Monk and Natalie arrive at the inn where the Monks honeymooned for an anniversary, only to stumble on another mystery. Larry Zwibell, a fellow guest, disappears overnight and no one will admit he was there.
The episode includes examples of the following tropes:
- Actually Pretty Funny: The sight of a drunk Monk had both Randy and Stottlemeyer highly amused.
- Bitch in Sheep's Clothing: The owner of the hotel is a sweet little old lady, and welcomes Monk like an old friend, especially since he's an annual patron. Then it's revealed she was in on the Gaslighting conspiracy.
- Can't Hold His Liquor: Played with; One sip of alcohol is enough for Monk to feel the need to go to bed early, and get hungover the next morning. However, everyone seems to think the amount he drank was enough for him to hallucinate a guest. Later, Monk drinks a large quantity of wine under the mistaken belief that it's non-alcoholic, and while drinking that much wine that quickly would probably get anybody inebriated, Monk ends up so drunk he can barely stand.
- Chekhov's Gun: A guy who calls himself Larry Zwibell sits at a table, and the guests say that he reeks of aqua velva, such that it smells like he's been swimming in it. Later in the episode, Natalie remarks about how the alcohol tastes funny. The reason? The man's dead body was hidden in the wine cask!
- Dinner Theatre: Part of the backstory in the episode reveals that Monk ruined a murder mystery theater weekend by solving the mystery in the first twelve minutes, causing the organizers to have to refund all the guests.
- Drunken Master: Monk accidentally got drunk and was able to subdue a hitman, and solve a conspiracy involving everyone in a hotel covering up a man's death so they can keep his money.
- Gaslighting: What the people at the inn do to Monk to make him think the man he met the previous night was a hallucination.
- I Ate WHAT?!:
- Monk is disgusted when he learns that Trudy's favorite wine, which he's been taking sips of in her memory, is the only label produced by the vineyard that they press the old-fashioned way, by stomping on the grapes with their bare feet.
- Natalie is a bit nauseated when she learns that the funny-tasting wine she's been drinking since she arrived actually had a dead man soaking in it, and the funny taste was his aftershave.
- Line-of-Sight Name: The psychiatrist suggests to Natalie that Monk gave his imaginary friend the name "Larry Zwibell" from the signature on a painting in the lobby. Monk himself deduces that the man he spoke to got his alias that way.
- Match Cut: Al Nicoletto kills Rudy in a hotel room, then looks at the postcard Rudy received from Ben Gruber - a picture of the Golden Gate Bridge. As Nicoletto looks at the picture, the camera zooms in on it and immediately turns into the show's title card.
- Old-Fashioned Fruit Stomping: The episode has the detective taking a trip to wine country with Natalie. He enjoys the wine he shared a bottle of with Trudy... until he discovers this is how it's made. One of the winery's staff boasts that they are one of the only wineries that still employ this old-fashioned method, even if it is for just one variety (which happens to be the only kind Monk likes). Monk naturally isn't impressed, and after that, all he can taste is the feet.
- Pulling the Thread: When Al arrives at the winery, he claims that Zwibell is his brother who stole money from the bank he works for. As the group is taking the winery tour, Al asks Monk if he wants a soda to wash out the feet smell. This gets gears turning in Monk's head, as Zwibell referred to soda as "pop". To test things, he says yes, and then tells Al "take your time" in Spanish, which Zwibell spoke fluently while Al has no idea what Monk just said. With this, Monk realizes that Zwibell and Al are so different they couldn't possibly have grown up in the same house.
- Slipping a Mickey: Invoked and Inverted. Monk attempts to do this to Al Nicoletto to extract a confession from him, and also orders for a non-alcoholic beverage (intended for himself) and an alcoholic beverage for Nicoletto. But part of the order gets mixed up, and Monk ends up drunk shortly thereafter.
- Stupid Crooks: For a professional mob hitman, Al really made a stupid mistake in flying under his real name when he is wanted by the FBI.
