The mayor sends Monk to the scene of a double homicide: a lawyer, Lou Pratt, and his assistant. The police, however, are confident they've already found the culprit, a client of Pratt's called Grayson with hundreds of dollars worth of reason to hold a grudge. Monk is suspicious, but he finds his attention distracted by Grayson's neighbor, Monica Waters, a woman who looks strikingly like Trudy. But soon Grayson turns up dead in Monica's garage. Is Monk's new interest hiding a dark secret?
This episode includes examples of the following tropes:
- Acquitted Too Late: Grayson is the primary suspect in the early investigations, thanks to his file being burned. Stottlemeyer drops him off the suspect list when he's found dead in Monica's garage.
- Alone with the Psycho: Subverted; Monk goes to stay the night at Monica's house because she's scared of being alone with everything going on. Then Disher finds evidence that suggests she murdered her husband and hid the body under the garage, and Stottlemeyer calls Monk to warn him. It turns out the "evidence" has a perfectly innocent explanation.
- Bad Liar: In Monk's dreams, when Monk denies he has feelings for Monica, the good-natured Trudy affectionately points out he's a wonderful detective and a terrible liar.
- When Stottlemeyer calls Monk during dinner with Monica and warns him that her husband disappeared under mysterious circumstances, Monk tries to cover by saying it was Sharona, informing him that Benjy just got the lead in the school play, a musical version of Gandhi.
- Big Secret: The reason Monica's husband suddenly went missing is that he was suffering from schizophrenia, and two years ago, he went to a private clinic in Zurich. Monk doesn't find this out until he asks Monica if she's guilty of the murder. They wanted to keep the news from his family.
- Blunt "Yes":Monk: It doesn't make sense.
Stottlemeyer: Does everything have to make sense, Monk?
Monk: Well... yeah, it kinda does. - Chekhov's Gunman: The elderly man and his younger escort who appear at Pratt's funeral. Initially, they just appear to be background characters. However, it turns out the young man is the killer of the week and the older man's will is the reason all the murders took place.
- Forging the Will: Todd Katterskill knew he'd been cut out of his uncle's will, so he forged one saying he had inherited everything and hid it in the files belonging to Pratt, his uncle's lawyer. He killed Pratt to keep him from outing it as a fake and burned a file at random to send the police on a wild goose chase.
- Gibberish of Love: Monk has difficulty talking to Monica.
- I Need to Go Iron My Dog: When Monk invites Monica to see Benjy in the school's musical version of Gandhi, she deadpans, "oh, I believe I'll be having a headache that night."
- Inheritance Murder: A varient. The motive for the main murder is to allow the murderer to replace his uncle's will without anyone realizing it.
- Innocent Bystander: Lou Pratt's assistant is stabbed by the killer when she comes across him killing Lou.
- Kissed Keepsake: Monica gives Monk a kiss goodbye 'on the lips'. Sharona rushes to get him a wipe. Monk pauses a moment, balls up the wipe and tosses it back unused. For the germophobic Monk this is the closest thing to "I will never wash this spot again".
- Not Hyperbole: When Stottlemeyer tells him he's sorry for suspecting Monica, Monk says that he doesn't need to apologize. Stottlemeyer replies that he does — the commissioner ordered him to.
- Red Herring:
- The police suspect Grayson, whose file was the only one burned in the break-in. It turns out he was innocent.
- Stottlemeyer begins to suspect Monica Waters after Grayson is killed in her garage and he finds out she began building the garage immediately after her husband disappeared (suggesting she killed him and hid the body there). She also turns out to be completely innocent.
- Replacement Goldfish: Monica looks similar to Trudy (though Monk's image of Trudy denies the resemblance) and Monk's infatuation with her seems largely to be based on her reminding him of his late, beloved wife. Stottlemeyer thinks it's getting in his way at one point and explicitly tells him she is not Trudy.
- Series Continuity Error: The episode was produced immediately after "Mr. Monk and the Psychic", but before "Mr. Monk Goes to the Carnival", which accounts for the apparent regression of Stottlemeyer and Disher's relationship with Monk.
- Shovel Strike: This is how Grayson is killed when the killer wants to turn focus of the murder investigation back onto Monica.
