A burglar sneaks up to a house and breaks in… where the owner greets him. It’s clear that the owner, sports agent Rob Sherman, and the thief, Dewey Jordan, are working together. Dewey steals Sherman’s stuff and the owner then makes an insurance claim. However, as Dewey begins to steal the stuff, Sherman shoots him dead. When Sherman’s wife Pam comes down to investigate the noise, Sherman shoots her with a second gun that he plants on the dead Dewey. He then calls the police.
Stottlemeyer investigates the murders and calls in Monk. While the detective checks the house. Natalie deals with Julie and her boyfriend Tim, who she had to bring along when they were called away from her taking them to school. Monk examines the crime scene and notices some discrepancies in Sherman’s story: the thief carefully wiped his shoes off before stepping on Sherman’s expensive rug, the box Sherman claimed to get his gun out of was carefully closed, the upstairs phone was unplugged so Mrs. Sherman couldn’t call the police, and despite the fact she supposedly claim down to adjust the thermostat because she was cold she didn’t wear her slippers.
Sherman goes outside and after trying to chase away Julie and Tim, notices that Julie is wearing a photo t-shirt they had taken of themselves at the Bay City Pier. Everyone goes back to the police station where a friendly female witness, “Lovely Rita,” interrupts their examination of the case. Monk wonders where he’s seen Sherman and Dewey together before, and notices that Sherman’s one court appearance, for a court case, was on the same day that criminal Dewey was arraigned.
At school, a male student, Clay, approaches Julie and asks her for help in tutoring. She agrees and they make a study date for that night. Monk goes to Mrs. Sherman’s funeral to confront Sherman, but the sports agent points out that it’s more likely Dewey saw him at court and picked him as a like target for burglary. Sherman leaves with his secretary, Allison.
That night Clay flirts with Julie before Natalie hustles him out of the house. After he leaves he calls a woman and tells her that he’s preparing to reel Julie in. The woman is… Allison, who is in bed with Sherman.
The next day Clay invites Julie to a party with college students and the love-smitten girl breaks up with Tim and starts getting rid of all of her stuff from him, including the t-shirt. Monk and Natalie go to Dewey’s apartment and find tickets for Bay City Pier as well as a hidden gun that doesn’t match the one at the murder scene. Wondering why Dewey didn’t take that gun, Monk figure that Sherman set him up but they don’t have any proof.
Natalie asks Monk to talk to Julie as the closest thing to a father figure and role model in her life. She prods Monk into doing it and listens in at the door while he tries to say something comforting to Julie but is clearly doing it for Natalie’s benefit. Monk tries to leave but Julie starts crying and Monk explains how he felt about Trudy as help for how Julie should handle her romance.
While Disher uses the courthouse video to try and confirm that Dewey and Sherman met, Monk and Natalie are picking up his dry-cleaning when they spot Clay kissing another girl. Natalie confronts him and Clay confesses he was paid to date Julie. He shows them the envelope that the payment came in and Monk realizes it’s the same type that Sherman uses. Finally Monk remembers where he saw Sherman and Dewey together.
Monk and Natalie go to the Bay City Pier where Tim works. They spot Sherman and Monk follows him, while Natalie explains to Tim that Dewey and Sherman met at the pier to plan the fake break-in. When Julie and Tim got their picture taken for the t-shirt, the conspirators were in the background. Sherman saw the photo at the house, then had his girlfriend hire Clay to break up Julie and Tim, so Julie would throw out the t-shirt. However, the photo booth clerk will still have the original electronic image files.
Monk follows Sherman to the photo booth where the sports agent attacks the clerk and steals the backup photos. Monk chases him to the pier where they struggle, but Sherman gets free and drops the photos into the ocean. Tim leaps into the water and recovers them, and Sherman is arrested. Julie gives Monk a kiss on the cheek in thanks for his advice, and Monk desperately tries to find a wipe. Natalie warns him that’s one kiss he’ll have to live with.
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