Despite Robert Sherman's story of surprising an intruder who killed his wife, Monk suspects he set up the "intruder" and murdered both of them. The only problem? Sherman and the "intruder" have seemingly never met. Monk remembers seeing them somewhere together, but he can't remember where. Meanwhile, Natalie is dealing with problems in her daughter's love life as Julie becomes involved with a football player.
This episode includes examples of the following tropes:
- Absence of Evidence: In Dewey Jordan's apartment, Monk finds a .22 pistol and ammo concealed in an air duct. The landlord remarks that it wouldn't be unusual for Jordan to have had two guns, but Monk notes there's no ammo for the .38 revolver that he supposedly shot Mrs. Sherman with.
- All Girls Want Bad Boys: Julie's attraction to Clay seems to be like this. Natalie is clearly worried that Clay will take the relationship too far too fast. Additionally, when she and Julie are fighting about it, Julie claims that mothers like Tim (her old boyfriend) because he's "safe".
- Ashes to Crashes: Monk and Natalie accidently knock over the urns containing the victims' cremated remains at the crematorium, leading to them having to figure out who went into which urn and them trying to pass off what happened as a sudden very strong gust of wind.
- Becoming the Mask: A variation. Natalie puts Monk up to telling Julie about the Birds and the Bees. At first, Monk tries to pass off a few seconds of small talk as his version of The Talk. But when he sees Julie is tearfully confused over her choice of dumping Tim for Clay, Monk acts like a true father figure and tells her she doesn't have to rush who she falls in love with.
- Call-Back: "Lovely Rita" says "alleged knife fight, alleged. I love that word", echoing Chris Downey, the gravedigger from "Mr. Monk Vs. The Cobra", who "allegedly stole" a fortune in diamonds from a courier.
- Chekhov's Hobby: It's mentioned more than once throughout the episode that Tim is on the swim team. It comes in useful when Sherman throws the incriminating photos off the pier.
- Conviction by Contradiction: Monk starts to suspect Sherman of being the killer because he only fired one bullet into his wife's "killer" instead of emptying the gun into him, because, of course, every person handles anger and stress the exact same way. He gets more solid evidence when looking through Dewey's apartment. There, he finds a stashed .22 pistol, whereas Sherman's wife was killed with a .38 revolver and there is no ammo for a .38 in the apartment. But even then, it's not like Dewey couldn't have just stolen the .38 or bought it on the black market, as repeat criminals like him have a weird habit of not using guns that are registered to them.
- Dating What Daddy Hates: Discussed regarding Clay; Natalie doesn't like him because instinct tells her that he's not a good guy, compared to Tim. Julie thinks that Natalie doesn't like Clay because Tim was safe. It turns out that Natalie's instincts were right; never doubt a mother.
- A Deadly Affair: Implied to be Robert's motive, as he is seen in bed with his secretary, who is the one that hires Clay to seduce Julie and get her to get rid of her t-shirt with Robert and Dewey on it.
- Deceased Fall-Guy Gambit: Rob Sherman, a sports agent, "hires" a petty criminal named Dewey Jordan and lures Dewey to his upscale house to commit an "insurance scam" - faking a burglary then splitting the profit. However, it turns out that Sherman is actually using Dewey as a fall guy so he can murder his wife and make it look like she was killed by an intruder whom Sherman killed in self-defense. To do so, he shoots Dewey once using a nickel-plated pistol. When his wife comes downstairs to investigate the noise, Sherman shoots and kills her with a revolver, which he places in Dewey's hand. He then twists Dewey's hand and fires a shot at the doorframe with the revolver to get gunpowder residue on the crook's hand, and make it appear that Dewey fired on Sherman so that his death will look like "self-defense".
- Easily Forgiven: Tim forgives Julie for burning their commemorative t-shirt after their breakup. He realized that Sherman was manipulating them via a proxy.
- Evil Gloating: After throwing the photo disks off the pier, Sherman turns to Monk and sneers, "guess you can't win 'em all, Detective, huh?" His gloating lasts less than five seconds, as neither of them notices that Tim is already diving off the pier to save the disks.
- I Always Wanted to Say That: Natalie asks Tim for help when getting the proof that Sherman committed murder. As Monk waits for a search warrant, Tim asks why. She gleefully says that she always wanted to use Monk's catchphrase: "Here's what happened" before going into The Summation.
- It's Personal: For sabotaging his relationship with Julie, Tim gets revenge on Sherman by obtaining the evidence by swimming for it.
- Laser-Guided Karma: For trying to purposefully put a wedge between Julie and Tim, Sherman's efforts to destroy all incriminating evidence are thwarted by Tim himself when the kid applies his diving skills to retrieve said-evidence.
- Meaningful Background Event: A plotpoint; Monk saw Sherman and Jordan together in the background of the photo Julie and Tim had taken. Because it was proof that they had met and could have planned the "break-in", he had to get it out of sight.
- Near-Villain Victory: Sherman's girlfriend gets Julie to break up with Tim, hence getting her to burn the t-shirt with Sherman and Jordan in the background, and Sherman throws the backup photos from the booth off the pier. Presumably, Sherman would have won if Tim hadn't been on the swim team and if Natalie hadn't taken the courtesy to inform him about the plot.
- Properly Paranoid: Natalie's Mama Bear instincts ended up being correct that Clay was no good for Julie. They find out that a random woman paid Clay, saying she was Julie's aunt, to break up Tim and Julie and he was keeping a girlfriend on the side. Tim takes it well when Natalie explains that Sherman's girlfriend was playing them all for patsies.
- Punch-Clock Villain: Clay was only hired to become Julie's new boyfriend.
- Reverse Whodunnit: The episode is probably one of the closest things to a Monk version of a Columbo episode in that we are introduced to Rob Sherman, see how Sherman kills his wife and a hired accomplice and makes it look like the killed burglar shot her, and see him stage the scene, like a Columbo episode would do it. So the episode is Monk first proving that the murder was staged, then trying to find evidence to prove that Sherman and his accomplice have met.
- Sexy Secretary: Allison Clark, Robert Sherman's secretary. He was having an affair with her and she knew of his plot.
- Shipper on Deck: Natalie clearly has a better opinion on Tim that she allows him to get together with Julie, which contrasts her Properly Paranoid attitude toward Clay.
- Skewed Priorities: Sherman's wife was murdered the previous night, but he makes a point of telling Monk, Stottlemeyer, and Randy to wipe their feet before they enter the house and not soil his expensive rug. The fact that Dewey Jordan's shoes are clean, indicating he did the same before "breaking" into the house, is Monk's first clue that he and Sherman planned it together.
- Stating the Simple Solution: Tim mentions, on hearing The Summation, that they don't need the backup copies from the photobooth. If Julie donated her t-shirt as evidence then Sherman is caught. Natalie sadly says the problem is that Julie burned the shirt, so they have to go with Plan B.
- The Talk: Natalie asks Adrian to give it to Julie. At first Monk just tries to phone it in, but Julie breaks down crying, admitting how confused she is - she's powerfully attracted to Clay, but isn't sure how to describe what she's feeling, so he talks about how much Trudy meant to him.
