Monk doesn't expect much good when Natalie tells him she's set up a private investigator business for him, and his coolness to the idea seems further justified when their only case so far is a fender bender. However, as usual for the detective, more exists to the case than meets the eye.
This episode includes examples of the following tropes:
- Blackmail Backfire: Captain Gibbard blackmails Dr. Bennett for killing Anna and ups the price for his silence after Monk comes around asking questions. Dr. Bennett just kills him when he tries to pull that.
- Cat Up a Tree: Monk is really upset that his and Natalie's first case while operating as an official private investigator is a fender bender involving Linda Fusco's car. He points out that he's a homicide detective and asks, "Okay, what's next? Getting cats out of trees? Chasing jaywalkers?"
- Chekhov's Gun: Captain Gibbard is first seen untangling kelp from his boat propeller and complains about getting it in a specific area of the bay. Monk later sees that same kelp on the anchor of Bennett's yacht, which pins down the location of the missing woman's body.
- Correspondence Course: Monk apparently took one of these on swimming. When he jumps off Bennett's yacht, he actually pulls out the instruction card he got for the course and tries to read it while bobbing in the water.
- Dr. Jerk: Dr. Bennett is quite an asshole on top of being a double murderer.
- Grievous Bottley Harm: Dr. Bennett strikes his mistress Anna Pollard on the head with a champagne bottle. Whether this or drowning in the metal box he locks her in was what killed her is unclear.
- Have You Told Anyone Else?: As Jay gets ready to bring his boat back to shore, he bitterly asks how Anna's husband took the news of their affair. She says she didn't tell him, and this...gives Jay an idea...
- Illness Blanket: After nearly drowning in the bay while escaping the perp of the week, Monk sits bundled up in a blanket as the boat heads back to the marina.
- Insistent Terminology: It's not Miss Fusco or Mrs. Fusco. It's Ms. Fusco. Monk ultimately sidesteps the nomenclature and calls her "Linda."
- Ironic Echo: Throughout the episode, Natalie uses her motto "Leap and a net will appear" to encourage Monk that he should take the risks as a Private Detective. Later, after nearly drowning in the ocean for all his troubles, a traumatized Monk mutters under his breath "Leap and a net will appear, my ass."
- Ironic Name: Jay Bennett has a motor yacht called The Lucky Lady, which he kills his mistress on.
- It Seemed Like a Good Idea at the Time: Natalie thought she was doing a good thing by pushing Monk into the private investigator business. She just didn't anticipate all the difficulties that Monk would go through.
- Minor Crime Reveals Major Plot: A dented car case leads Monk to the murder of a schoolteacher, committed by the same person who dented the car and left an insulting note.
- Noodle Incident: Natalie mentions that she was able to rent out Monk's new office thanks to a bonus she took out after Monk's paycheck from the "Kensington case".
- Not Good with Rejection: Dr. Bennett's reaction to Anna leaving him to go back to her husband is to kill her.
- One Dialogue, Two Conversations: Midway through the episode, Monk and Natalie confront Dr. Bennett about the fender bender, specifically phrasing it as "we know what happened Wednesday morning." The conversation continues for several minutes with Bennett referring to the murder and trying not to incriminate himself and Monk and Natalie referring to the lesser crime and urging him to settle as it's not a big deal.
- Private Detective: The episode centers around Monk being an official one of these rather than a police consultant. It's not for him, to say the least.
- Reverse Whodunnit: Bennett kills Anna Pollard in the teaser, so the only question is when and how he'll be caught.
- "Shaggy Dog" Story: The episode not only shows how ill-suited Monk is to be a private investigator, but to add insult to injury, Stottlemeyer pretty much had all the evidence he needed to actually nab the killer by himself. Monk doesn't even get a "Here's what happened" moment, and his big contribution to the case (where the body is) could have been provided without him having risked his life in the episode's last act.
- Short-Distance Phone Call: Natalie decides to have Monk try out to be in the private investigation market. Monk and Natalie set up in a temporary office. They get bored quickly waiting for a case. In one scene, Natalie is sleeping with her head on the desk when her phone rings, jolting her awake.Natalie Teeger: Adrian Monk Investigations. What is the nature of your problem?Adrian Monk: I'm being kept in a room against my will.Natalie Teeger: You were kidnapped? Oh my gosh, hold on, hold on. [She quickly grabs a pencil from her desk and starts writing down on a piece of paper] Uh, do you know who did it? [The camera slowly pans left to reveal Monk sitting at his desk, holding his receiver in his hand]Adrian Monk: Yes. It's my personal assistant. Her name is Natalie Teeger.[Natalie turns in his direction and glares at him]
- Suspiciously Specific Denial: Stottlemeyer is in his office browsing an online dating site. When Randy walks in, Stottlemeyer quickly covers up the screen with his coat and tries to claim that he was looking at confidential information on a Vice squad operation. Randy then mentions having seen his profile. Stottlemeyer tries to lie his way out of this, but stops mid-sentence and just admits to browsing around in his free time.
- Villain Ball: If Jay Bennett had just paid for the fender bender damage and not left a threatening note on Linda Fusco's car (or, for that matter, written something like "Sorry!" instead of "Go to hell"), he'd likely not have had to kill Bill Gibbard (a witness who would have confirmed that Bennett killed his girlfriend Anna Pollard) and wouldn't have to try to kill Monk because Linda never would've taken her case to Monk.
- Working the Same Case: Monk's first and only case as a private eye, about a fender bender, is actually related to the missing schoolteacher Stottlemeyer and Randy were investigating.
