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 Dylan comes up with a great idea for the show Jake gives her a segment of her own to produce but finds it hard to distinguish himself from a boyfriend and a boss. Meanwhile, Gavin takes a joke from Joni a little too seriously and starts to freak out about his age. As he tries new, youthful approaches to his job, Frank tries his own luck with Hollis, a new girl that gets his attention.

Gavin finds that he has more in common with Victoria than he thought when he bumps into her at his AA meeting and she convinces him to go undercover as an investigative reporter to get a story on national television. Meanwhile, Dylan tries to get old high school pictures from everyone and uncovers that Penny has a secret past that no one knows about.

Jake finds out that Dylan has an ex-husband and tries to keep cool until Gavin reveals who Dylan's ex-husband really is -- and Jake can't get him out of his head. Meanwhile, as Halloween approaches, Penny goes to a costumed wedding reception and brings along Frank, who finds that being in costume has extra benefits when he thinks he's found his very own Southern belle.

Jake and Dylan are excited to spend their first romantic Thanksgiving together but Jake's mother, Judy, has other plans and decides that Jake and Dylan should come over for Thanksgiving instead. With the rest of the staff home for the holiday, Frank is left in charge of the station temporarily.

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.

It's zoo week on Good Morning Miami, and guest Erika, a local zooligist is on the show. Meanwhile, Frank decides it's time to ""retire his heart"" and end his dating days, but Jake soon tricks him on a date with Erika. After Frank leaves the table to buy Erika a gift, she leaves because she thinks Frank is weird. At the same time, Penny is trying to score free coffee by stealing the punch card puncher, and Gavin tries to get in on it too, only to abuse the free stuff and get caught. As a result of Penny telling the manager, she is rewarded with free coffee and baked goods for one year. Frank goes to get Erika back, and Jake shows up and tells him what happened. Frank feels very betrayed, but Jake sweet talks his way out of it.

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.

Jake wants to buy new computers for the station, so everyone cuts corners to save up. He asks Victoria for the money, but she doesn't do much about it, so he ends up going to the Sunbright Media Group president, who does give him the money. Victoria becomes upset, so she makes everyone work in the basement instead of the office, because Jake made the president of Sunbright think she wasn't doing her job. To make it up, Jake flies the president out to sing on the show. It turns out with good ratings, and Jake says it was Victoria's idea. Jake realizes Victoria isn't so evil after all when she lets them return to their original offices.

Victoria is fired from her position as WWEN's manager, but she refuses to leave. But when Jake uncovers something from her past, she may have to change her decision.

When the office staffers are drug tested, Dylan finds out that she is pregnant. Although he is surprised, Jake decides to ask her to marry him. Unfortunately, they find out the test result was a mistake before he can propose. Meanwhile, Frank befriends a kindly old lady in the coffee shop. Skeptical Penny tries to warn him that she seems like a scam artist, but even she becomes a victim eventually. Also, Frank is flattered to receive obsessive fan letters from a woman—until he finds out it's the same conniving old lady.

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.

Everyone in the office except Dylan finds out about Jake's failed plan to propose marriage to her. While working on a show about teens and sex—during which he is questioned on his relationship—Jake concludes that he and Dylan are not right for each other. Meanwhile, Frank reveals the secret to Dylan, who is excited to marry Jake. Unfortunately, he misinterprets everything and breaks up with Dylan instead. Also, Gavin brings in a sex tape he made with Penny a while ago, intending to erase it, but Frank thinks it's a tape of a TV show and brings it home to watch with his mom.

Dylan feels that Jake should take some time away from her to consider whether or not he really wants to marry her.

Dylan and Jake want a small, classy wedding, but they agree to get married on the show to boost ratings. The wedding becomes such a spectacle that they run out at the last minute.