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Jun 17, 2012 · Kim Kardashian's Biggest Regret: The Sex Tape. In 2003, 23-year-old Kim Kardashian did something she would regret years later: She made a sex tape with her then-boyfriend, musician Ray J. Four years later, the tape was leaked and sold on the Internet. Watch as Kim opens up about the humiliation she felt and how she broke the news to her family.

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