Monk is called upon by old friend Sherry Judd (actress Donna Bullock) to solve a mystery. Monk had a huge crush on her when they were classmates in junior high school. In the present, burglars break into her home when she is not there, and kill the housekeeper, but appear not to have stolen anything. However, on the way out they inexplicably spray paint a mustache and goatee on a prized painting. The police are stumped, so Sherry comes for help to Monk, who demonstrated his detective brilliance to her years earlier.
In flashbacks, we see young Monk's agony as he longs for the teen girl, who is friendly but seems impossibly out of reach. When young Sherry is accused of the theft of the bake sale money, young Monk (actor Grant Rosenmeyer), convinced of Sherry's innocence, tackles what may be his first case, and of course his brilliant insights save her from the clever scheming of the bully who framed her.
Natalie can see that Monk still has feelings for Sherry, and encourages him to make his move, but unfortunately Monk as an adult has as little self-confidence with women as he did as a teen.
Any episode where you get to see Monk as a child is a winner, and this one does not disappoint. His mother (actress Rose Abdoo) does a tidy job of suggesting to the audience where some of Monk's personality quirks come from. Any real fan of Monk will make seeing this episode a top priority.
Monk solves all mysteries, past and present, but loses out on the lady under circumstances eerily similar to what happened in the past.