Tom Selleck and Jillie Mack – 32 Years

Tom Selleck was 38 years old and divorced when he fell for Jillie Mack after watching her perform in the play Cats. He even watched the show numerous times just to catch a glimpse of the young actress and dancer that had captivated his heart. He eventually found the courage to ask her out.

After Jillie finished her contract with the play, she moved to Hawaii where Selleck was filming Magnum P.I. The couple married secretly in 1987; they even had polaroids taken that day to avoid any leaked photos. Later on, they welcomed their daughter, Hanna Margaret in 1988. Selleck currently stars in the show Blue Bloods.