Dylan becomes upset after hearing about Gavin supposedly receiving a job offer in New York without telling her. As she fuels her anger, Jake is tempted to give his anchorman up without a fight after hearing Dylan might not move to the Big Apple with him. Meanwhile, Penny and Claire get in an auto accident, and both bribe Frank, the only witness, with friendship, hoping that he'll blame the wreck on the other. Later, when Roberta accidentally slips that the job offer in N.Y. was just a scam to get Gavin a raise in his salary, Dylan gets angry and tells him that it's over for good.

Dylan and Gavin's breakup seems to be effecting the entire office. As Dylan mops around, crying constantly, Roberta tries to get Gavin into a new clique. Realizing that the hairstylist that he's been after since day one is now single, Jake plans to sweep her off her feet, but his grandmother Claire forces him to give it three weeks.

As Gavin mopes around being mean to guests on the show, Jake convinces Dylan to go with him to see ""West Side Story,"" but not until he pays visit to Gavin for some bonding. Meanwhile, Frank, after hearing how much Claire hates her birthday, acts as a mole for the newspaper, sending in gossip and other things about the new Good Morning, Miami co-host so she'll forget completely about turning another year older. Gavin soon hears about Jake and Dylan's little date, and plots to spoil their evening of fun by telling them that he needs Jake to be with him tonight. Jake, wanting to go on his first ""date"" with the girl he's been after for so long, pays Penny to watch Gavin so he can still go out with Dylan. But everything backfires when Penny gets drunk and Gavin tells his ex what Jake did.