3. Chad Michael Murray
One Tree Hill star Chad Michael Murray fell in love with a 17-year-old extra, Kenzie Dalton, on the set of the popular drama. Murray was 24 when he began dating the blonde teen, and he proposed to the high school senior a year later. Although Dalton accepted the proposal, their 7-year engagement finally ended, and the two went their separate ways. Perhaps this was just a wacky phase Murray was going through, because he later married 31-year-old actress Sarah Roemer in 2015.
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