Monk's childhood crush asks him to investigate the murder of her housekeeper and Monk tries to impress her by solving the case. The episode also includes flashbacks to Monk's high school years where the same crush is framed for a crime she didn't commit.
This Episode contains examples of the following tropes:
- Abusive Parents: Downplayed but the flashbacks show how Monk's mother formally withheld affection because "[he'd] thank [her] later". It's also clear that a lot of his compulsive tendencies were inherited from her.
- Anachronism Stew: In the flashback when Monk is explaining how Jimmy stole the bake sale money, the principal finds a $5 he wrote "good luck" on and holds it up for everyone to see. The enlarged face of Abraham Lincoln on the bill establishes it as a $5 bill produced in 2000
- Cannot Spit It Out: Monk in high school trying to ask his crush to the dance and then again in the present trying to ask her on a date.
- Clear Their Name: In the flashback, Monk investigates the theft of the bake sale money in order to clear Sherry's name.
- Did Not Get the Girl: Monk had a crush on Sherry in the past and still fancies her in the present, but she falls in love with another guy instead.
- Even Evil Has Standards: Michael may have been willing to do anything to stop paying alimony to Sherry, but he never meant for Gladys the maid to be killed in the process.
- Felony Murder: Presumably how Michael ends up being charged with the murder of Gladys. He wasn't in the city when it happened and he didn't intend for her to be killed, but he did hire two men to commit the break-in (a felony) and she died as a direct result of it.
- Flashback B-Plot: In the A-plot, Monk is hired by a childhood friend to investigate a murder, triggering flashbacks to Monk's childhood where he had to help the same friend who's been framed for stealing bake sale money.
- High-School Dance: Monk tries to ask his crush to the upcoming spring fling but gets beaten to it by a classmate
- Kick the Dog: Played with, as a passive aggressive variety. When Michael is being arrested for arranging the robbery, he looks at Sherry and spites her by pointing out that his plan technically worked: he got Sherry and Jimmy together. One gets the feeling he meant to say this to leave a bad taste in Sherry's mouth.
- Meaningless Villain Victory: Michael did succeed in his plan to matchmake his ex-wife Sherry with her old boyfriend Jimmy so he could stop paying alimony, but given that he killed her maid Gladys in the process, he's going to either suffer prison or execution, making his victory pyrrhic.
- Nice Job Fixing It Bully: As Monk is being stuffed into his own locker, he notices that the lock on Sherry's locker (right next to his) hasn't been set to zero as she normally does. This tips him off that the bully had switched her lock with his so he could put the cash box in her locker and frame her for stealing the bake sale money.
- Romantic Runner-Up: Monk, twice, losing the same girl to the same guy in the high school flashback and in the present.
- Sherlock Scan: Whilst looking at a painting of a woman making dinner for her husband, Sherry remarks upon how calming it is. Monk however claims the woman is trying to poison her husband. He knows because he recognizes that the mushroom she's chopping for dinner is a poisonous kind. When Sherry reasons that perhaps it's a mistake, Monk points out that the bruises on her arm suggest the husband beats her and poisoning him is therefore intentional.
- Shipper on Deck: Both Natalie and Stottlemeyer seem to want Monk to succeed in pairing up with Sherry. Unfortunately Sherry falls for her old boyfriend Jimmy.
- Stuffed into a Locker: The bully who stole the bake sale money stuffs Monk into his own locker after Monk accuses him of the theft.