Benson married an FHM model and former stripper named Anna in October 1999. Their marriage has been somewhat infamous because of some comments that Anna made. Anna claimed that the couple enjoyed having sex in the parking lots of major league stadiums and they wanted to do it in every single big league park. Pirates management was upset at these statements and was concerned that the relationship was distracting Kris from pitching well. Anna also stated on The Howard Stern Show that if Kris ever cheated on her, she would sleep with every single player on his team including the manager and batboys. She is one of the stars of the new VH1 reality show Baseball Wives which follows famous former and current partners of baseball players. The show premiered on November 30th, 2011 and was canceled after one season.