S01E19 — Someone to Watch Over Gavin

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.