On their way to a temporary hotel job in St. Augustine, Florida, Tod and Linc are stopped as a drawbridge is raised to allow a yacht to pass through. Tod immediately finds something familiar about the yacht's pilot, and heads over to the other side of the bridge to get a better look. He identifies the man as Harlan Livingston III, a fellow Yale graduate and one of his best friends from school whom he had last seen several years earlier. He decides to try and catch up with him, abandoning Linc (which is a reversal of fortune, as in recent episodes it was Tod who was left holding fort while Linc went off on some xrusade).
Harlan appears to be doing well for himself as he is living the high life and is in the company of various beautiful women. However, his uncle John, a doctor looking after Harlan and with a promise of a million dollar research grant from Harlan Livingston Jr. if he succeeds waiting for him, travels with him and is unamused by his antics, largely because he attracts the wrong type of women...gold diggers pretending to be hurt so Harlan can "nurse" them back to health and they can "convalesce" on his yacht. The most recent example of this, a young brunette named Barbara, has left in a huff after being properly diagnosed with hypochondria, and John warns Harlan that if he doesn't stop doing this and seek help to make him realize his naivete in the whole situation, he will leave him and return to New York.
Tod, meanwhile, is annoyed by Harlan's lifestyle and tells him he needs to stop kidding himself. Just as he is about to leave to head to the hotel, Harlan stops him and offers him a job (the same one he is "performing") for $2000. Tod is uninterested and goes on his way.
As all this is going on, an attractive blonde from New Jersey named Doree and her mother have decided to vacation in the same hotel Tod and Linc are working in. The point of the vacation, despite Doree's objections, is to find her a rich suitor (which the mother believes is the only way she'll be happy). She takes a shining to Tod, who reciprocates to her mother's disgust. What Tod doesn't know is that Harlan has decided to portray him as the millionaire playboy he (Harlan) is, and Linc decides to play along and pretend to be his bodyguard. While Doree's mother (and the three gold diggers Harlan has been taking care of) now approves, Tod is growing increasingly annoyed and starts a pie fight in the hotel restaurant. This only complicates matters further, as instead of losing his job Tod is instead offered a job as the hotel's social director; unbelievably, the pie fight was a rousing success.
Later on, Tod tries to convince Doree that he is not what people are trying to make him out to be and that he really is a humble man who has no material wealth except for the Corvette and $2,200 to his name. Doree seems to believe him, but once again Harlan's tricks come into play and Tod is left embarrassed again.
In his suite that evening, Tod has one more confrontation with Harlan as now his three gold diggers from before are now into him, giving him a pedicure and fanning him with palm leaves. Tod tells Harlan that he is ruining his chance to get with Doree, as he is really falling for her (as is Harlan), and that this whole charade needs to stop. It does, when Harlan finally comes clean to the ladies about Tod and they abandon him as quickly as they latched on.
Meanwhile, desperate to keep her end of the bargain together, Doree's mother accosts Harlan in the hotel and has him check on her, believing there is something wrong with her head. This ends with a final confrontation between all parties involved on Harlan's yacht. Doree reveals that her mother drugged her by putting sedatives in her coffee and Tod and Harlan have one final hashing out which ends when Tod is shoved off the dock into the water. Linc then defends Tod by pushing Harlan off the dock.
The show ends in the hospital, where Harlan is about to undergo a tonsillectomy as his unexpected plunge into the water gave him what his uncle called the worst case of tonsilitis he had ever seen. John tells Harlan that he is tired of his antics and if he pulls another charade like he did before, he would simply leave and go back to New York, feeling the grant was holding him hostage. Although Harlan can't talk, he communicates in writing that the grant had already been given to him by Harlan's father. The reasoning was that they felt he was overworking himself and the whole point of the Florida trip was to give him what they felt was a much needed vacation.
A guilt ridden Doree then comes in and promises she will do anything for him, as she feels responsible for his illness. She agrees to get him a gallon of vanilla ice cream for when he wakes up as it's their shared favorite flavor. Just before he is about to go under anesthesia, he writes one more note to Doree and hands her the notepad as he is wheeled in. The note simply reads: "I love you. Honest!"