Jake and Dylan discover there is a betting pool in the office for how long their relationship will last. In an attempt to prove their commitment to their skeptics, they decide to have everyone over for dinner to show how happy they are together. Penny and Gavin bring separate dates in hopes of not being branded as a couple. In the end, the only thing they all know for sure is that relationships are not as easy as they seem.

The station's helicopter crashes in the Everglades during a storm and they are forced to communicate their location to Frank live on the air since he accidentally trapped Jake and Penny inside a magic box.

After Frank gets back together with his ex-wife, he begins showing up at work with suspicious bruises. Everyone thinks she's abusing him, until they discover that Frank has been injuring himself with his amateur magic acts, and his ex-wife just wants him to stop attempting them. Meanwhile, when Gavin realizes that he is not popular with the viewers, Dylan advises him to act more naturally during the show. Even though only one fan arrives at his next public appearance, Gavin is glad.

While Dylan and Gavin make another step towards commitment by planning to adopt a dog together, Jake and Penny realize -- after trying to share a romantic evening in his place -- that they can't move forward in their relationship until Jake resolves his feelings towards Dylan. Meanwhile, Frank accuses Claire of stealing clothes and jewelry from her dressing room.

In an attempt to increase the ratings on the show, Jake persuades Gavin to ""tandem skydive"" with an overly enthusiastic Frank -- not realizing that Frank has a hidden agenda. Elsewhere, Jake also tries to reconcile his relationship with Penny when he sees her dating another guy while Claire invites Dylan out for what seems to be an innocent night of dinner and drinks.

To Gavin's disappointment, he finds that he's #100 on ""Miami's Hot One Hundred List,"" and, much to Dylan's dismay, enlists the help of stern agent Roberta Diaz to give his career a boost.

Meanwhile, Penny convinces Jake to transfer her downstairs to work with Frank, who spends his entire day doing absolutely nothing at all. Claire complains of the new poster with her face on it, which annoys Jake, who's attempts to swoon Penny continue to fail.

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.

After a year of waiting, Jake and Dylan finally get to know each other on a more personal note unlike Penny and Gavin who end up swearing off the opposite sex and intimacy. The awkward situation between the four of them grow as they all return back to their work routines. Unfortunately another disturbance has come up, Victoria barges her way in as the new boss and threatens to fire anyone who isn't up to standards. After Jake and Dylan realize they are now together, they have no reason to stay in Miami, and they both decide that moving to New York may be a good idea.

After the rude intrusion of Victoria as the new boss, Dylan and Jake set off for New York to find a new begining. In a faboulous twist of fate, Dylan finds that the Fab Five from ""Queer Eye for the Straight Guy"" have made over their apartment from fashion faux pas to fabulously fantastic. Unfortunately, Jake and Dylan don't stick around long enough to enjoy their new surroundings.

After she takes Jake's vacation to the Bahamas, Victoria and Jake engage in a power struggle involving job perks. Meanwhile, when Gavin struggles with his own problems of losing his investments, he is left to find extra work that isn't considered the most honorable of jobs, including voicing a lame cartoon character. Gavin's problems make Penny realize that she may actually have feelings for him.