3. Hilary Duff
Even most Disney fans likely didn’t know that Hilary Duff and Shia LaBeouf were a couple for a brief period of time. Duff will always be known as the main character in the Disney teen sitcom Lizzie McGuire, and LaBeouf got his start on the Disney show Even Stevens. Hilary turned into a successful actress, businesswoman and singer, while Shia has had some ups and downs in his career. He had some negative things to say about the Indiana Jones and Transformers movies he starred in, and is known for getting into arguments with celebrities. Duff and LaBeouf only lasted one date, and Shia confirmed that it was the worst date either of them ever had. Hilary hasn’t said much about their “relationship,” which is probably an indication that it wasn’t worth talking about.
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