Monk is back from hiatus after the US Open, we start with a flashback and see a normal house, a neighbor, Sarah McNally, hears a woman’s scream from across the street and a man walking away. She goes over to see the neighbors and finds the couple brutally murdered and the safe opened. At the Seabrook State Penitentiary, Monk is there to speak to the parole board of Max Barton, the killer. He speaks against Barton being released but a lawyer arrives and announces that the federal count has exonerated Barton due to DNA evidence. Mrs. McNally, also present, tries to speak up but it’s too late: Barton is going free.

Monk is at Dr. Kroger's office with Natalie waiting for Harold Krenshaw to finish his meeting. Natalie is reading about the Frisco Fly, a famous masked daredevil. Harold comes out and he and Monk verbally spar. Later, after the meeting, Natalie and Monk head for home. Downtown, the Frisco Fly is climbing a building but falls and when they unmask him it's… Harold.

Monk goes to a murder site where the identifying marks were removed from the unidentifiable car and victim, and is near a patch of poison oak. They're interrupted when Natalie arrives with the news that Harold is the Frisco Fly. They go to the hospital where Harold is basking the in the admiration of the press and his family. Harold asks to talk to Monk privately and talks about his strength of character, and how Monk doesn't have it and never will. Monk refuses to believe that Harold could have done it and they go outside where Harold's newfound fans have gathered to wish him well. Some of them saw Harold fall despite Monk's protestations.

Natalie and a very nervous Monk go up to the roof of the building Harold fell from. Natalie finds Harold's glasses and suggests that Monk should work to overcome his fears. Natalie and Julie try to help him get over even one of his fears but it doesn't go well. A distraught Monk goes to Kroeger who doesn't want to discuss Harold and admits he was just as surprise as Monk was. Monk finally admits that he is giving up.

Disher reports in to Stottlemeyer on a VIN number they've found about the car and they get one piece of identifying evidence. However, they get a call summoning them to Monk's apartment where they find the place in… disarray. Kroeger is there, putting away the knives, as he and Natalie are watching over Monk on a suicide watch.

As the crowds grow outside of Harold's hospital room, Monk wakes up to read an article on Krenshaw. He and Stottlemeyer engage in a battle of wits when Monk refuses to go to the bathroom with Stottlemeyer accompanying him, and Stottlemeyer refuses to let him go on his own.

Harold is at the hospital with his cousin Joey when he's visited by two admiring first-grade students. They give him a present which both Harold and Joey are critical of. Joey gets a call about his uncle, saying he only has a few days left until he dies. Joey lies to Harold about the call and tries to get him involved with a money-making promotional scheme.

Monk and Stottlemeyer still haven't made it to the restroom when Natalie comes in with info from Disher. They go to the apartment of the dead man who it turns out is the real Frisco Fly. Disher reveals the dead man was the driver of the car, and was a circus performer in Hungary. They find reconnaissance photos of all the buildings the Frisco Fly climbed, and Natalie itches because of poison oak. Monk realizes that someone is trying to kill Harold.

At the hospital, Joey is trying to get Harold quietly up to the roof of the hospital. Monk and the others arrive to find Harold gone from his room and Monk figures they're heading for the roof. Joey gets Harold into the Frisco Fly costume and reveals that he plans to kill Harold so he is the only one to inherit their rich uncle's money. Joey prepares to chloroform Harold but Natalie attacks him while a nervous Monk hides by the door. Joey prepares to kill Natalie but Monk runs out to grab him and yells to Harold to get the gun. Harold is frozen in panic and Monk manages to chloroform Joey unconscious. Monk then explains that Joey saw the real Frisco Fly's accident and burned the car, disposing of the body. Then he chloroformed Harold, dragged him up to the roof, put him in the uniform, and tossed Harold off the edge. Harold managed to catch the awning before falling. Harold refuses to say anything so that his son would be proud of him. Harold reluctantly thanks Monk for saving his life and Monk reluctantly accepts it. Harold refuses to give him a reward and then manages to fall off the roof. Fortunately, his parachute opens and the crowd cheers him, and a depressed Monk leaves.

Monk is meeting with Dr. Kroger and discussing his mother's cooking and notices he has a new watch. He quickly concludes Harold Krenshaw gave Kroger a gift, but they're interrupted when Kroger gets a message saying his son didn't get to school. Kroger admits he's at a loss with what to do with him, and Monk offers to help.

