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#3 Sinitta

Believe it or not, Brad Pitt did not only date actresses. Sometime in the 80s the heartthrob dated British pop star Sinitta. Most of you probably recognize her as being Simon Cowell‘s ex-girlfriend, but she is, in fact, a pretty talented singer. Her biggest hits include “So Macho,” “Toy Boy” and “Match My Broken Heart.”

The British superstar was discovered by Cowell, so you can imagine she has had quite the interesting career. The beautiful Sinitta and Brad Pitt had a pretty high profile relationship and dated for more or less two years. The pair had a real relationship, it just came before Brad Pitt reached the levels of fame he has today. Sinitta has spoken openly about her past love saying, “He was beautiful with the most beautiful body, he was fun, he was young and very sweet.”

Looks like Pitt won’t be getting any angry breakup songs from her.

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