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Famous American singer, actor and fashion icon Cher dated Tom Cruise in 1985. Tom Cruise was 23 and Cher was 39 back then. Cher dished about her romance with Tom Cruise in an interview with Oprah in 2008. Back then Tom was still getting used to stardom, “He was shy,” she said. “He said he felt like such a boob in school and nobody talked to him.., It could have been a great big romance, because I was crazy for him.”
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