Sinitta's 'gorgeous' 2-year relationship with Brad Pitt before he found fame


The pop icon dated Brad Pitt between 1986 and 1988, before his breakout role as J.D. in the 1991 film Thelma & Louise shot him to international stardom


Sinitta and Brad Pitt dated from 1986 to 1988© Getty
Abby Allen
Abby AllenTV writer
April 7, 2026
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Pop icon and I'm a Celebrity... South Africa star Sinitta has a few famous exes, including Simon Cowell and David Essex, but there's one Hollywood heartthrob that viewers may not know she dated.

The 'So Macho' and 'Toy Boy' singer, 62, dated Brad Pitt, also 62, for around two years between 1986 and 1988. Sinitta has spoken about the relationship fondly in the past, including during her first appearance on I'm a Celebrity in 2011.

Sinitta on I'm a Celebrity… South Africa© ITV
Sinitta on I'm a Celebrity… South Africa

Speaking to model Emily Scott and McFly band member Dougie Poynter in the jungle, Sinitta reflected on what Brad was like: "Hot. He was beautiful, with the most amazing body. I saw him for two years.

"He was fun, he was young and very sweet. Some ardent fan gave me a slap when I came out of a supermarket over that relationship!"

WATCH: Sinitta at the HELLO! 2015 photoshoot

Sinitta dated Brad before his breakout role in Thelma & Louise, in which he starred opposite Geena Davis and Susan Sarandon. He then went on to star in Hollywood blockbusters like Fight Club, Troy and Mr. & Mrs. Smith, where he met his ex-wife, Angelina Jolie.

Speaking about the early point in his career when she knew him, Sinitta said: "It was before he made Thelma And Louise, but even I saw that movie and thought 'Oh, my God, what have I done?'" 

The role of J.D. was also famously turned down by George Clooney© Getty Images
The role of J.D. was also famously turned down by George Clooney

Inside Sinitta's relationship with Brad Pitt

In an interview with The Sun, Sinitta explained that Brad wasn't hugely known in the industry when she met him.

"He was in Dallas at the time and I was more of a Dynasty fan," she said, before deciding to meet up after seeing a "gorgeous" picture of him.

Sinitta on I'm a Celebrity… South Africa© ITV
Sinitta dated Brad before his breakout role

"We met and just clicked," she said. "We were both quiet people, Christian, normal and healthy people underneath our crazy, public lifestyles and, at that point, he wasn't really, really famous. He was just the hottest boy – drop-dead gorgeous.

"Everywhere we went, all the gay guys were after him, all the girls were after him. Everybody just loved him because he was stunning."

Why did they split up?

The couple were spotted together at the 1988 Smash Hits Poll Winners' Party, but reportedly parted ways due to distance and after Brad met British actress Emily Lloyd, daughter of Only Fools and Horses actor Roger Lloyd Pack.

Angelina Jolie in a pale pink dress with Brad Pitt at the Cannes Film Festival in 2009.© Anadolu via Getty Images
Brad went on to marry Angelina in 2014

Speaking to The Sun, Sinitta said: "People ask me, 'Why didn't we stay together?'. I don't know what really happened, but it was something to do with Emily. After that, we kind of just lost touch."

Brad was married to Jennifer Aniston from 2000 to 2005, before tying the knot with Angelina Jolie in 2014, although the couple split in 2016. Meanwhile, Sinitta dated The X Factor's Simon Cowell before marrying businessman Andy Willner in 2002. The pair later separated in 2010.

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