A wealthy widow's young date is murdered, pitting Shawn and Gus against a dirty rotten scoundrel they are convinced trained the victim to be a con artist.
Shawn and Gus show up at a crime scene at a swanky mansion where a young bachelor, Lance, just fell to his death. Lassie doesn't believe it was murder, but Shawn thinks otherwise. He notices that Lance's ankles and arms were not broken, causing him to believe that he didn't try to brace his fall and was therefore dead before his body touched ground.
They all head to Lance's bachelor pad to further investigate. Shawn spies a book called "Killing with Class" written by Clive Prescott, with a personal note from Clive. It turns out Lance was one Clive's most promising students in his "art of gentlemanly seduction" class.
An older woman, Gillian, whose husband recently committed suicide, was dating Lance at the time of his death. Lassiter and Juliet question Gillian. Lassiter thinks Gillian killed both her husband and Lance, and his theory is further validated when they spot Gillian dining with Clive Prescott.
Henry discovers that Prescott's most recent liaison was an extremely wealthy woman who went on vacation with Prescott in South America and mysteriously never returned with him. Shawn and Gus find Gillian and Prescott at the bank and interrupt a financial transaction the two appear to be making. Shawn charms Gillian and arranges a double date – Gillian being Shawn's date and Gillian's friend Jean being Gus's date.