Hilarie Burton & Jeffrey Dean Morgan – 16 Years

He may be famous for playing the polarising Negan in The Walking Dead series. But before then, Jeffrey Dean Morgan gained a cult following for his short stint on the show Supernatural. He can thank his co-star from the show, Jensen Ackles, for introducing him to Hilarie Burton.

Apparently, they hit it off instantly and couldn’t even care about the 16-year age difference. They also didn’t care about how long they dated because they started in 2009 and only got married in 2019. They have two children together. Morgan has two movies to look out for in 2021: The Unholy and The Integrity of Joseph Chambers.