- A jealous Diane agrees to have her portrait painted by an arrogant, eccentric artist, even though Sam can't stand the guy and forbids her to do it.
- 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?—Huggo
- Sam cheerfully walks into the bar, happy to have been interviewed for an article in Boston Magazine. The topic? "The 20 Most Eligible Bachelors in Boston." Naturally, the one person who isn't impressed is Diane.
Sam tells Diane that he told the reporter about her, but later on, as the discussion turns to being honest with each other, the truth comes out, and Diane's animosity towards Sam returns.
After talking to his friends, several of them suggest that Sam hire someone to paint a portrait of Diane. Cliff suggests an artist on his postal route, and through some 'creative wording,' gets said artist to appear.
The artist in question is Phillip Semenko, a rather temperamental, opinionated artist who is at first incensed about Cliff lying to get him to come to the bar. His irked persona fumes further when Sam requests that he paint Diane from some photos. Sam's attitude and demeanor cause Phillip to leave the bar...until Diane walks through it, and his artistic curiosity is piqued.
Phillip requests to paint Diane, and she grows flattered, knowing his work and who he is. However, Sam is not at all happy, and threatens to break off their relationship if she goes through with Phillip's offer. Diane claims she won't, and it appears Sam has won.
After Sam heads into the office, Diane then tells Phillip that she actually does want him to paint her. Diane claims that Sam will understand her going against his wishes, but Phillip warns her that he believes what she's doing will harm Diane and Sam's relationship. Even so, Diane wishes to go through with the painting.
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