When a cop claims he's having an affair with the Captain's wife, the Captain punches him and subsequently has to attend anger management class.
This episode includes examples of the following tropes:
- Berserk Button: Sharkey hits Stottlemeyer's when he says he's having an affair with his wife.
- Cassandra Truth: Karen tells Leland that she's never met Sharkey before in her life when seeing the other cop face-to-face. Sharkey then starts professing love for her right there...but Monk busts him. He gets his "Eureka!" Moment that Karen is telling the truth and proceeds to tell Leland that Sharkey weaponized the other cop's temper. Regardless, Karen is upset with Leland for not believing her and reveals that she's filed for divorce.
- A Day in the Limelight: For Captain Stottlemeyer.
- Dirty Cop: Sharkey, who is on Karpov's payroll and kills a potential witness again him. When the victim knocks one of Sharkey's teeth out in a fight, he goads Stottlemeyer into punching him in order to cover up the injury.
- Downer Ending: Karen divorces Leland, leaving the latter to bitterly regret their marriage couldn't be saved.
- Doesn't Like Guns: Karen Stottlemeyer. It's only one of the many ways that she and Leland are incompatible, according to Monk.
- Dramatically Missing the Point: When Leland confronts Karen with the photo of the man she was with, Karen says he's a divorce lawyer. Leland incorrectly assumes that she was having an affair with the man and says that he forgives her, and they'll work it out. Karen then hands him a set of freshly filed divorce papers.
- Fatal Flaw: Leland's temper is heavily deconstructed as one of the reasons Karen is divorcing him.
- I Never Said It Was Poison: Monk realises Sharkey knew Karpov because Karpov called Sharkey a sergeant during the lineup, despite the fact that nobody said that he was a sergeant and Sharkey was wearing plain clothes.
- Manipulative Bastard: Sharkey was willing to (further) ruin Leland's marriage by claiming to have slept with Karen in order to trick Leland into contaminating the crime scene and a subsequent lineup. Later, he even tries to gaslight Leland into thinking Karen's denials of sleeping with Sharkey are lies.
- Mythology Gag: At one point, the homeless man Gerald Vengal is reading his mouse Devo a Diagnosis: Murder novel, written by Lee Goldberg. Specifically the fourth book, The Waking Nightmare.
- Nice Job Breaking It, Hero: The Captain screws up the case twice. First by punching Sharkey Jr. thereby contaminating the crime scene then by messing up the line-up by starting a fight with Sharkey again. Fortunately, Monk is able to solve the case anyway. To a lesser extent, his behavior gives Karen the courage to admit that she wants a divorce and doesn't want to reconcile with him.
- Nice Job Fixing It, Villain: Sharkey Jr. eating an apple in the middle of the bullpen is what allows Monk to finally figure out he's the killer.
- Pistol-Whipping: Chicklet is murdered in this fashion, as since the pistol was Sharkey's police weapon, he knew the bullet could be traced to it.
- Police Line Up: Done so that Gerald Vengal can identify the killer. Unfortunately, Leland's anger issues ruin the line-up when he decides to start a fight with one of the cops volunteering.
- Saying Too Much: During the police lineup when Stottlemeyer and Sharkey were brawling, Karpov calls the latter a sergeant. This clues Monk in that the two of them know each other, especially because Sharkey was wearing plain clothes during the lineup.
- Tame His Anger: The anger management session leader attempts to do this with Leland by giving him a yo-yo. He uses it to hit the man he punched to end up in anger management in the first place.
- Verbal Backspace: At one point, Leland angrily and enviously accuses that Karen is indeed cheating on him with Sharkey. Later, Leland tries to pass off his jealous disposition as a sign that "[he] loves his wife." Karen doesn't buy it.
- Wham Episode: Stottlemeyer's marriage falls apart.
- Wham Line: "He's a divorce lawyer." While Karen needs to clarify that she's consulting a divorce lawyer, the viewer realizes immediately what is happening.
- What Does She See in Him?: Monk tells Natalie that the Stottlemeyers' marriage is one he's never understood because they don't have anything in common.
- What the Hell, Hero?: Karen gives a quiet and devastated version of this to Leland. She asks him why he would ever believe that she would sleep around and that he wouldn't listen to her telling the truth. Leland responds by confronting her with a photo of her talking to another man. Realizing he's never going to change, Karen responds that the man is a divorce lawyer and hands him a copy of the papers she has filed.
