Ned Flanders
Ned is a double widower, having been married to the equally religious Maude. They had two children together; the sheltered and naive Rod and Todd Flanders. In the eleventh season, Maude died an untimely death in a freak accident involving a T-shirt cannon, leaving Flanders alone and grieving. While still married to Maude, Ned married Ginger, while on a drunken bender in Las Vegas. Ginger came to live with Ned and his sons for a brief period following Maude's death in a later episode, but she quickly grew tired of the Flanders' sickly-sweet personalities and fled. Despite his outward nerdishness, Flanders has also been connected romantically with a beautiful Christian-rock singer, Rachel Jordan, movie star Sara Sloane and eventually marrying local teacher Edna Krabappel until she died as well.
Jack Nicholson
He has had a number of high-profile relationships, most notably with Anjelica Huston and Rebecca Broussard, and was married to Sandra Knight from 1962 until their divorce in 1968. Nicholson has five children – one with Knight, two with Broussard (including Lorraine Nicholson), and one each with Susan Anspach and Winnie Hollman.