Jack agrees to have dinner with Jill, intending to tell him that she can't date him because of her friendship with Elisa, but when a new reporter, Matt Prophet, comes to WNKW, Jack cancels her dinner plans in order to work with Matt. Meanwhile, Barto's grades suffer because he can't stop thinking about his one-night stand with Audrey; Audrey begins to doubt her relationship with Travis; and Mikey attends a singles sminar with Elisa.

When Jill's co-worker Stan takes credit for his idea, Jill challenges him to a boxing match at Mikey's Office Fight Night at the bar. Jack and Matt cover the story of Jill's fight for WNKW and which causes Jill's jealousy to rise. Meanwhile, Barto asks Audrey out to celebrate a good review of her musical and Elisa feels a connection with a stranger she passes on the street.

Jill is sued for breaking up a marriage and Jack begins to doubt her relationship with Matt when Jill insinuates that Jack may not be the only lady in Matt's life. Meanwhile, Audrey frets when Barto starts hanging out with a female study buddy; Elisa continues to hunt for her mystery man; and Mikey gets an unwanted promotion that requires him to fire one of the waitresses.

Jill's suspicions are aroused when he sees Matt with another women, and he contemplates telling Jack. Meanwhile, Jill's tactless girlfriend offends Mikey.

Barto takes Audrey to meet his snobbish parents after she overhears his mother's invitation on the answering machine. Meanwhile, Elisa finally gets to man, and Jack and Jill get stuck in the laundry room, ruining their dates with Matt and Allison.

In the morning, Jack and Jill lie sleeplessly in their respective beds when a passing ice cream truck sets off a loud car alarm. Both of them run out to shut it off, but Jill must finally yank out a wire. The Ice Cream Man is so grateful that he promises to grant Jill his greatest wish. The next day, at Major Toys, Jill's boss announces that he is putting one of Jill's creations, Zantopia, into development. Jill tells the great news to Allison, who focuses on the career implications. Later, Jill becomes concerned when his boss makes changes to the project. Jack understands Jill's disappointment and sympathizes with him, while Allison thinks Jill shouldn't be upset since he is going to be promoted to vice president.

Meanwhile, Jack is deeply in debt. She refuses to let Matt lend her money, choosing instead to work as a waitress at the @ Bar, where Mikey is a bartender. She is a terrible waitress and must quit. She pawns an antique brooch that her grandmother gave her. Matt buys it and g

As Jack ponders Jill's passionate declaration of his feelings for her, she learns Matt has gotten an offer for a job in Washington, D.C.

Jack chooses between Jill and Matt; and Eliza swears to Jonathon that she doesn't want anything for Valentine's Day. Meanwhile, Audrey injures her leg.

Jack, giddy about celebrating her birthday for the first time with Jill, receives a note at work telling her to meet in a hotel room. But she discovers someone else waiting there for her. Meanwhile, Audrey is jealous when Russell's ex stays at their apartment after losing her own place.