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 middle 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. Her actions weren't particularly malicious, 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.
- Bar Brawl: Monk and Natalie trying to apprehend the two vandals in a bar led into an all-out melee with everyone inside getting involved.
- Batman Gambit: The purpose of the break-in was to damage a picture Sherry liked so that she would take it to Jimmy, and they would decide to get married.
- Call-Forward: The flashback shows us the origins of Monk's dependence on wipes (Sherry's idea) and his Catchphrase (coined by a kindly cafeteria lady who sympathizes with his quirk).
- Cannot Spit It Out: Monk in middle 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.
- Chekhov's Gun: Young Monk notices that Sherry sets the dial on her combination lock at 0, which would later convince him of Sherry's innocence. A zero also helps Monk figure out who set up the vandalism on the painting.
- Death by Falling Over: When Gladys confronts the two intruders, it ultimately ends with one of them slamming her head into a table and killing her.
- 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.
- Dramatic Drop: Monk drops a metal cup when Natalie tells him Sherry has come to see him.
- Embarrassing Old Photo: After meeting Sherry, Natalie grabs Monk's junior high school yearbook and looks up Sherry and Monk's old photos. Monk is so mortified that he threatens her with firing, which she ignores, and she and Sherry both coo over how adorable Monk was as a child.
- 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.
- In the flashback, the bully threatens to dip Adrian's clarinet in the toilet, but Jimmy talks him out of it by appealing to his Rolling Stones fanhood: "What would Mick Jagger do?"
- 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.
- Gone Horribly Wrong: All Michael was really trying to do was get his wife together with some other guy she had shown attraction to, albeit for selfish reasons on his part. Now he's going to prison for murder, because the two crooks he hired panicked and killed a woman.
- High-School Dance: Monk tries to ask his crush to the upcoming spring fling but gets beaten to it by a classmate.
- History Repeats: Both as a child and an adult, Monk solves a crime to aid Sherry, the case-breaking clue lies in the way a person uses the number zero, and Jimmy asks Sherry out before Monk can.
- Meaningless Villain Victory: Michael did succeed in his plan to matchmaker 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 go to prison, making his victory pyrrhic.
- Mustache Vandalism: The painting is defaced with glasses, a goatee and a mustache.
- Nice Guy: Jimmy is one of the few kids that stood up for Monk when they were young.
- Nice Job Fixing It, Villain: 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 middle 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.
- Shipper with an Agenda: The whole plot hinges on Sherry's ex-husband trying to set her up with an old flame of hers, hoping they will rekindle their romance, and so he can stop paying her alimony.
- Spanner in the Works: Gladys Aquino to Michael's scheme. He and the Baptiste brothers were under the assumption that the night they were to deface the painting was Gladys's night off, and thus she wasn't supposed to be there.
- 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.
- Stupid Crooks: The Baptiste brothers didn't bother to wear gloves that covered their fingerprints during their break-in... when they already have criminal records.
- The Summation: We get two intercut with each other, one in the past with Monk figuring out how Leo framed Sherry for stealing the bake sale money, and one for how Michael was trying to get Sherry and Jimmy together so he could stop paying her alimony.
