Single dad Tony Micelli and his street smart young daughter Samantha decide to leave the mean streets of their poor neighbourhood for a chance at a better life in Connecticut. Tony happens upon a job offer as a live-in housekeeper for wealthy business woman Angela Bower and her young son by means of her flirtatious mother Mona. He puts his machismo aside and takes the job for the betterment of his daughter and a new ""family"" is formed.

During a trip to Tony's old neighbourhood to find runaway Samantha, Angela must stand up for Tony who is criticized for being a housekeeper. After proclaiming that fighting is no way to resolve a dispute, Angela ends up in a cat fight with the waitress in Tony's old hangout.

Angela comes home from a rowdy birthday party, just as Tony returns home from a police-sponsored demonstration of the effects of alcohol on the mind. Both are in a woozy state, and they end up kissing.

The family go to Mrs. Rossini's apartment for Thanksgiving. Angela is disgusted by the antiquated custom of women waiting on men, hand and foot. She also feels threatened by one of the guests, an attractive young girl who used to know Tony and is interested in him romantically. Meanwhile, Mona appears in the Macy's Thanksgiving Day Parade as one of Santa's elves.

Angela gives a surprise party for Tony because for the first time Angela's agency is in the black and it was Tony who persuaded her to open an agency of her own. As a present the painter Christos should portray Sam. Tony meets him and Christos tells him that a Marie Micelli once took painting lessons at him. This message causes a little crisis for Tony who now thinks he hasn't known his wife well enough.

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.

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.

Mrs. Rossini visits Tony. Accompanying her is her young uncle Al.Al is attending the nearby Beauty College and Tony should take care of him. In the course of this Sam and Al come closer.

Tony gets a new car as birthday present. First his pride forbids to accept it but after some encouragement he, however, decides to keep the car. But selling his Van brings up memories of good old times.

Tony and Angela are apartment-sitting for Mrs. Rossini. After meeting two couples Tony used to be friends with, Angela dreams that she and Tony are married, living in Brooklyn, and expecting a baby.

After researching her family tree, Sam discovers that her great-grandfather, assumed to be deceased, is still alive in Italy. He is flown to Connecticut to meet the family. Tony soon discovers that the man is not who they believe he is.

Al has graduated beauty school, and Tony helps him set up his own salon in Brooklyn. Al's behavior to the customers upsets them, and when Tony explains that Al will never make it unless he changes his ways, Al decides to close the shop.

Tony meets Kathleen's father, who takes him hunting, and later tells him he expects Tony to be the father of his grandchildren. Angela and Mona babysit a child from Tony's old neighborhood.

An older woman from Tony's old neighborhood has fallen ill and wants Tony to be the guardian for her 5-year-old grandson, Billy.

Mona has caught herself another man. But Cliff also falls for Mrs. Rossini who lives at Angela's for some days. Cliff can't decide on one of the both, so a fight for Cliff arises between the two women.

Angela is ready to profess her love for Tony, but her hopes for a romantic anniversary night with him are dashed when he invites her and the whole family to a carnival. A fortune teller tells Tony that he is about to lose the love of his life, but he misses the point. A ride through the Tunnel Of Love changes their relationship.

The death of a friend puts Tony in a mid-life crisis. He has become quite the adventurer, and invites the family on a ski trip. His plan to propose marriage to Angela are thwarted by a series of accidents that consistently plague her. The joy of the proposal is short-lived when Angela turns him down.

Jonathan is looking for a job. A friend of Tony's arranges for Jonathan to work as a ball boy at New York Mets games. A slight mistake during his first game costs him his job -- and the Mets the game.

Tony, Angela, Mona, Jonathan, Mrs. Rossini, and Hank's parents chase after Sam and Hank. They arrive at the chapel before the service began -- Sam did not want to be married without Tony present. Tony is still adamant against the union, but the ceremony goes forward as planned.

Tony has graduated from college and his job search is unfulfilling. He gets a letter from an Iowa university who wants him to teach there. The job sounds perfect for him, but he pretends he is not interested, because it's so far from his home. Angela sees through his facade and convinces him to take the job.

With Tony living in Iowa, Angela and he take turns flying out to visit each other on the weekends. When this plan doesn't work out, Angela agrees to move to Iowa to be with Tony.