Troy and his friends Ridley and Pez are skating in a parking lot when they find a dead man in a car. They find money bags from a bank that was recently robbed, but no money, and Troy finds a treasure map showing where the money is.

Troy and his friends go to Monk and Natalie and spin an unlikely story of the encrypted map being some kind of homework. Eager to help Kroger, Monk agrees to help them and they hit the road, and Monk figures out the first location. They head out in Troy's car while Stottlemeyer investigates the dead man and concludes that skateboarders were there and might know something.

As they head for the treasure location, Troy asks Monk about what his father thinks of him and notes Dr. Kroger is never straight with him, even though he thought he'd be a psychiatrist when he was young. The trail leads to a bar that sells 200 types of beer, matching up with the "200" on the map. At the bank that was robbed, a mildly injured manager Steve Connelly waits for a phone call.

The next clue on the map seems to say "BBQ" but they're interrupted when a cell phone rings: the cell phone that Ridley took from the dead man. Connelly calls and wants to know if "Tony" disposed of the package, but Connelly quickly figures out it's not Tony on the other end. Ridley suggests he cut them in on it but Connelly cuts off as Stottlemeyer and Disher arrive to talk to him. Disher notices he has a picture of "Happy" Jack Connelly, a crook. Stottlemeyer shows him a picture of the dead man who Connelly claims he doesn't recognize.

Monk is unable to find the "BBQ" until they spot a truck with the initials BBQ that match the name of a quarry. They go there and find a big X sticking out of a pile of rock, behind a locked gate. The boys quickly usher Monk and Natalie away and leave, unaware that Connelly has arrived with a shovel.

At his next session, a happy Monk meets with Kroger and drops hints of his solving a case for a friend. Kroger admits his relationship with Troy is going better. Stottlemeyer calls in Monk and Natalie to go over the surveillance tape from the bank robbery. It turns out the dead man in the car died of a heart attack and was one of the two bank robbers on the tape. Monk connects it to Troy and his friends and makes a hasty exit. He finds Tory and his friends and confronts them, and they confess they find the body. Monk gets Troy to agree that they should take the money back to the quarry. However, Monk realizes that the boys only found $5,000 when $2 million was stolen, and wonders why a large red cross marked the spot. As they talk, Connelly returns and uses a crane to bury them both underneath tons of gravel.

The next morning, Monk grows increasingly panicky but still notices that the cell phone taken from the dead man has Jack Connelly's phone number, and the bank phone number, on it. Meanwhile, Natalie tracks down Ridley and Pez after Adrian doesn't show up for the night.

Troy gets Monk to explain that Steve Connelly was the inside man in the robbery and helped his brother Jack set up the whole thing. Jack was shot and died a few hours later, so his brother Steve worked with Tony and wrote out a map showing where to bury Jack. Later when Steve Connelly realized the boys were on to him, he buried the $5,000 and marked with it a big red cross so that Troy and others would find the money and give up.

Natalie brings Stottlemeyer and Disher out to the quarry but they don't find anything. Troy is walking Monk through memories of the weather when he hears the car up above. He turns on the music and cranks the stereo to full volume, and Disher hears the sound. They get Monk and Troy dug up and later Kroger assures them that Troy is okay and plans to study psychology. Monk explains he had a heart-to-heart with Troy and Kroger thanks him for the gift… which Monk wants him to tell Krenshaw about.

A man dressed in black approaches a house, breaks in, and is greeted by the owner, who knows him. The owner, Rob Sherman, tells the would-be burglar to start taking stuff as part of an insurance scam they've agreed to. However, Sherman pulls out two guns, kills the thief with one, and shoots his wife with the other gun when she comes down to investigate. He then wipes off his fingerprints and puts the gun in the burglar's hand and fires one more shot into the doorsill, then calls the police.

The next day Stottlemeyer and Disher investigate and call in Monk, although Disher thinks it's an open-and-shut case. Natalie has to take Julie and her new boyfriend Tim with them since she was going to drop them at school. Monk realizes that the burglar, Dewey Jordan, has clean shoes and wonders why he wiped his feet before coming in. Sherman is concerned about clean feet so no one walks on his expensive rug. Monk goes upstairs and notices the bedroom phone is unplugged, and the box Sherman claims to have taken his gun out is closed and latched. Sherman claimed his wife went downstairs to turn up the heat but didn't wear her slippers.

