of famous faces, including Gwyneth Paltrow, who he was once engaged to.

Let's take a look back at Pitt's star-studded dating history!

Sinitta, Brad Pitt


Brad Pitt, Shalane McCall

Jim Smeal/WireImage

Brad Pitt, Jill Schoelen

Ron Galella/WireImage

Robin Givens, Brad Pitt

Vinnie Zuffante/Archive Photos/Getty Images

Christina Applegate, Brad Pitt

Barry King/Getty Images

E.G. Daily, Brad Pitt

Barry King/WireImage

Geena Davis, Brad Pitt

Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images

Juliette Lewis, Brad Pitt

Ron Galella/WireImage

Thandie Newton, Brad Pitt

Getty Images

Jitka Pohlodek, Brad Pitt

Jim Smeal/WireImage

Gwyneth Paltrow, Brad Pitt

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Claire Forlani, Brad Pitt


Brad Pitt, Jennifer Aniston

Gregg DeGuire/Getty Images

Angelina Jolie, Brad Pitt, Cannes

Pascal Le Segretain/Getty Images

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