 Sam tries to pass off quickly to Diane the fact that he was interviewed for Boston Magazine s article on the 20 Most Eligible Bachelors. Diane is livid. Sam and Diane are close to the breaking point in their relationship and this article may be the nail in the coffin. Sam knows that it will take a highly romantic gesture on his part to placate Diane and to save their relationship. Carla suggests he have a portrait of Diane painted. Cliff knows a renowned painter who lives along his postal route. Phillip Semenko ends up being a temperamental bohemian artiste, where the art is more important than money. Upon meeting, Semenko takes an instant dislike to Neanderthal Sam, and the feeling is mutual. Just as Semenko is about ready to leave the bar, he runs into Diane, of whom he immediately feels the need to paint a portrait. She knows his work and is in awe. When Sam finds out, an argument ensues between Sam and Diane and he threatens to break off their relationship if she goes off with Semenko. Although she concedes to Sam, she ultimately decides to go off with Semenko since she feels that Sam will understand once the painting is completed. Will he understand?