While attending a street fair in Brooklyn, Tony runs into an old flame, whose interest in him is rekindled. Angela fears losing him. She seeks advice from a therapist and is forced to face her feelings for Tony.
Sam makes a date with a 15-year-old college student, without telling Tony. Tony bleeds Sam's friend Julia for what she knows about Sam’s plans. He interrupts her study-date at the college library, and makes a big scene, humiliating Sam.
Angela and Tony play matchmaker with two shy friends of theirs, who hit it off and agree to get married. The wedding is set to take place at Angela’s house, but guests are distracted by a hockey game on TV, causing the wedding plans to be altered.
Jonathan's academic performance accelerates him ahead a grade, and to a new school. He has trouble adjusting at first, but soon makes a friend. The friend is a mumbling troublemaker and Jonathan soon finds himself in trouble too.
Samantha needs a date for her school dance. Tony meets Jesse, an environmentally conscious young man at the market, and brings him home to meet Samantha. But she has found a date, one who decides not to go to the dance after Jesse explains why he is boycotting the event. Despite a rocky start, Samantha and Jesse soon become an item.
In a publicity stunt to encourage children to read, Tony lives on a billboard for 48 hours. The ensuing media attention lands him a very attractive job offer.
Following Nick's death, Tony is concerned when Samantha seems unaffected by the loss of her grandfather.
Tony is confined to a wheelchair after injuries to both legs on separate occasions, both involving Angela. Tony’s impatience with Angela’s help prompts her to hire a nurse, who ends up causing more harm than good.
Mrs. Rossini is devastated after her husband has left her. Tony pitches in to help her run their fish market, but the work, coupled with the search for a capable new employee, soon becomes too much for Tony.
Jesse and Samantha get into a vehicle accident, and they are skeptical to come forward with the truth: that Samantha, who has not yet received her driver's license, was behind the wheel.
One of Angela’s clients is more interested in Mona than in Angela’s presentation. Their romance appears to be going well, but just before they are to take a cruise together, he calls and cancels the trip and the relationship with no explanation. Tony and Angela decide to investigate and are surprised at what they learn.
Tony and Samantha are hired to work at a local fast-food restaurant, a popular hangout for the local teens. When Tony kicks out two of the popular boys, all the other kids follow, leaving the place virtually empty. The disappointed manager instructs Sam to fire Tony, or else Sam will lose her job.
Tony and Angela make friends with a new neighbor, a single mom with a young girl. The closer Tony gets to her, the more suspicious Angela becomes about the woman's secret past.
Some of Tony's relatives visit from Italy. One of his young single cousins develops feelings for Angela, which forces Tony to tell the cousin he and Angela have an undefined relationship and he wants to keep it that way.
Samantha accepts when Jesse asks her to go steady. She soon feels that her dedication to him is taking away from spending time with the other guy in her life: Tony.
The other four members of Tony's high school a-cappella group visit and hope to perform at the school once more before it is destroyed. Angela has a dream to sing with them, but Tony has to change the rules for that to happen.
In an attempt to spark Samantha's interest in pursuing higher education, Tony gets bitten by the academic bug himself, and decides to become a college student. But he begins to have doubts as to whether he is up to the challenge.
While Jesse is away, Sam's friend, Mason, is staying at the Bowers' house. After spending an evening with him, Sam kisses him, and then worries about confessing to Jesse when he returns.
Upon learning Tony's salary, the neighborhood housekeepers feel underpaid and stage a walkout. At first, Tony doesn't want to join them, but Angela's words change his mind.
Sam poses in a photo shoot for one of Angela's campaigns. She considers a career in professional modeling, much to Tony's chagrin.
Max proposes marriage to Mona, but she turns him down, claiming she likes things the way they are. But Max doesn't give up -- he makes a number of attempts to change Mona's mind. She finally does say yes, but only after Max's ex-wife surprises him with a visit. Angela worries that Mona's change of decision is for the wrong reason.
Sam and Jesse's preparations for the upcoming prom are overshadowed by Angela's quest to have everything perfect. She becomes so overbearing that Sam decides she doesn't want to go at all.
Angela is unknowingly waking everyone up at night, sleep-talking about Tony. She overhears a discussion about this the morning after she is heard saying "Tony, I love you". Her embarrassment leads her to not come home, and miss her birthday party.
Tony and Angela run into a girl he knew from the old neighborhood. She is now married to an arrogant, extremely competitive man, who challenges Tony to a serious game of pool.