Jake agrees to let Dylan fix him up with her best friend Cindy only because he secretly wants to be able to spend more time around Dylan. But when Jake and Cindy agree to join Dylan and Gavin for a romantic weekend, Jake calls on Claire for advice. Meanwhile, Frank and Lucia enlist the help of Penny and Sister Brenda when they have to create a public service announcement for the station.

A road trip bonds Jake and Gavin, who discover they share a youthful dance discipline; chitchat over romance entangles Lucia and Dylan (Ashley Williams).

Apartment-hunting rattles Jake, who makes an ill-timed decision to move in to Dylan's place. Too bad she's moved in with Gavin.

On Halloween, the TV program's cast and staff don disguises for the taping of a theme show---at a costume party in a gay bar.

Jake forces a reluctant Penny to have lunch with Dylan in order to create more harmony in the office, but Jake becomes floored when Dylan tells him to admit he has a crush on someone at work. Meanwhile, Sister Brenda and Frank are at odds over a pocket watch Frank took from their deceased uncle.

Dylan gets upset when her mother (Bess Armstrong) and Gavin clearly do not get along, but things get even more sticky when her mom begins to think Jake would make a better suitor. Meanwhile, Frank has an unfortunate accident with a copy machine.

While Sister Brenda thinks of leaving her convent, Jake gets in hot water when he enrages Dylan by questioning her intelligence. Meanwhile, Claire is offered the role of a guest host on the show.

Jake finds himself in a jam when he falsely leads Dylan and Gavin into thinking that he, like Gavin use to be, was an alcoholic. Elsewhere, Penny ponders what to do when she finds Frank has her under his 'Emergency Call' number.

After a little help from Penny, Jake conspires the perfect gift for Dylan, a poetry book inscribed with his true feelings towards her, but everything goes wrong with Frank issues a present-swapping time. Finally Jake retrieves the book and gives it back to Dylan, telling her it's very important. It seems like he's finally going to get her, but everything goes rye when Gavin finds the inscription. Meanwhile, Claire instructs Frank to build Jake's Christmas present -- a bike, and also finds out about all the pathetic gifts the ex-station manager received in past years.

When Gavin confronts an anxious Jake, revealing to him that Dylan knows of his feelings, he sets up some guidelines for when he's in the hairstylist's presence. Meanwhile, Claire finally gets her dressing room, but also inadvertantly discovers Penny's feelings for her grandson. As Frank ponders his weight, Dylan tries to sort out her feelings about Jake, only to get into a fight with her boyfriend. After Gavin leaves, Dylan pours out her feelings to Frank, whom is in need of a haircut. She tells a tale of a girl named Mee (Mie) who is torn between two men, Davenport and Lake. When Dylan finally confronts Jake, she finds him in an akward position...he's kissing Penny.

After the romantic kiss they shared in the previous episode, co-workers Penny and Jake decide to work out their situation, coming to a final decision -- their relationship will be strictly physical. Meanwhile, Dylan tries to pry out information on Jake and Penny from Frank, who wonders why Gavin and him have barely ever talked. As Dylan continues her quest for answers, unnerving Gavin, Claire becomes involved with a T.V. repairer by the name of Lenny (Tom Poston).

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.

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.

Jake asks Dylan out on a date, but she turns him down claiming that she is not ready to move on until she knows that Gavin is ready. Penny and Jake form a new segment for Good Morning, Miam called Get It On with Gavin, a dating show where Gavin dates a woman on camera and, in the next episode, decides if he will go out on another date with her. All goes well, until the date shows up and is a complete idiot. Jake feeds her lines through an ear-piece on camera so the date won't be a complete waste. Gavin finds out and tells Jake that he just isn't ready to move on, but Jake gives him a few words of encouragement. The next day Gavin makes a move that shocks Dylan and Jake. Meanwhile, Claire gets a phone call saying that an old friend of hers is in the hospital. Frank asks if she wants to see her, but she refuses because of a falling out the two had. When Frank learns about the falling out, he takes Claire to the hospital to visit her old friend. The air is cleared until another

Dylan needs time to think over Gavin's proposal, Claire and Frank can't keep it together during their appearance on a PSA for the influenza shot. Penny tells Jake, "I love you," and then quits. Jake tells Dylan, "I'm in love with You," but things go awry there. Penny and Gavin have dinner together and end up consoling each other. Gavin and Penny kiss. Jake runs after Penny and Dylan runs after Jake.

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.

Gavin shows up for work looking like a mess after being kicked out of Penny's bed in the middle of the night after she thinks he is getting emotionally involved in the relationship. Jake jumps in to keep the show running, but ends up bringing more havoc into the situation. Meanwhile, Dylan calls upon Victoria for help buying a car.