Tod and Linc are in St. Augustine, Florida, where they are staying and working at the Hotel Ponce De León, Tod as the assistant social director. There, Tod unexpectedly meets up with his best friend and worst enemy from school, both the same person. He is multi-millionaire eccentric Harlan Livingston, III, who is traveling on his yacht. Harlan, who is looking for a wife, has a soft spot in his heart for women who are ill that he can help nurse - the sicker, the better. This attraction opens him up to cons, poor women who pretend to be wealthy and sick in order to access Harlan's wealth. This situation exasperates Harlan's one-year traveling companion, his uncle, Dr. Frank Hillman, a physician and research scientist who is on this one year journey to fulfill the dying request of Harlan's father to look after Harlan in return for a much needed $1 million cash infusion into his New York research clinic. Frank has a long four months left to fulfill that requirement to get the money. Frank and Harlan have been able to get rid of all of Harlan's truly healthy hangers-on, except for three truly healthy "wheelchair-bound" women, Jeanelle, Cindy and Andrea, who have been able to hang on longer than the others as they are working in cahoots with each other. As such, Harlan offers Tod a lucrative one-week job in replacement for his hotel job: act the wealthier man to lure away Jeanelle, Cindy and Andrea. Tod refuses as he has his sights set on another woman at the hotel, Doree Hunter, who in return is attracted to Tod. She too is looking for love, unlike her gold digging mother who is spending their life savings on this two-week trip to help Doree find a wealthy man to marry to get them out of their poverty. Thrown into the mix is Linc, who, initially unknown to Tod, accepts Harlan's offer for Tod by pretending to be wealthy Tod's bodyguard.
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