Benson lived in Superior, WI until age 6, before he moved with his family to Milledgeville, GA. In 1988, Benson then moved to Kennesaw, GA. He has two younger sisters and one younger brother. In 1998, while playing for the Nashville Sounds in the minor leagues, he met his future wife, Anna Benson while she was working as a dancer in a local strip club. The Bensons were married in October 1999 (her second marriage, his first), the same year he reached the major leagues. The pitcher and model became a well-known baseball couple during Benson's time in the major leagues. After Anna reported that the couple had had sex in the parking lot of Three Rivers Stadium, an experience they wished to replicate at every major league park, concern developed within the Pirates organization that the "wild-eyed brunette was getting in the way of her husband's fastball..." Her husband dismissed the Pirates treatment of his wife as "a lot of jealousy and a lot of pettiness..."' Anna filed for divorce on March 31, 2006, citing an "irretrievably broken" marriage., but later withdrew the petition. They have had three children together (daughter Haylee, and sons P.J. and Devin James) and are also parenting Anna Benson's daughter from her first marriage (Alyssa Warren). In 2012, Kris served Anna with divorce papers. Benson is now engaged to Brittany Page, daughter of retired professional wrestler Diamond Dallas Page.