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. Huh?
A former middle school classmate of Adrian, a woman he had a crush on, comes to Monk then asks him to solve this case to give that old lady - whom she employed - 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.