Karen Stottlemeyer (Glenne Headly) is the environmentally-conscious second ex-wife of Leland Stottlemeyer and mother of their two children, Jarad and Max. Karen and Leland knew each other since childhood. She also films documentaries. She first appeared in Mr. Monk and the Very Very Old Man, where she begged her then-husband to investigate the death of an old man whom she previously did a documentary on, Miles Holling. One of the reasons for their marital troubles was the fact that Stottlemeyer didn't watch her documentary that won a notable mention award. She later appears in Mr. Monk and the Captain's Wife, where she is temporarily put in a coma after being hit by a tow truck in her car; Mr. Monk Gets Fired, where she films a documentary of the San Francisco Police Department; and Mr. Monk and the Captain's Marriage, where Leland believes she is having an affair (the belief being especially fuelled after a hot-shot police officer, Sergeant Sharkey, claimed he had been seeing his wife, which was actually intended to provoke Stottlemeyer to cover his tracks and true allegiances). It is revealed she was actually seeing a divorce lawyer. She has a sister.