Natalie flies to Hawaii for her friend Candace's wedding, expecting a restful week, only to find that her boss followed her. Things quickly go downhill as Monk's tendency to find murder everywhere results in a very morbid vacation.
This episode includes examples of the following tropes:
- Big Brother Is Watching You: It seems that TV medium Dylan Swift is capable of delivering information from peoples' deceased relatives. Monk initially figures out how he really works: he's a cold reader who looks at a person, makes educated guesses, and then uses these guesses to draw broader conclusions. Toward the end, Monk privately tells Natalie a moving story about Trudy and one of her keepsake items. Later, this is used to prove Swift guilty of fraud and murder. After Swift brings the details of the item in question (a security blanket) up on a taping in San Francisco despite not being there for the conversation, Monk reveals that the story was false. Swift had bugged every room of the resort to eavesdrop on potential victims, and killed an elderly woman whose hearing aids were picking up the signals, thus threatening his operation.
- Blackmail Backfire: When Dylan seems to solve Helen Gruber's murder, Martin soon figured out that he was actually the killer, and tried to squeeze him by threatening to reveal that Swift had bugged the rooms. All he got for the effort was his head knocked in.
- Broken Pedestal: Although it took a while, Natalie comes to believe in Swift's ability to talk to the dead after he gave her 'closure' concerning Mitch's death. But after Swift exploits how he "helped Monk" solve Helen Gruber's murder as the two of them working together, Natalie instantly loses all respect for him. She even rescinds her favor to Monk to not expose him as a fraud.
- Busman's Holiday: Monk takes Dioxynl to follow Natalie to Hawaii. After the drug wears off and he's back to being himself, he ruins Natalie's friend's wedding by exposing her groom-to-be as a bigamist, stumbles upon a homicide and drags Natalie along, while trying to find evidence to arrest a television medium for fraud, and solving a rash of mysterious burglaries and car accidents on the way.
- Chekhov's Gun:
- When Monk and Natalie confront Swift after seeing a newspaper article reporting on his involvement in helping solve the murder, he has a fresh blister on one of his hands which he claims he got from making breakfast. As Monk later uncovers, Swift got that blister while he was disposing of Martin Kamakele's body.
- The letter that Monk has notarized and mailed to Captain Stottlemeyer the morning after telling Natalie the story about Trudy's security blanket. It turns out it's a confession that the story was a lie, to be opened after Swift incriminates himself for bugging the hotel rooms.
- Chekhov's Gunman: Dylan Swift is a TV medium that Monk suspects of fraud. Monk is also investigating a double homicide that happens around the same time he and Natalie are in Hawaii. Turns out Swift is also their murderer.
- Cold Reading: Monk and Natalie cross paths with one such notorious psychic named Dylan Swift, who Monk pegs right away as a cold reader, even explaining to Natalie just how he reads people.
- Detective Patsy: TV medium Dylan Swift uses Monk's investigation. He needs to kill a woman named Helen Gruber so that she doesn't find out that Swift has wiretapped an entire hotel to mine information for his shows. He then sees Monk at the resort and decides that if he helps Monk solve the murder, he can get extra publicity for himself. He therefore manipulates Monk into thinking Helen's trophy husband Lance Vaughan is the killer by planting evidence at the scene. However, Monk has been suspicious of Swift from the beginning and figures it out.
- Dramatically Missing the Point: After hearing about Candace's wedding disaster, Natalie's mother feels that it really would've been better if Monk hadn't been there to spoil the whole thing, so when she learned Brian was a liar, it would've been in private. It's not lost on Natalie that if it had been so, Candace would've basically gone into a doomed marriage to a compulsive liar who would've cheated on her and his legal wife.
- Easily Condemned: It doesn't take much to convince his audience that Swift is a fraud and a murderer. When Swift claims that it will take considerable proof to convince the world he's a fake, Stottlemeyer points out that if his fans so easily believed he was psychic without proof, no doubt they'll believe the truth just as easily.
- Feed the Mole: How Monk ultimately ousts Swift as a fraud. Under suspicion that Swift relies on spying on his guests, Monk tells Natalie an anecdote about how Trudy once had a Security Blanket called a "night-night" and was buried with it. But according to the letter he sent to Stottlemeyer ahead of time, this was just something he made up from the top of his head.
- Fresh Clue: Monk comes to the conclusion that Lance murdered Helen Gruber, then faked an alibi by stuffing her in the bungalow fridge overnight to screw with her body temperature. In reality, it was Dylan Swift who did this, but only long enough for evidence of her being in it to be clear.
