|Out of universe information|
Dolly Flint was a psychic who became involved with the murder of Katherine Ashcombe.
Regarded by most as a "quack," Dolly was arrested three times by Cpt. Leland Stottlemeyer for fraud. She was also arrested for trespassing and reckless endangerment. The latter offenses were caused in part by a sleep disorder that prompted her to walk in her sleep. She offered her services to the police department 220 times--and failed each time to provide any help.
One day, she awoke to discover she was in her car at the base of a cliff. Nearby was a wrecked car containing the body of Katherine Ashcombe, the missing wife of former Police Commissioner Harry Ashcombe. Dolly immediately called the police and was quick to claim credit for being "lead" by Dolly's spirit to the crash site in her sleep. The crash was quickly ruled an accident, although Adrian Monk remained skeptical. Dolly promptly raised her prices. While Adrian was doubtful about her alleged powers, his nurse/assistant Sharona Fleming was not. She quickly asked for a reading and told Sharona she would meet a new man with an English accent.
Adrian kept questioning Dolly, who became quickly annoyed with his pestering. Dolly finally admitted to Monk in private that she was a fake, though she genuinely believed that she had had a genuine psychic experience with Katherine. Believing Harry Ashcrombe guilty of murdering his wife, Monk convinced Dolly to help him stage a fake murder scene at Ashcrombe's house using Ashcrombe's former girlfriend, Jennie Zeppettelli. During the ruse, she accused Harry of murdering Jennie. The terrified Ashcrombe accused Dolly of being a fake, blurting out that he was the one who drove Dolly to the crash site. This confirmed what Monk had suspected--that he had drugged Dolly there because Katherine's car had been covered in a mudslide and might never have been found had someone not "found" it.