After making on-air jokes about the station's management and hookers, Jimmy and Carl get bumped to the graveyard shift. Without consulting Jimmy, Carl announces that they are quitting, so when Jimmy confronts Carl about making the decision without him, the two decide to go their separate ways. But when Jimmy contemplates taking a job in Alaska, Beth decides to intervene.

After Jimmy makes fun of Beth's love of ""An Officer and a Gentleman,"" Beth asks him not to make fun of her and Otis onair. So when actress Jessica Alba (Dark Angel) appears as a guest on Jimmy and Carl's show, her flirtatious behavior becomes more than playful and she makes some advances to Jimmy, not knowing that he's married. Later, Beth finds out that a night of passion with Jimmy was crushed by his fantasies about Jessica Alba, putting Jimmy's relationship to the test.

When Jimmy's old girlfriend Stacey has dinner with Beth and Jimmy, Beth is shocked to learn that her husband had proposed to Stacey several years before. Jimmy's troubles worsen when it is revealed that he gave the same ring to both women. Later, as Jimmy attempts to redeem himself, hip-hop star Marques Houston, a guest on Jimmy and Carl's radio show, offers Jimmy some advice: Propose to Beth again and give her a new diamond ring.

Jimmy's snoring leads to sleepless nights for the whole family -- he repeatedly wakes up Otis, so Beth sends him to sleep in his office. In part to cheer himself up, Jimmy brings home the pinball machine he used to play when he was a teen, which he intends to keep in his office. But he gets a rude awakening when Beth decides to turn his office into Otis' new bedroom.

Looking for some quiet time away from his family, Jimmy volunteers for a rooftop charity Radio-thon as a way to escape for a much-needed vacation, but when he learns that his job has kept him from hearing Otis' first word, ""Da-Da,"" he realizes how much his family means to him... so he goes to unusual lengths to raise enough money to get off the roof. Meanwhile, Beth tries to get Pam to stop flirting with guys since she's now dating Carl.