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:
- 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".
- 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.
- 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.
- 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 he then shot the intruder 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".
- 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 plot point; 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.
- 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, we see how Sherman kills his wife and a hired accomplice and makes it look like the killed burglar shot her, we 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.
- The Talk: Natalie asks Adrian to give it to Julie. At first Monk just tries to phone it in, but he talks about how much Trudy meant to him.
- Your Cheating Heart: Clay was paid by a woman claiming to be Julie's aunt to date Julie. He already had a girlfriend. Julie isn't amused when she finds out, and neither is Tim.