Hilarie Burton and Jeffrey Morgan (With a 16-year age gap)
He has guest-starred in several shows, including The Walking Dead, Supernatural, and recently on The Walking Dead as Dean’s father. His connection with Hilarie Burton was the most famous of his love relationships, and it generated the most interest in the press.
They were married for more than a decade before they had children. The 16-year gap in their ages didn’t appear to be a problem for having a kid.