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Sinitta

In the late 80s, Pitt had a four year on-and-off relationship with “Toy Boy” singer, Sinitta. The pair called it quits and while the actor went on to make a name of his own in Hollywood, Sinitta went on to star in the U.K. version of “X-Factor” alongside ex-boyfriend, Simon Cowell.
(Image via Twitter)

A not-so-brief look at Brad Pitt's dating history

For nearly 30 years, Brad Pitt has cemented himself as one of the most powerful names in Hollywood both onscreen and off.

Although known as a leading man, the 55-year-old has quickly become one of the industry’s most powerful producers, lending his name to such critically acclaimed films as “The Departed,” “12 Years a Slave” and most recently, “Vice.”

ALSO SEE: Brad Pitt ‘in a good place’ with rumoured new girlfriend Charlize Theron

However when waxing poetic about William Bradley Pitt, his professional accolades are only part of the conversation. Pitt’s high profile relationships and public breakups have spawned perhaps more headlines than any other celebrity.

Now, two years after his split from ex-wife Angelina Jolie, the actor is back in the news for his rumoured new relationship with Oscar-winning actress, Charlize Theron.

Whether love is in the cards for Pitt and Theron, we thought we’d take a trip down memory lane and revisit the A-lister’s dating history.

Check out the gallery for a full Brad Pitt relationship timeline.

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