15. Sinitta
Brad Pitt broke free from only dating the actress-type to take a British pop-singer for a spin in the 80s. The relationship was a relatively high-profile one. Sinitta was actually found by Simon Cowell (and also dated him). The relationship between Pitt and Sinitta may have lasted for as much as two years or so. She was much more famous than Pitt at the time, but her fame has appeared to wane quite a bit since then with her latest stint, lately being a mere mentor on The X Factor. Sinitta has recently talked about her relationship with the heartthrob, saying that, “He was beautiful with the most beautiful body” and that, “He was fun, he was young and very sweet.” We can’t say we disagree with that statement.
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