The Bowers and Micelli's return to Brooklyn to help Mrs. Rossini at a fair. Tony allows himself to be auctioned, and is 'bought' by Frankie, an old flame. Angela is bummed, and realizes that she loves Tony.
Samantha lies to her father in order to go out with a college guy. While she realizes that this guy - Mason - is a major geek, Tony finds out the truth on Sam's whereabouts and makes a scene. He later tries to apologize by bringing Mason back home.
Tony and Angela set their friends Lyle and Christy up on a blind date. They quickly realize that they would be a terrible couple, and are shocked when they are told that Lyle and Christy are engaged to each other.
Samantha is crushed that she does not have a date for the school prom. Tony, meanwhile, meets Jesse in the supermarket and thinks that he is perfect for his daughter. Samantha, however, can't stand him.
Tony spends 48 hours on a billboard to promote a campaign. Through this, he is offered a major job in Washington, which he quickly refuses. This confuses Angela, who wonders why Tony isn't even considering it.
When Tony tells Samantha that her grandfather Nick Milano has died, he is surprised at how mildly she is taking it. However, it soon becomes clear that she has more trouble dealing with his death than he initially thought.
When Tony is accidentally injured twice due to Angela, she - out of guilt - decides to take care of him. Tony, however, is unsatisfied with Angela's household and hires a nurse, who turns out to be even worse.
Angela's latest possible client Max becomes a close friend of the family, and Mona even considers giving up her bachelorette lifestyle to be with him. Then, one day, he breaks off contact, and leaves Tony to deliver Angela and Mona the bad news.
When other housekeepers of the neighborhood find out how much Tony is earning, they go on a strike until they are given a higher salary. Oddly, Angela encourages Tony to join them, until she learns the downsides about this.
To pay off her debts, Samantha convinces Tony, against his better judgment, to allow her to take a modeling job at Angela's advertisement agency. Soon, she becomes a successful model, with a higher salary than her own father.
Mona rejects a marriage proposal of Max Muldoon; then changes her mind when Max's ex-wife Suzanne shows up, asking him to get back with her. Angela, unaware of Mona's motives, meanwhile wonders why her mother is suddenly so eager to marry.
As soon as Angela hears that Samantha will go to prom with Jesse, she relives a childhood trauma, and does her best to make prom as perfect as possible for Samantha. Sam, however, is fed up with all the preparations, and calls the prom off.
Tony runs into an old girlfriend who has married another man named Tony, who turns out to have lived in Micelli's shadow ever since. To help and boost his ego, Tony (Micelli) organizes a pool match which he intends to lose, but there is one problem: he can't stand the other Tony.