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.
Tony finally saved up for a solid car for Sam and lovingly equips it with more then ample safety features. She dares not tell him the 'ancient tank' is more of an embarrassment then a dream come true. When it gets stolen, she's 'secretly' delighted but pretends to miss it. When it's returned, Tony finds out the truth as is was parked out of campus sight. Yet he draws a more pragmatic conclusion the the girls expected.
Tony gets a breakfast treat on his first college day, but is too eager for learning too risking being late. Professor Darnell's course public speaking proves quite a challenge, as Tony's Brooklyn accent, vocabulary and grammar constitute the perfect example how never to speak. Despite the merciless humiliation and doubts if posh speech won't harm his relationships or even undermine his personality, Tony toughs it out. His progress and zeal in class impress Darnell enough to be invited to a speeches night on Churchill.
Tony and Angela decide to attend a fraternity party. Little did they know that at the end of the night, they would both be in jail: Angela for her drunk behavior, and Tony for trying to help her escape from an interrogation room.
Tony is surprisingly deeply upset about the loss of trinket keepsakes of his grandfather, who practically raised him when orphaned. Tony still feels guilty for his rascally rebelling then preventing the old man to turn up for his life-long aspired naturalization. Mona suggests and Angela tries a radical solution: a posthumous ceremony with Tony as proxy, if they can convince young judge Matthew Hamilton to be so 'creative'.
The home front feels Agela works too hard and should delegate more. Mona is delighted when some workload is transferred by the recruiting of jack, a talented and charming creative director. Tony however jealously and suspiciously changes his attitude as Jack tends to spend nearly all day with Angela and becomes a regular home guest, even until late at night. When they book in a hotel together, Tony decides to go put an end to their presumed affair, but could have saved himself the trouble.
Jesse Nash is warmly welcomed back by Tony after an ecologist boat trip. However he met a fellow idealist girl and politely dumps selfish Sam, who acts aloof. When Mona gets stoop up too, a week of men-bashing follows. Finally, the 'celicaby converts' go out a for a girls-only-night together, and regain perspective.
Toby wisely forbids Sam to drive to Bonnie's parents's cabin for a weekend in Vermont with an immature sister as chaperon. They go anyway, leaving him worried sick especially as the weather report is stormy. Meanwhile Bonnie gets tired of guilty Sam's recollections of over-protective Tony and bites back that's better then her absent, uninterested dad, which ends up making Sam reconsider.