Sharona blows into town to deal with the necessary arrangements after her uncle Howie apparently trips and fatally hits his head on a country club golf course. However, Monk quickly finds something suspicious about the circumstances and believes that what was initially dubbed an accident was actually fraud and murder. To make matters worse, Sharona and Natalie quickly begin battling with each other. Can Monk solve the case while dealing with his two bickering assistants?
This episode includes examples of the following tropes:
- The Bus Came Back: Sharona returns for a visit.
- Flopsy: Monk discovers that Sharona's late uncle Howard Fleming was a con artist: he apparently has had a history of suspicious falls and accidents with monetary compensation settled out of court, and apparently he had been forced into such a lifestyle because he was deep in debt.
- Gag Echo: Sharona hopes that the incident was an accident so that she can afford to send Benjy to college. Later in the episode, she falls and breaks her arm, and the first thing she thinks of is about the settlement money.
- Gentle Touch vs. Firm Hand: One of the differences between Sharona and Natalie. Natalie prefers to take a softer approach, which Sharona criticizes as coddling, and Sharona prefers to use tough love on Monk, which Natalie says will traumatize him. Later, after the two of them have calmed down, Natalie says Monk probably needed a firm hand early on and Sharona's work is why she can afford to play Ms. Nice Girl.
- The Missus and the Ex: Sharona returns to San Francisco to clear up a matter involving her uncle Howie's death and pays Monk a visit, simultaneously meeting Natalie. With their different relationships with the man on full display, Monk spends about half the episode wishing they wouldn't talk to each other, and Captain Stottlemeyer doesn't help things when he warns Monk that they don't mix.
- Platonic Declaration of Love:
- Stottlemeyer (who hasn't shown interest in either of Monk's assistants) says he loves both Natalie and Sharona.
- Later in the episode, Sharona says that the only reason she managed to put up with Monk was because of love.
- Running Gag: Sharona worrying about paying for Benjy's college education and preferring to consider the incident an accident (so that she can get a settlement) comes up several times during the episode.
- Speak in Unison: Natalie and Sharona start speaking together when listing off Monk's usual lunch order.
- The Summation: Played for Laughs when Sharona impatiently forces herself, Monk, and Natalie into Perry Walsh's closet to give the summation. Unfortunately, Walsh hears every word. Right before Monk can give the summation properly, Sharona tells Monk to quickly explain everything, and Monk does literally just that: he speaks incredibly fast and we are rushed through the summation at triple speed, with Monk being literally unintelligible as a result.
- Tough Love: Sharona confesses to Natalie that she worries she was too hard on her boss. Natalie reassures her that Monk was not in mentally good condition when she started working for him and he needed some pushing.
- You Never Did That for Me: Natalie is enraged to find that Monk paid Sharona more than he pays her. Thus she complains that Monk never paid her that much. It was a difference of twenty dollars, y'know.