Sinitta’s dating history: A look back at star’s list of famous exes from Brad Pitt to Simon Cowell

Sinitta, known for being a pop star legend and Simon Cowell’s BFF, has quite the impressive CV and candidly opened up to newmagazine in a new interview about her life now, including testing positive for coronavirus, and romance.

Describing herself as “chronically single,” the stunning 56 year old star added: “The past couple of years I’ve not been in a position to find love – I was just trying to stay alive and get healthy.”

She adds that she hasn’t been going on dating apps as a result of not feeling “confident.”

“I’d probably attract weirdos, people playing tricks on me when they realise I’m the Sinitta. I just need to be introduced to someone the old-fashioned way,” she added.

The star, whose recent health scare left her “borderline suicidal,” has some very famous exes to her name, including Brad Pitt himself, and she says she’s “had men say they’re intimated by [her] exes.”

So, here’s a look back at who Sinitta has dated over the years…

Simon Cowell

Sinitta, 56, who has adopted children Magdalena and Zac with ex-husband Andy Willner, opened up to new on her relationship with music mogul Simon Cowell and their 20-year, on-off relationship.

Speaking about Simon’s “harem of exes”, Sinitta said: "I’m a very possessive, jealous woman who has never shared a man in her life and never would. I have to be number one. There cannot be seven others! And that was the problem with Simon and I. Most guys would sleep with me, so the idea that I have to be a part of a harem is a real insult.”


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Sinitta feels that her close friendship with Simon, 60, isn’t unconventional by any means. She added: “It might be more conventional than you think. If you have good relationships with your exes, you can still be friends.”

Sinitta began dating Simon when she was just 14 years old and the pair were together on-and-off for 20 years.

Simon has been in a long-term relationship with Lauren Silverman since 2009 and the pair have a son named Eric together.

Brad Pitt

Sinitta and Brad Pitt were an item, on-and-off, for two years between 1986 and 1988.

Sinitta spoke about their time together while in the Australian jungle for I’m A Celebrity, saying: “[He was] hot. He was beautiful with the most amazing body. I saw him for two years.

"He was fun, he was young and very sweet. It was before he made Thelma & Louise, but even I saw that movie and thought, ‘Oh my God, what have I done?’"

Lifting the lid on their relationship to new, Sinitta added: “To be honest he was just a jobbing actor. He was in Dallas for a bit, but I never watched that, so I didn’t know or care if he was a good actor or not, he was just a really cute, fun guy who I fancied.”



Their relationship came to end as a result of long distance. Sinitta said: “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.”

She continued: “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. I used to spend a fortune telephoning him from hotels and sending 40-page faxes in the middle of the night.”

David Essex

Sinitta dated British pop star David Essex when she was young and admitted to having had a “crush on him all [her] life.”

Speaking to the Daily Mail, she said: “We had a love scene in the show, and when I first kissed him, I wanted to run round in circles screaming. I was mesmerised, completely captivated.

"He said I was “a keeper”, and gave me a Russian wedding ring from Cartier for my birthday.”

At the time, the pair were starring in the West End musical Mutiny! when their romance began.

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She continued: “People said: “What about the fact he’s so much older?” But I don’t think I saw anything except those twinkling eyes.”

At the time, Sinitta was dating Simon Cowell when she embarked on the 18-month romance with David Essex, who was 37.

She continued to tell the Daily Mail: “I didn’t fall out of love with Simon, but I’d just met my idol. If Simon had let me have a cheat card in those days, I’d have played it for David Essex.

"To be fair, Simon was quite a naughty boyfriend. There was another girl. She was a glamorous, sexy model. So I let her have Simon and let David have me.”

Andy Willner

Sinitta split from her husband Andy Willner in 2009 after seven years of marriage. Their divorce was finalised the following year.

She told Daily Mail at the time: “The truth is even now I don't know why he divorced me. Perhaps you had better ask him.

"He has never really explained to me why he went back to Hong Kong [from London] and the truth is that it still hurts.

"There was a lot of bitterness at first, as there is after divorce. We didn't talk for a year, but we were friends before we married and we are once again friends."

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It was with Andy that Sinitta adopted her children Zac and Magdalena in 2008.

Sinitta confided in Simon Cowell following her split with Andy and told new: “He’s the person I always went back to when I was single. He always said he’d never get married or have children, so that was a problem, because I wanted both.

“So I had to go off and marry someone else, adopt children, but when that relationship broke up, Simon and I still came back together.”

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