A walk through Brad Pitt’s star-studded dating history

UPDATED MAY 20, 2020 12:10 PM EDTMAY 20, 2020, 12:10 PM EDT

Former model and increasingly lauded actor Brad Pitt is famous not only for his myriad roles onscreen but for his high profile love life. From being spotted on the red carpet with Christina Applegate , through his ill-fated engagement with Gwyneth Paltrow and his two marriages with Jennifer Aniston and Angelina Jolie , here we take a look back at one of Hollywood’s hottest leading men’s interesting and varied love life, who has been linked with actresses, singers and voice-over artists.

The Once Upon a Time in Hollywood star even acknowledged the interest during the 2020 awards season. “I wanted to bring my mom, but I couldn’t because any woman I stand next to, they say I’m dating,” he joked during his Golden Globes acceptance speech. “It would just be awkward.”

Christina Applegate

The pair went on a date at the MTV Movie Awards in 1989, however, all did not go to plan as Christina ditched Brad during the evening and left with a mystery man! Poor Brad!

Sinitta

Who’d have thought that Simon Cowell and Brad Pitt would have dated the same lady? The pair attended the 1988 Smash Hits Poll Winners Party together but the romance was short-lived, with Sinitta resuming her on-off relationship with the X Factor judge.

Robin Givens

Brad, meanwhile, took solice in the arms of The Fresh Prince Of Bel-Air actress Robin Givens, going on a string of dates in 1989.

E.G. Daily

E.G. Daily, who voiced Tommy Pickles in Rugrats, also caught the Thelma & Louise star’s eye in 1989.

Juliette Lewis

After falling for each other while shooting Too Young To Die, the couple ended up dating between 1989 and 1993. Opening up about the relationship with Vanity Fair, Brad revealed: “I still love the woman. There’s some real genius there. I had a great time with her. It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”

Gwyneth Paltrow

They met on the set of horror classic Se7en in 1994 and soon became one of Hollywood’s hottest couples. By 1996 they were engaged, with Brad calling Gwyneth “the love of his life” at the Golden Globes. They never made it down the altar, however, with Gwyneth later claiming that Brad was “too good for her.”

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Jennifer Aniston

And then came Jen. They met on a blind date in 1998 after their agents set them up. “I will say this about Jen: She‘s fantastic, she’s complicated, she’s wise, she’s fair, she has great empathy for others... and she’s just so cool,” he told Rolling Stone. They got hitched in 2001 in Malibu with guests including Jennifer’s Friends’ co-star Courteney Cox and Salma Hayek . Their love story came to an end in 2004.

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Angelina Jolie

‘Brangelina’ as they were dubbed met on the set of Mr & Mrs Smith with Brad adopting her son Maddox and daughter Zahara in 2006, the year they had their first biological child, Shiloh , together. When accused of breaking up Brad and Jennifer, Angelina responded: “To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive. I could not look at myself in the morning if I did that. I wouldn‘t be attracted to a man who would cheat on his wife.”

The couple went on to adopt a third son, Pax in 2007 and have twins Knox and Vivienne in 2008. The pair married on August 23, 2014, in an intimate ceremony at their Château Miraval estate in Correns, France. They shocked the world by announcing their separation in September 2016.