Outside, Sherman notices Tim and Julie outside and notices Julie is wearing a t-shirt with a photo of them taken at the Bay City pier. The others come outside and Monk wonders why Sherman only fired one shot into the thief instead of shooting repeatedly. Back at headquarters, Monk explains his theory that the whole thing was a set-up, but they keep getting interrupted by a witness to a knife fight, Rita, who pokes holes in the theory. Monk thinks he's seen Sherman and Dewey together somewhere but can't figure out where, and can't come up with a motive for the murder. Sherman has only had one arrest, for a traffic violation. Monk realizes Sherman was in court at the same time Dewey was.

At school Julie and her friend are oohing over guys when a cute boy, Clay, comes over to ask Julie to tutor him in Spanish. Meanwhile, Monk and Natalie go to the funeral where Sherman is burying his wife since he won't take Adrian's calls. After a mishap with the ashes of the deceased, Sherman arrives and Monk points out that he met Dewey in court. However, Sherman claims that it's probably where Dewey saw him and decided to target him for burglary. Sherman leaves with his secretary Ashley.

That night Julie is working with Clay who is clearly interested n Julie. Natalie hustles him out and outside, Clay calls Allison and says that he'll be "reeling" Julie in… and Allison is sleeping with Sherman.

Julie gets word that Clay wants to ask her to a party and Natalie is shocked. Natalie wonders why Julie is breaking up with Tim and burning up his stuff, including the t-shirt. The next day, Monk and Natalie go to Dewey's apartment and Monk notices an air grille with new screws. Natalie is more concerned about Julie's new boyfriend as Monk finds a gun hidden in the vent. Monk wonders why Dewey didn't take that gun, and notes the bullets don't find the gun on Dewey's body. Natalie wants Monk to talk to Julie and he finally gives in. He goes up to Julie's room and stumbles through a birds & bees speech for the benefit of Natalie listening in, then tries to get out. Julie has some serious questions for him and he finally breaks down and talks about his feelings for Trudy.

Disher is following up on Monk's theory and thinks he's found video of Dewey and Sherman meeting at the courthouse. Natalie and Monk are picking up dry cleaning when they spot Clay kissing a girl. Natalie confronts him and Clay reveals that he was paid by someone who claimed to be Natalie's sister to date Julie. Monk recognizes the pay envelope from Sherman's house and the description fits Allison's descriptions.

Monk and Natalie go to Bay City Pier and spot Tim running a booth. Tim is glad to hear Julie is breaking up with Clay, and they spot Sherman and Monk follows him. Natalie explains to Tim that Dewey was at the pier and met with Sherman to discuss their plan. Julie and Tim were there the same day and they got their t-shirt photo taken together, and Sherman and Dewey were in the background. Sherman saw it and had his girlfriend hire Clay to get Julie to break up with him so she'd get rid of the t-shirt. Stottlemeyer is getting a search warrant to check the photo booth copies.

Meanwhile, Monk follows Sherman but gets stranded in a dodge'em car ride long enough for Sherman to get to the photo booth and steal the copies. Monk chases after him to the pier where they struggle over the water. Sherman tosses the photos into the water but Tim leaps into the water and rescues them. Stottlemeyer and Disher haul him away while Julie and Tim get back together. Julie gives Monk a kiss on the cheek and the detective is eager to wipe it off even though Natalie insists he shouldn't.

Monk and Natalie arrive at Stottlemeyer’s office to get some papers signed and finding him talking with his girlfriend Linda over the computer from her bedroom. They are leaving for a vacation in Hawaii on the upcoming weekend and Linda mentions that her partner Sean is showing a house. Sean is showing the house to a couple when a robber bursts in with a shotgun and guns him down, while the couple run away.

The next morning Stottlemeyer meets Linda at her house where he has a city worker removing a hanging branch and a policeman tow away an illegally parked truck. She gets the call that Sean is dead in Malibu. Sean promises to help her find the killer and sends Monk. The police are interrogating the couple, who wonder why they weren’t shot. The wife suggests that the killer was a woman as she was wearing lipstick. They look at the point of entry and it appears that the killer had a key.

