Letterman has a son, Harry Joseph (born in 2003), with Regina Lasko. Harry is named after Letterman's father.[45] In 2005, police discovered a plot to kidnap Harry Letterman and ransom him for $5 million. Kelly Frank, a house painter who had worked for Letterman, was charged in the conspiracy.[46]
Letterman and Lasko, who had been together since 1986, wed during a quiet courthouse civil ceremony in Choteau, Montana on March 19, 2009.[47] Letterman announced the marriage during the taping of his March 23 show, shortly after congratulating Bruce Willis for getting married the previous week. Letterman told the audience he nearly missed the ceremony because his truck became stuck in mud two miles from their house.[48] The family resides in North Salem, New York, on a 108-acre (44 ha) estate.[49]