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).

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.

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.