Sinitta and Brad Pitt: A complete timeline of their unlikely 1980s romance
8 April 2026, 15:09
From a chance introduction to a two-year romance, here’s how the pop star and future Hollywood icon met, dated and broke up before Brad Pitt became a superstar.
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Long before Brad Pitt became one of Hollywood’s most recognisable leading men, he was simply a young actor trying to find his big break.
And, for a two-year window in the late 1980s, he was romantically linked to British pop star Sinitta.
Decades later, their short-lived relationship continues to resurface, most recently during Sinitta’s appearance on I'm a Celebrity... South Africa.
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So how did it all begin, and why did it end? Here’s a clear timeline of their relationship.
1986: the introduction (and initial rejection)
In 1986, Sinitta – whose full name is Sinitta Renet Malone – was a major name in UK pop, known for hits like 'So Macho' and 'Toy Boy'. Brad Pitt, by contrast, was relatively unknown, with a small role on the US soap Dallas.
According to Sinitta, their introduction came via industry connections. Speaking to The Sun, she recalled initially turning down the idea of meeting him.
Sinitta explained that she was often contacted by agents representing well-known men to gauge her interest in dating them. However, when Brad Pitt was first suggested to her around 1986, she initially declined.
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"When I was asked about Brad, I was like, ‘No, I’m not interested. Why would I date anybody I’ve not met?’. I didn’t know who he was. He was in Dallas at the time and I was more of a Dynasty fan."
That quickly changed when she saw a photo of him: “Later that day, though, I saw pictures of this gorgeous boy on the desk. I picked them up, waved them about and whispered to her, ‘Who is he? He’s cute’, and she said, ‘That’s the guy who wants to meet you’. I was like, ‘OK, yes. Get him on the phone’."
1986–1988: dating and a shared connection
After being introduced properly, the pair began dating and, by Sinitta’s account, connected immediately.
"We met and just clicked," she recalled. "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."
Their relationship unfolded during a transitional moment: Sinitta was enjoying chart success, while Brad was still building his career.
In 1988, they made a public appearance together at the Smash Hits Poll Winners’ Party, one of the biggest pop culture events in the UK at the time.
1988: the breakup
The relationship reportedly ended in 1988, with distance cited as the key issue.
"It was a long-distance thing for too long," Sinitta explained. "He was based in LA and had to be there for auditions and filming, whereas I was always off on tour. And I need my men to be around and be with me."
Communication at the time made things even harder: "We didn’t have the internet or WhatsApp back in the late '80s, all we had in those days was a fax or a phone or an answer machine.
"There wasn’t a lot of contact if you were in different countries and I found that difficult."
She also hinted that their communication styles didn’t quite align: "I used to spend a fortune telephoning him from hotels and sending 40-page faxes in the middle of the night.
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"But boys aren’t that good at communicating back, so I’d send these 40 pages and he’d come back with maybe a one-word answer... It fizzled out soon after."
Reflections on the relationship
Sinitta has spoken about Brad Pitt on multiple occasions over the years.
During a previous appearance on I'm a Celebrity... Get Me Out of Here! in 2011, she described their time together.
"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."
She also reflected on his later rise to fame, particularly after Thelma & Louise: "It was before he made Thelma & Louise but even I saw that movie and thought 'Oh my God, what have I done?'"
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After the split
Following their breakup, Brad’s career accelerated rapidly, eventually leading to high-profile relationships with Jennifer Aniston and Angelina Jolie.
Sinitta, meanwhile, remained a familiar figure in British entertainment and maintained a long-standing personal connection with Simon Cowell.
When asked in 2011 to compare the two men, she responded playfully: "Who do you think?" She also added that Pitt was: "Beautiful with the most amazing body."
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2016: reunion rumours (sort of)
Years later, Pitt’s split from Angelina Jolie sparked light-hearted speculation about a reunion.
Appearing on Alan Carr's New Year Specstacular, Sinitta joked about the idea: “We did! We did. He has been calling and you know what I said? ‘Brad. Move on’.”
2026: the story resurfaces
The relationship has once again entered the spotlight thanks to Sinitta’s return to reality TV.
During a recent episode of I'm a Celebrity... South Africa, fellow contestant Scarlett Moffatt asked her about the romance.
Reflecting on it now, Sinitta said: "Even I do think, wow, it was nice while it lasted."
She added: "All I have to do is close my eyes and there he is," to which Scarlett joked: "I’d be napping all the time."
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