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24. 2008: Anne Hathaway & Raffaello Follieri
Anne Hathaway and Italian real estate developer Raffaello Follieri started dating in 2004. The relationship came to a halt in 2008 when Follieri was arrested for defrauding investors out of millions by posing as the Vatican's head of real estate. Supposedly, the FBI even confiscated Hathway's private diaries as part of their raid on Follieri's apartment. He was later sentenced to 4 1/2 years in prison. Talk about shocking.