Randy's mother has remarried to a much younger man, and they're honeymooning at a marriage retreat. Finding this strange enough to warrant investigation, Monk and Sharona go undercover as a married couple at the retreat, and find out that Mrs. Disher's new husband is hiding a dark secret.
This episode includes examples of the following tropes:
- Artistic License History: Monk notices that one antique map in Dalton's store is probably a phony because of it featuring West Virginia, saying it became a state after the Civil War. West Virginia actually became a state in 1863, during the Civil War.
- Bad "Bad Acting": Monk and Sharona act like a couple with bad marriage problems to get into a marriage therapy clinic (Monk being the cowardly mop salesman and Sharona being his alcoholic wife), and do such a terrible job of it that the couple's therapist is relieved to hear they aren't married.
- Buried Alive: A variation; the antagonist causes a cave-in while Sharona and Monk are exploring in a cave on the property, blocking the cave entrance. They manage to escape (because they still had cell service), although the experience freaks Monk out.
- Celebrity Paradox: The episode guest-stars Nestor Carbonell as an antiques dealer scheming to locate a prospector's long-hidden stash of gold. In the novel Mr. Monk and the Dirty Cop, Natalie makes a reference to The Dark Knight at one point, a movie in which Nestor Carbonell plays Gotham City mayor Anthony Garcia.
- Drinking on Duty: Randy does it in the beginning. However, it becomes apparent that Randy doesn't usually do this, and had a pretty justifiable excuse for doing so, as he is shocked that his mother Maria has not only dated, but also married, Dalton Padron, a guy who is significantly younger than her, and she isn't even rich, but they are spending their honeymoon at a marriage counseling place. It is bizarre enough to hire Monk and Sharona to investigate and eventually get a fake marriage in order to do some sleuthing at the mansion.
- Greater-Scope Villain: Joshua Skinner, who murdered his mining partner and hid their stash of gold. By the time of the episode, he's already been dead for almost a century. This is driven home when Monk's summation isn't about the murder Padron committed, but rather how Skinner hid the gold.
- Handy Cuffs: Dalton Padron is able to grab the sheriff's gun because he was cuffed with his hands in front of him.
- History Repeats: In 1849, prospector Joshua Skinner murdered his partner Gully Watson so that he could have all of the gold they'd found together. In 2004, Dalton Padron murders his partner Raymond Tolliver after the latter showed him Joshua's letter confessing to the deed.
- Immediate Self-Contradiction: Played for Laughs. As Sharona and Monk prepare to leave at the end of the episode, the marriage counselor encourages them not to give up on their relationship. When they tell her that the marriage was fake, it greatly puts her mind at ease and she tells them not to get married.
- Kick the Dog: When Randy's mother tries to rekindle her relationship with Dalton by suggesting sex, he coldly rebuffs her, saying she's just "embarrassing herself". Poor thing cries her eyes out in the bathroom.
- "Not Important to This Episode" Camp: Stottlemeyer is absent, allowing Randy to get a bit more focus.
- Obfuscating Insanity: Skinner wrote everything he could write into those journals, even if what he wrote sounded crazy and overly detailed, so he could use up as much Gold-Ink in them as he could.
- Parents in Distress: Padron marries Mrs. Disher as a cover to get into the retreat. Unfortunately for him, her son becomes suspicious and calls in the force's greatest detective. Then he finds the body of Padron's partner. As Dalton tries to escape, he's met by a furious Randy, who demands to know where his mother is.
- Take Me Instead: When Padron gets a gun, one of the husbands at the marriage retreat thinks he'll probably want to take a hostage to help with his escape and volunteers so Padron won't go after his wife. Padron doesn't accept, as his plan for escape involves locking everyone in a closet instead. It still improves the couple's problems, though.