2. Justin Gaston
Knowing what we now know now about Miley Cyrus, it’s really no surprise the nutty singer and actress was involved in a romance with an older guy when she was just 15. Cyrus dated Justin Gaston when he was 20, and the two even met through Cyrus’ father, Billy Ray, who signed off on their relationship. The two later called it quits, and Cryus’ love life has been all over the place ever since.
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