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.
The family visit Jonathan's summer camp when his counselor calls Angela to say he is homesick. While there, Angela and Tony realize they both attended camp in the same area many years earlier. Their individual stories of their first kiss seem to coincide, and they soon suspect they may have met each other a long time ago.
After visiting the site in the woods where each remembers from their past, a thunderstorm prevents Tony and Angela from returning to the campsite in time. They end up having to share a room at a cheap hotel. Meanwhile, Mona and the campers tell scary stories and play pranks on the counselor.
Samantha has just begun junior high school, and has little trouble becoming friends with the popular girls. Since they are all from wealthy families, Samantha is afraid they will not like her if they know of her true past, so she tells them that Tony owns Angela's house and is an advertising executive.
The family is thrilled when a recently deceased stranger leaves Mona a sizable chunk of money in his will. Mona soon realizes who the man was, and suddenly doesn't want the money. The man turns out to be a former family friend with whom Mona had an affair many years ago.
Wally, a recently dumped friend of Tony's, is down on his luck, so Tony convinces Angela to go out with him. She is not interested in seeing him again, until Mona dates him. Then a mother-daughter rivalry begins for Wally's attention
Michael, Angela's ex-husband, returns to announce he is going to be married again soon, and invites everyone to California for the wedding. Jonathan takes an instant liking to Heather, his father's new wife-to-be, and to the California lifestyle. Michael tells Angela that he thinks their son would have a better life in California, and that he wants custody of Jonathan.
While everyone prepares for the wedding, Angela and Michael plan for a legal battle for custody of Jonathan. Soon, Angela is ready to give up, but a messy incident at the ceremony proves to Michael and Heather that they are not ready to be parents.
After posing for a calendar, Tony becomes the object of a seductive woman's affections. Angela doesn't want him to date her, but her views change when one of the calendar's other stars takes an interest in her.
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.
Nick, Samantha's grandfather, is denied parole from prison, so he breaks out and prepares to run from the law. First, though, he must confront Samantha, who refuses to speak to him for what he is doing.
Recent college graduate Mona is asked to secretly participate in a sting against age discrimination by applying for a job, then getting turned down. But when Angela learns that her mother has this job interview, she pulls some strings to get Mona hired.
A distant relative of Tony's comes to town to meet the man she is to marry through an arranged marriage. Upon learning that the intended groom is a male chauvinist, Tony throws him out of the house and forbids him to marry his cousin. But this infuriates her father, who flies from Italy to confront Tony.
When Samantha needs more money to participate in activities with her basketball team, Angela hires her to work for her on Saturdays. But Samantha soon realizes that, by working weekends, she is missing all the events she wanted money for. So she decides to do a poor job, hoping to get fired.
Angela is teaching a class on advertising, and Tony is one of her students. For the students' first assignment, they are to make a commercial for a laundry detergent. Tony is overbearingly proud of his ad, but Angela despises it and give him an F.
Tony signs up Samantha for ballet lessons. He is pleased when her instructor tells him she has great potential, but the compliment may not have been sincere.
A sitter's last-minute cancellation leaves Samantha to watch Jonathan while Angela and Tony go to a parents' meeting at school. Samantha panics when Jonathan inadvertently tosses a piece of jewelry down the sink drain. Although Tony had told her not to have any guests, the house is soon full of her friends: Chad, a boy who thinks he can retrieve the missing jewelry, and four of Samantha's friends who come to admire Chad. Tony and Angela return home just as the kids are sneaking out.
Jonathan's friend gets him worrying that, one day, Tony may no longer be part of his life. Hoping to ensure against Tony leaving, Jonathan arranges for him and Angela to meet on Valentine's Day at a restaurant for a romantic dinner for two. But they think that the "Mr. Bower" behind this evening is really Michael, Angela's ex-husband.
Tony's poker game has run late, and Angela hurries him to clean up the house in time for her friend who will soon be arriving. Just as his last guest (a raucous Brooklynite) is ready to leave, Angela's friend (a quiet, straight-laced woman) arrives, and the two end up as an item.
Tony is excited about his bowling trophy. But his victory is overshadowed when Angela, who was quite certain she would win an advertising award for which she'd been nominated, comes home empty-handed. Tony suggests that Angela might feel better about her loss if she congratulated the winner.
Tony's campaign for PTA president is clouded by his opponent's mudslinging. He attempts to justify her accusations by explaining some past misunderstandings (this is done through clips of earlier episodes).
A wealthy international client of Angela's sends his daughter to handle his affairs. She takes a liking to Tony, who agrees to be her escort. But Angela soon feels that she forced the woman on Tony, and goes to break them up.
Arrogant, obnoxious neighbor Diane is devastated by her husband's recent decision to leave her for their maid. She temporarily moves in with the Bowers and Micellis, and nobody in the family enjoys her company.
After hearing a colleague from the shoe factory describe his boredom with his life, Mona encourages him to be spontaneous and pursue a new life. He takes her advice a little too far when he leaves his wife and infant in search of Hollywood stardom.
One of Tony's old baseball friends visits and the two end up in a competition to organize a team of players, then play each other. Tony wants to have Angela play for his team, but when he turns out to be a demanding coach, she decides to play for the other team.
Angela had planned a special dinner for five, in honor of Tony and Samantha's two-year anniversary in Connecticut, but Tony is the only one who doesn't have other plans. During the meal, Tony falls ill and is rushed to the hospital in need of surgery. After he has been given sedatives, but just before he falls asleep, he says "I love you" to Angela.