S4, E8: Monk and Natalie are cleaning Monk's apartment when they get an unexpected knock on the door. It's Sherry Judd, who went to junior high school with Monk. Intruders have murdered her housekeeper and defaced a painting of her grandmother, and she'd like Monk to investigate. Monk had a big crush on Sherry when they were young, and seeing her again unleashes a flood of memories and emotions. Monk agrees to help her.