Monk talks to Linda who says Sean had a female enemy, Helen Hubbert, who wasn’t happy with a house he sold her. However, Monk begins to suspect Linda, noticing she is the same height as the killer, had a key to the house, is getting Sean’s client, and uses the same lipstick as the killer. They go to Disher who notes that Linda was talking to Stottlemeyer on the computer and couldn’t have possibly been at the crime scene 20 minutes later. When they realize Linda has a motorcycle, they decide to drive across town to see if she could have made it in time. Natalie gets a bike and Monk eventually manages to get on and they’re off… until Monk falls off since he won’t hold on to Natalie.

Eventually they get going but it takes them over an hour. However, Monk notices flowers at the scene that match the lei she was wearing on the webcam when they saw here from Stottlemeyer’s office. They go to give Stottlemeyer the news and he is not happy and believes Monk is jealous.

Stottlemeyer interrogates Helen Hubbert and she admits she hates his guts, and doesn’t have an alibi. Monk listens in and Stottlemeyer gets mad again when Monk tries to intervene. Adrian is convinced that the killer had to have an alibi and since Hubbert doesn’t have one, she must be innocent. Stottlemeyer admits that Linda is the last chance he has but Monk sticks by his deductions.

Natalie gets Linda to show her a house but Stottlemeyer calls and quickly figures out Monk’s absence means he’s busy elsewhere. He tells Linda that Monk suspects her and she begs off and heads back home, where Monk is going over the place. He finds a truck rental bill and a bottle of gun oil. Linda arrives and finds him searching the place, and claims the shotgun was stolen. She asks him up to his bedroom to show him the police report and then tries to seduce him. Monk runs from the house in a panic where Natalie picks him up, and he reveals he know how she did it.

At the police station the next day, Disher is throwing a luau party for Stottlemeyer’s trip and Linda is in attendance. She claims that Monk was crazy and tried to force her to go to bed with him or he’d frame her. Stottlemeyer is immediately skeptical of the claim that Monk would touch any woman. Natalie arrives alone and asks Stottlemeyer and Linda to go into the captain’s office for a surprise present. In the office, Monk is broadcasting over the computer from Linda’s bedroom and says he knows how Linda did it. She turns off the computer and appeals to Stottlemeyer to get her out of there, but they can hear the same Hawaiian music from the impound lot outside. They go outside and find the music coming from a rental truck. Inside is Monk sitting in an exact replica of Linda’s bedroom. Monk explains that Linda rented the truck and duplicated her bedroom inside. On the night of the murder, she parked the truck near the murder site, talked to Stottlemeyer, then went outside and killed Sean. However, the truck was towed, messing up her plan. Monk also noticed that a pen during her transmission rolled when she set it down, but it didn’t roll when he was in her bedroom. On the night of the murder, the truck was on a slant. She appeals to Stottlemeyer who has no choice but to order her arrest.

Stottlemeyer ends up in Hawaii and takes Disher on the second ticket. The captain wonders if Linda ever loved him or if it was a setup from the beginning. Randy misses it and wonders if Linda ever loved Stottlemeyer or if it was a setup from the beginning. Stottlemeyer tosses something into the ocean: an engagement ring.

A woman, Vickie, runs up to the security guard of an estate and tries to get through to a Mr. Magneri. No one answer while behind her a man gets out of a car and comes after her. She tries to give him an envelope and he draws a knife. She runs down the street to the beach and pounds on a trailer for help, but gets no response. She runs out onto what is a nude beach but the man catches and stabs her death.

We start this week with a Rapper by the name of Extra Large givining an interview about the rivalty betweek Rappers. He finishes the interview when his limo arrives to take him to hi next appointment.The limo drives down the road and then the bomb explodes. Extra Large is killed in the explosion and the limo driver is seriously injured.

Monk and Natalie are sychonizing all of Monk’s clocks because daylight savings time. Monk is mad at her though because the clock is now two seconds too late. Monk then gives Natalie flowers for secretaries’ day. Natalie is upset since she thinks of herself as more than a secretary. Murderous (Snoop Dog) arrives at Monk’s house. When he sees Monk resetting his clock he forgets that he didn’t set his clock. Natalie recognizes Murderous and tells him that she has to continually take his music away from her daughter. Murderous tells Monk about what happened to Extra Large. He believes the police will target him because he wrote a song about killing Extra Large and Extra Large used to work for him. He asks for Monk’s help and Monk takes the case. Monk tries to be hip but fails miserably. When Murderous and his assistants leave Monk asks Natalie what just happened. Natalie tells him that he took the case, but Monk thinks he told them he wouldn’t take the case.