Monk faces a puzzling case when one man is murdered in a parking garage and another, stock advisor Warren Kemp, has his hand broken. Kemp asks Monk to recommend someone to go undercover at his office, and Monk, intrigued by Natalie's descriptions of the repetitious nature of office life, takes the job himself and finds himself surprisingly suited for the position.
This episode includes examples of the following tropes:
- Artistic License – Cars: Monk figures the killer drives a European car because the tire iron left behind is metric, while all the cars in the garage are American. However, the metric and standard sizes of lug nuts are actually interchangeable.
- Bittersweet Ending: The killer is arrested and the company’s business dealings aren’t being leaked anymore. Unfortunately, Monk’s office friends have rejected him because of his refusal to wear rented or worn shoes for a bowling tournament and Natalie’s relationship with Kemp has ended over a misunderstanding.
- Bumbling Dad: Monk talks about a comedy show where the father was always wrong.
- Cassandra Truth: Natalie accuses Kemp of telling the office workers about a personal experience and she doesn’t believe him when he says he didn’t tell anyone. It turns out the killer was spying on Kemp’s office, read Natalie’s lips and shared the story via email to break up Natalie and Kemp.
- Destination Defenestration: Natalie tells Kemp a story about throwing a guy who was harassing one of her friends through a window.
- Did Not Get the Girl: Natalie and Warren Kemp engage in a lot of flirting and seem to be on their way to a potential relationship. Then Natalie finds out about an email that was sent around, spreading a story she told Warren in confidence. Warren tells her he didn't do it, but Natalie doesn't believe him, saying that he was the only person who heard the story. After finding out the truth, she tries to patch things up with him, but he can't get over her not believing him.
- Down to the Last Play: Subverted; the office bowling match comes down to the last frame, with Monk needing three pins to win it for his team. The opposing captain calls Monk on not wearing bowling shoes and insists that he put on a pair. Monk can't bring himself to put on rented or borrowed shoes, so his team forfeits and his coworkers begin to ostracize him.
- Evil Cripple: The killer is a deaf man with a hearing aid who can read lips.
- Failed a Spot Check: Apparently the security team that comes in twice a week to check for listening devices and other such things didn't think a window not too far from the ground of a restaurant could be a security risk.
- Hypocrisy Nod: Monk tells Natalie that one of the people at the office is "obsessed" with bowling, before quickly adding that it's not positive like his obsessiveness.
- Insult Friendly Fire: Monk picks up a toothpick at the crime scene and says the murderer is insecure and always attempting to make people believe he's tougher than he is. Stottlemeyer happens to be chewing a toothpick.
- Irony: One of the office workers tells the undercover Monk that he should be a detective.
- No Name Given: This is the only episode in the series in which we never learn the killer's name.note
- Pillow Silencer: The killer used a pillow over their gun when they murdered Angela.
- Reading Lips: The culprit is able to do so, and used it to spy on Kemp's conversations in order to get inside stock tips. His scheme involved sitting at a certain table in a restaurant where he has a direct view of Kemp's office. The culprit only resorted to committing various crimes as Kemp was either changing his behavior or his office in a way that would have hid his lips.
- Red Herring: Chilton Handy chews toothpicks and competes against Kemp's team at bowling, giving him a motive for breaking Kemp's hand. However, he is not the killer.
- Screaming Woman: When the killer threatens Monk and Natalie with a gun, Natalie screams in his ear at the top of her lungs. The hearing aid he's wearing amplifies her scream to the point of causing physical pain, allowing Monk to grab the gun and hold him off until the police can arrive.
- Stealth Pun: Possibly an unintentional one. The murderer bumped off Angela the decorator because she was planning to put curtains in Warren's office, which would have left the killer unable to read Warren's lips at all. In other words, it would have been curtains for his moneymaking scheme.
- Soul-Crushing Desk Job: Natalie complains about the monotonous nature of office work and compares office workers to drones. Given that Monk likes things the same, this more intrigues than off-puts him.
- Status Quo Is God:
- Poor Monk goes from making so many friends at the office to being ostracized because he wouldn't wear bowling shoes. So he resumes his job as a consultant detective.
- Kemp refuses to continue a relationship with Natalie on the grounds that she didn't instantly trust him when evidence seemed to suggest he lied to her.
- Technically a Smile: Monk does a frozen and very disturbing smile because he's being watched by a killer who can read lips. Natalie tries to get him to stop, and he says anyone looking will just think they're in love.Natalie: You don't look like you're in love! You look like the victim of an industrial accident!
