Stottlemeyer proposes to his girlfriend T.K. Jensen, and receives a yes. The happy couple set about making immediate plans for the wedding, but soon Stottlemeyer's work intrudes into his personal life when a series of frightening incidents dog him and T.K., making the bride wonder if she can handle the relationship. As the best man, and the best detective, it's up to Monk to find the answer and save Stottlemeyer's marriage before it's even begun.
This episode includes examples of the following tropes:
- Blackmail Backfire: "Charlie Doyle", the victim of the week, tried blackmailing "Stephanie Briggs" over their shared past as members of eco-terrorist group the Earth Avengers. She shot him during the money exchange.
- Chekhov's Gun: In Stephanie’s first scene she innocuously attempts to make an excuse to take Stottlemeyer’s tuxedo back. The garment bag is where she hid the gun she used to murder Charlie Doyle.
- Chekhov's Gunman: T.K.'s maid of honor, Stephanie Briggs, appears early when T.K. asks her fiance if he can do something about the SFPD arresting her for speeding, and keeps appearing throughout the episode. Monk ultimately realizes she has been sabotaging the wedding to cover up killing the victim of the week.
- Crime After Crime: After shooting Martin Kettering to keep her identity a secret, Stephanie gets pulled over for speeding as she flees the scene. She quickly stashes the gun in Leland's tuxedo bag but due to this being her third speeding offense, she is arrested and the car is impounded. When Leland took the tuxedo bag out of Stephanie's car after getting her released as a favor for T.K., Stephanie knew that she'd be found out once he opened the bag and found the gun. She then starts terrorizing Leland and T.K. to make them call off the wedding.
- Earn Your Happy Ending: Stottlemeyer marries T.K., who declares that a life with him is well worth it. Monk witnesses his best friend getting a happy ending, and gives them the wedding ring, after it's pried out of his hands.
- Eco-Terrorist: The victim Martin Kettering and his killer Stephanie Briggs were once member of an eco-terrorist group known as the Earth Avengers. They went their separate ways after going on the run, only to run into each other again when Stephanie went to a flower shop that Martin was working at. When he tried to blackmail her into giving him money to stay quiet about who she really was, she murdered him.
- Hidden Depths: Randy does really well on the steel drums and guitars. He has certainly gotten better at his hobby.
- It's Personal: Monk at first wants to solve the case as a favor to Stottlemeyer to protect his life. Then he realizes that the sabotage is affecting Stottlemeyer's relationship with T.K. and decides to do whatever he can to make sure the wedding is back on.
- Love Cannot Overcome: Subverted. After the break-in, T.K. starts wondering if she can handle the nastiness involved in being a cop's wife. When Randy's steel drum blows up during the rehearsal, she runs away in terror and cancels the wedding. However, then Natalie opens up to her about her short marriage to Mitch and T.K. decides she wants to marry Stottlemeyer no matter what the issues will be.
- Mood Whiplash: After the proposal, Stottlemeyer is busy whistling and singing right until he sees the corpse… then starts singing again after walking away.
- Noodle Incident: It's revealed that Karen was Leland's second wife, and his first marriage was annulled after only five days, leading the viewer to wonder just exactly led to such a quick termination.
- Shoddy Shindig: Monk is put in charge of organizing Stottlemeyer's stag-do, but unfortunately Adrian's idea of a "fun" bachelor party involves having everyone come over to watch the movie Bachelor Party at his apartment. Monk's OCD also affects the amenities, as he gets everyone a pizza with no "messy" toppings or sauce on it, insists that they use a porta-john instead of his actual toilet and allots for exactly one stubby of beer per guest; when Stottlemeyer works out that they individually only have enough alcohol for everyone to get a very mild buzz, they instead decide give all their beer to Randy and invert the Designated Driver rule by making him the party's "designated drunk". And then the party is broken up when the murderer-of-the-week sets Stottlemeyer's car on fire.
- Sincerity Mode: Stottlemeyer reveals that T.K.'s first name is Trudy, and asks if it's okay that he's marrying a woman with that name. Monk actually tells him it's more than okay because everyone should have a Trudy in their lives. He then starts supporting their relationship because he sees how happy Stottlemeyer is.
- Worst Wedding Ever: Scary events interrupt Stottlemeyer and T.K.'s wedding preparations again and again, from someone breaking into Stottlemeyer's house to T.K. getting a threatening, untraceable phone call, to Stottlemeyer's car going up in flames during his bachelor party. Luckily, Monk eventually figures out who the mystery stalker is, and the wedding goes ahead as planned.
- You Are Worth Hell: Eventually, T.K. tells Stottlemeyer that she doesn't care what danger he gets into as a cop, she wants to be with him. When she realizes her maid of honor is holding Stottlemeyer and Monk hostage, she refuses to back down.
