When Tony Micelli takes a job as housekeeper for Angela Bower, a successful businesswoman, he and his daughter, Samantha, move into Angela's home. Now Tony and Sam must adjust to their new lives with the Bowers- Angela, her son Jonathan, and her mother, Mona.
At a street carnival in Brooklyn Tony and Angela help at Mrs. Rossini's stand. There Tony also meets Frankie, an old friend. At an charity auction - Tony offers his services for a weekend - she makes the race.After the weekend Tony returns with a proposal from Frankie.
Sam has found a new friend and meets him at the library. But it's the college library - Tony finds this out and assumes that her new friend must be much too old for her. Immediately he goes there and in front of everyone he makes Sam look like a fool. Sam's friend is the 15 year old genius Mason whom Sam just want to use to show off in front of her friends.
Angela and Tony want to pair off Angela's cousin Christy and Tony's friend Lyle. The evening together didn't go as planned, but on the following day the both stand in the doorway announcing their wedding. But unfortunately the wedding coincides with an icehockey game. As the game is more important, Christy angrily cancels the wedding.
Jonathan's grades are at the level where he can skip a grade. He goes from sixth grade to seventh grade. He meets a boy who gets him into trouble and Tony and Angela have to see the principal, concerning Jonathan's behavior.
Sam has no companion for the dance. Tony brings a boy, who's working in the vegetables department in the supermarket, along with him. But with his persuasiveness concerning the protection of birds, Jesse drives away the partner Sam has found inbetween.
For a contribution campaign Tony spends 48 hours on a billboard. This campaign is also heard in Washington and Tony is offered a job as 'Nationwide Coordinator for Special Projects for the Parents' Council'.But Tony refuses - too quick, Angela thinks.
Sam is invited by her grandfather to visit him in Florida. But on her way there, Nick dies. First Sam tries to pay no attention to this but Nick's death, however, left big marks on her.
During a competition Tony injures his leg due to Angela's fault. Of course she now wants to take care of him; but this costs Tony a broken leg. Angela lends him a helping hand in the household, but somehow she can't get anything right for Tony. As a result she starts working again and gets a nurse to look after Tony. But she is much worse than Angela.
Joe, Mrs. Rossini's husband, has cleared off with a woman from the neighborhood. Now Tony should help out at Mrs. Rossini's fish store until they have found a replacement.
Sam and Jesse take Tony's car for a joy ride when delivering food, but she dents the car and when it's time to face Tony, she lies and says a boy, who caused the Bower family trouble in the past, dented the car. But on trial day, Sam confesses what really happened to Tony's car.
Angela has got a new customer - Max Muldoon. Mona and Max fall in love and have a wonderful time together. But then he just quits this relationship. Tony and Angela are quite upset and visit Max at his office. There they find out the reason for the breakup - Catherine-Anne.
Tony takes charge of a teen restaurant. When he throws out a popular student all the other customer follow him. Sam, working there as waitress, gets the order to fire her dad.
In Sam Angela's new neighbor Kelly has found a babysitter for her daughter Melissa. When Tony and Kelly are out once again and Sam wants to go to a concert, Angela takes care of the kid. As she did so, Melissatells Angela that her dad called her once, though he, according to Kelly, is dead. On the basis of the circumstances Angela assumes that Kelly could have abducted Melissa from her father.
Tony's relatives from Italy are coming for a visit and uncle Aldo has a great surprise for Tony: he gives him a 12 hectare piece of the winery. Maurizio, Tony's cousin, has fallen for Angela and wants to marry her.
Sam and Jesse decide to go steady.
To prevent the old school in Brooklyn from being tore down, a benefit concert is organized.There, also 'Tony and the Dreamtones' should be on stage, but due to their continuing disagreements there not, that also caused their breakup years ago. After Tony hears Angela sing, he wants her to join the band on stage for a few songs. But the other's refuse and Tony ultimately quits again.
Tony wants to persuade Sam into going to College. In the course of this, the desire of going to College himself, awakes. But when he has to face the admission test, he chickens out.
Because of a job he has to do Jesse can't go out with Sam and suggests she should go out with Mason instead, who's living there for a short time after he has been thrown out of his room. After a great evening Sam gives Mason a fatal kiss which means the end of the relationship with Jesse after he has learned about it.
When a housekeeper finds out that Tony gets paid more than the other housekeepers on the block, all the housekeepers, even Tony, go on strike.
Sam gets a job as model. This one is a success and other orders follow. But Tony isn't happy about that fact, especially because she's earning a lot of money and with that she's no longer dependent on him.
Max proposes to Mona, but she refuses. When Max' ex-wife shows up, Mona feels threatened by her and, however, accepts the proposal.
Jesse asks Sam to go with him to the prom. But Angela takes to much care of Sam because she wants Sam having the prom night she herself never had. But after all the interferences, Sam refuses to go.
One year has passed and it's again Angela's birthday. In the nights after she has found out about the surprise party Tony gives, she talks in the sleep and confesses that she loves Tony. But waking up all with her 'Tony, Tony' shouts is, however, very embarrassing for her.
In Brooklyn Tony meets an old girlfriend. Her husband challenges Tony for a pool game which Tony should lose to strenghten the self-confidence of his opponent. But this is quite hard thing to do as he would really like to blow away this jerk.