2. Paris Hilton – Randy Spelling
Paris Hilton is no stranger to controversy. So it’s not surprising that when she was 15, she ran into fellow trouble-maker Randy Spelling. Spelling, famous for being the son of successful television producer, Aaron Spelling, was 17 at the time. Spelling stated that the two of them hooked up when they were in the terrible 2006 movie, Pledge This! Spelling also stated that they were together for only two months. During this time, Spelling states that he took her virginity. Hilton’s grandmother actually caught the two together in a hotel room and a week later they had broken up.
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