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6. Chad Michael Murray and Kenzie Dalton

Murray is known for dating his co-stars. So it was no surprise when the One Tree Hill actor fell for an extra on the hit series. A 24-year-old Murray began dating 17-year-old Kenzie Dalton in 2005, following his divorce from Sophia Bush. A year later he proposed, but the two reportedly split in September 2013 after being engaged for seven years.

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