Fresh from her success as a teenage pop sensation, Mandy Moore was moving forward with a few Hollywood pursuits in July 2000 (a freshly signed Neutrogena deal and an advice show on MTV called "Mandy") when she took a break for a photo shoot, where she was being pursued by Wilmer. He asked her out. She said yes, and they had eyes only for each other until 2002, when they split for good. But unfortunately for Mandy, the relationship would resurface courtesy of Howard Stern's show when Wilmer dished all his dirty laundry. And what he said about Mandy really hit below the belt in a big way. The actor claimed he took her virginity, and if that invasion of privacy wasn't enough, he threw some salt into the wound by adding, "It wasn't like warm apple pie." We're not even sure what that means, but Mandy wasn't just shaking her head too; she was pointing her finger. She later would tell Elle that his comments were "utterly tacky, not even true, and it hurt my feelings because I like him."