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#1 Jill Schoelen

The first time Brad Pitt proposed to anyone, it was to the actress Jill Schoelen. Schoelen is most recognized for her roles in The Stepfather, Popcorn, and Phantom of The Opera. The two began their romance on in 1989 when the starred in Cutting Class. This was one of Pitt’s first big movies and although he went on to reach stardom she never quite got to his level (not many people do). The flame between the two burned out as quickly as it ignited and three months later they called it quits. Believe it or not Schoelen was actually the one that dumped him, for another man to be precise.

Brad Pitt has opened up about his first engagement saying “She called me up in Los Angeles and was crying on the phone. She was lonely and there was a huge drama. At this point, I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her.” Let’s just say we are sure that the actress regrets her choice.

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