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Burglars enter a house and are surprised by an old lady coming down a
stairs. She heard the noise and came down with a gun. They take it away
from her, wrestle, she falls and is killed. The thieves leave, but
before they do, go to a portrait painting on a wall and spray paint it.
A former middle school classmate of Adrian, a woman he had a crush on when she was that age (13?), comes to Monk then asks him to solve this case to give that old lady - whom she employed in that hose - justice. Monk takes the case.
Through flashbacks, we then get a glimpse of what Monk was like in that awkward age. Actually, thanks to those flashbacks we see Monk solve two cases on this episode: the one when he's in school and the one "live" with the burglars and the painting. Both involve helping the same female.
All in all, more of an insight on the strange and amazing Mr. Monk.
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.
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