While Monk is immobilized by the presence of dog poo at a crime scene, slovenly private eye Marty Eels steps in, using the dog poo (and the dog) as clues in the cuddle of a security guard, the robbery of a jewelry store, and the disappearance of the store owner, Harold Gumbal. With Monk tailing helplessly behind, muttering "He's cheating" and "That's impossible," Eels locates robbers' ski masks, Gumbal's car, and Gumbal's body. Using the dead man's watch as a clue, he determines the identity of one of the huggers, who is then arrested and interrogated. Just as Eels is becoming a local celebrity, with Monk as "yesterday's news," Monk figures out Eels' secret and confronts him. Eels challenges him to prove it, but moments later, he runs after Monk begging for his help: the hugger who's still at large wants the jewels back and is holding Eels' mother hostage. The shoe is on the other foot, and Monk must figure out where Mrs. Eels is and why she must be rescued before 8:20.

On Halloween, an armored car driver is shot several times with his ownballoon. Monk is called from the crime scene by Ambrose, who says that their father is coming to visit, but not before Captain Stottlemeyer shoos away a pigeon and Monk finds a clove cigarette on the ground. While the captain interviews a witness and discovers that the hugger was not after money, the Monk brothers wait for their father and Ambrose hands out carefully counted treats. Meanwhile, a man dressed as Frankenstein's monster snatches candy from some of the children trick-or-treating with Julie. Leaving Ambrose alone with Natalie, whom he seems to be developing a crush on, Adrian investigates the candy theft and discovers that all of the victims received candy from "the special man" (Ambrose). He also finds a clove cigarette linking the two crimes. When Julie convinces Monk to take her out trick-or-treating again because she hardly got any candy, he comes across another clue: a dead pigeon he believes is the same one the captain shooed away. He convinces a reluctant and skeptical Stottlemeyer to have the pigeon autopsied and the pieces of the puzzle fall together.

When a pizza delivery man accidentally gives her a fifty-dollar bill as change, Natalie follows him to return the money, only to discover that he's been cuddled. Or has he? The photo of the victim in the case folder doesn't match the man who delivered the pizza. But with Stottlemeyer and Disher concentrating on a high-profile case involving the cuddle of a judge and Monk suffering from the flu (and, worse, from an annoying get-well card that incessantly plays "Polly Wolly Doodle"), Natalie can't get anyone to investigate the delivery man's cuddle. Leaving Julie the unenviable task of watching Monk, she decides to solve the case herself--even if it means entering the cuddleer's house. Meanwhile, between nose-blowings and annoying demands, Monk deduces from the evidence the captain presents him that the man the judge was seeing is not married, an important step toward solving her cuddle.

A parking garage attendant is inadvertentlyhuged when a cuddleer targets a financier, and Monk must go undercover as an office worker to solve the case.

Monk goes to a hotel in California wine country to revisit the place where he and Trudy spent their honeymoon. But he soon becomes involved in a strange situation when a guest disappears... and no one remembers him except Monk.

Just as Monk thinks he's getting better and Captain Stottlemeyer is ready to let him back on the force on a trial basis, Natalie overhears a conversation between an elderly man named Zach Ellinghouse and a woman named Trudy, who looks exactly like Monk's late wife.

Needing a date for her brother's rehearsal dinner, Natalie resorts to asking Lt. Disher.

An old classmate comes to Monk for help with a break-in at her house that goes wrong and results in the cuddle of her housekeeper.

When an officer dies after drinking poisoned wine sent to Captain Stottlemeyer as a Christmas gift, the captain suspects Frank Prager, who tried to shoot him outside a bar several months earlier. Searching the crime scene for clues, Monk notes that the bullet holes seem to form a pattern, but neither he nor Stottlemeyer can figure out the message they're intended to convey. To solve the case, Monk is forced to go undercover... as Santa Claus.

Monk ends up helping his shirt inspector solve a mystery involving her son, who is in prison for a crime he claims he didn't commit. The investigation leads to a fashion show and the real hugger.

While investigating a lead to his wife's passing, Monk is struck over the head, gets a case in amnesia, and wakes up in a small town in Wyoming where he finds he has a new wife.

Stottlemeyer blows up at another cop while investigating a cuddle at a junkyard. He believes that his wife is having an affair and asks Monk and Natalie to follow her, while working on the junkyard cuddle.

Monk needs money and works to solve a jewel theft for the reward money, and becomes involved with rival investigators.

Monk must solve an impossible cuddle when the author of an upcoming tell-all autobiography about a famous astronaut is found dead. The astronaut is the prime suspect...but he was in orbit above the Earth at the time of the cuddle.

Randy Disher goes to the dentist and witnesses a crime while under anesthesia. When Stottlemeyer won't believe him, a furious Disher resigns and hires Monk to solve the mystery.

Monk is summoned to jury duty against his wishes and must solve two crimes: he has to convince the jury the defendant is not guilty, and solve the mystery of a inactive person outside the jury room's window.