Alyssa Milano and Brad Penney

Alyssa Milano and Brad Penny Before Milano, who had a handful of hit pop albums in Japan, was designing a line of baseball-inspired fashions, dubbed “Touch,” she was getting an intimate look at the sport courtesy of boyfriend Brad Penny. The pair have since split up, but Milano has been associated in the tabloids with a host of baseball stars, including pitcher Carl Pavano and catcher Russell Martin. (OK, so perhaps it's a stretch counting Milano as a pop singer here, but we needed 10 slides. And here's proof.)
Noah Berger / Associated Press • Carlos Chavez / Los Angeles Times
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