Hilarie Burton and Jeffrey Morgan (With a 16-year age gap)
He has appeared in a variety of shows such as The Walking Dead, Supernatural, and most recently in The Walking Dead as Dean’s father. His relationship with Hilarie Burton was the most well-known of his love relationships, and it was the one that garnered the most attention in the media.
They were together for more than a decade before they got married. When it came to starting a family, the 16-year age difference between them did not appear to be a hindrance.