- Hula and Luaus: Monk and Natalie travel to Kauai. They go to a luau where the main course is supposed to be a pig cooked in a banana-leaf-covered pit, but the workers instead dig up a murder victim's body.
- If I Can't Have You…: The motive for the opening murder. Lyle Douglas had been seeing his nurse Stella Picaro for the past five years. However, instead of leaving his wife for her, Douglas left his wife for a 22 year old swimsuit model. Stella then doctored his medical equipment and poisoned a bottle of iodine to kill the doctor.
- Lost My Appetite: Natalie feels unenthusiastic about the luau after the workers dig up Kamakele's body from the roasting pit, commenting that she may never eat meat again.
- Minor Crime Reveals Major Plot: A slew of hit and run collisions and rental car thefts on Kauai leads to the discovery of a drug trafficking ring, who are staging the incidents so that the cars will be taken to a body shop run by the ringleaders, where the drugs are extracted.
- Mystery Magnet: Natalie sourly lampshades Monk's tendency to find murder wherever he goes:
"...the wedding part I could almost forgive him for, since he saved Candace from marrying a pathological liar and would-be bigamist, but I deeply resented the corpse.
"Most people can go their whole lives without getting involved with a murder. Monk is lucky if he can go outside and get his morning paper off his stoop without tripping over a dead body. Murders happen around him with such astonishing frequency that it's long since gone beyond coincidental and borders on supernatural.
"I guess on some level I knew the moment Monk showed up on the plane that it was inevitable that, one way or another, I'd get dragged into a homicide investigation in Hawaii."
- Phony Psychic: Dylan Swift.
- Peek-a-Boo Corpse: The hotel manager's body is dug up at a luau.
- Pet the Dog: For all of Monk's unwitting tendencies to ruin Natalie's stay in Hawaii, there is one glimmer of kindness that reminds her and the reader that there's a heart underneath all those neuroses. When Natalie gets sunburned and injures herself on some coral, Monk's first instinct is to get his personal first-aid kit and treat both injuries. All the while, he shows genuine concern for Natalie's well-being.
- Shovel Strike: How Martin is killed.
- Shout-Out: A couple to Diagnosis: Murder, which Lee Goldberg worked on before.
- The opening chapter has a heart surgeon poisoned mid-surgery, with the reveal that the patient was the killer by tampering with the doctor's equipment. This was the plot of the Season 4 episode "Physician, Murder Thyself".
- Lt. Ben Kealoha returns from Goldberg's Diagnosis: Murder novel "The Death Merchant".
- Staging the Eavesdrop: Monk figures out that Swift's method of gathering information from members of his audience for the purpose of his show is by having bugged their hotel rooms. In order to get him to incriminate himself, Monk tells Natalie a story about a baby blanket Trudy had. Then Monk has a notarized letter sent to Captain Stottlemeyer, describing the story he told Natalie and affirming that it is false. Upon returning to San Francisco, Monk arranges to appear on Swift's show. When Swift brings up the blanket, and claims to have heard it from Trudy's ghost, he incriminates himself in the bugging, because Monk only told that story to Natalie, and since it's not a true story, Swift can't really have conjured it from the dead.
- Suspect Is Hatless: In a Continuity Nod, Monk tells Natalie about interviewing Warrick Tennyson in "Mr. Monk Takes Manhattan" and his clue about the six-fingered man who hired him to build the bomb that killed Trudy. He then goes on to say that the clue has not been much use, because:
- The six-fingered man could have had the extra finger surgically removed after meeting Tennyson;
- There are a surprising number of individuals born with polydactyly in the U.S., not to mention the rest of the world, so it is still a very large pool in which to search;
- The extra finger could have been a prosthetic disguise worn to mislead or distract Tennyson.
- Vacation Episode: Monk and Natalie go to Hawaii (the latter ostensibly for vacation) and uncover a bunch of criminal activities going on around Kauai.
- Worst Wedding Ever: Natalie attends her friend Candace's wedding, only for Monk to tag along. At the Speak Now or Forever Hold Your Peace moment, he spills that various lies and minor things about the groom indicate that he's already married. This ends in Candace storming out. Natalie tries to take it in stride, despite her frustration; after all, Monk's deductive skills did save her friend from a disingenuous groom.
- Wrongful Accusation Insurance: A variant; Monk, having had a "Eureka!" Moment about an open case, begins cutting open the seat of his and Natalie's rental car. Lt. Kealoha seconds Natalie's question about what he's doing, given that Monk is committing a crime by damaging property. However, it turns out that the seat is stuffed with cocaine. Given that Monk just solved the rash of vehicle thefts, the lieutenant lets the property damage slide.
