High-strung advertising executive Angela Bower needs a housekeeper, and assistance raising her young son, Jonathan. Macho former athlete Tony Micelli wants to move from Brooklyn, New York, to provide a better life for his pre-teen daughter, Samantha. Although Angela is reluctant at first, her fun-loving mother Mona talks her into hiring Tony as her housekeeper and role model for Jonathan. Despite a rocky start, they all settle into a brand new way of life in Fairfield, Ct.

A sequence of mix-ups results in Tony walking into Angela's bathroom just as she is stepping out of the bathtub. To help her overcome her embarrassment, Mona convinces them to try a psychological exercise.

Having difficulty adjusting to her new suburban life, Samantha runs away, back to her old neighborhood, and Jonathan follows her. Tony and Angela go to Brooklyn to retrieve them. While visiting a bar, one of Tony's former hangouts, Angela gets into a rumble with an obnoxious waitress.

Mona is dating a fellow student many years her junior, much to Angela's dismay. A fight between Angela and Mona ensues when the man gives Mona his pin.

Tony visits Angela at the filming of a soap commercial, and ends up the star of the ad. Soon after, Tony develops an itchy rash that turns out to have been caused by the soap. Angela must then decide if she wants to market a soap whose makers are not completely honest about its potential side effects.

Tony is greatly anticipating his dinner date with an old flame from Brooklyn, just as Angela is preparing for an intimate dinner for two at home. When Angela's guest cancels at the last minute, Tony reluctantly stays in Connecticut to keep her company, while attempting to keep, but slightly postpone, his date.

Angela's old sorority sister, Trish, is in town for a reunion. When Trish comes on to Tony and asks him to be her date for the reunion, Angela tries to warn an oblivious Tony about Trish's tendency to manipulate men.

At the market, Tony picks up a woman who believes that he is the owner of Angela's house and Jaguar. Meanwhile, Angela accepts a date with a man who believes that she is Rosie, Angela's flighty secretary. Both advise the other that no good relationship can begin based on a lie, and soon both are forced to confront their deceived dates.

Angela becomes involved with a gentleman who is quite the sports fanatic. He becomes more interested in hanging out with Tony and talking sports than in spending time with Angela.

Tony is moonlighting to raise extra money, which Mona believes is to take care of a secret girlfriend in Brooklyn. Soon the truth comes out: Tony is still paying rent on his recently deceased father's apartment, so that he and Sam will have a place to go just in case things don't work out in Connecticut.

Forced to confront the fact that Samantha is not a little girl any more, Tony buys her her first bra. When it turns out not to be the kind she wanted, she asks if Angela can take her shopping. Tony is less than thrilled, however, when Samantha comes home looking a bit too grown up.

It's time to paint the Jaguar, and Angela wants the new color to be sandalwood. Tony overrides her decision and has it painted diablo red. When Angela discovers this, she is enraged and forbids him from future decision-making, proclaiming that he is just the maid. He then takes this declaration to the extreme by dressing, speaking, and behaving like a prim and proper butler.

During a company party at Angela's house, Tony throws out one of her vice-presidents for saying unprofessional things about her.

Mona has been evicted from her apartment and begins looking for a new home. She takes Tony's suggestion to convert the loft above Angela's garage into an apartment. Angela is not happy about the new arrangements.

Angela's ex-husband, Michael, visits so that they can sign the final divorce papers. Instead, they find themselves back together again. With Michael back in the house, there's no longer a need for Tony, who is given two weeks' notice by Michael.

While Tony and Samantha live it up at the lavish estate of Tony's new boss, a wealthy older woman, Michael and Angela enjoy their reunion. But the celebration is short-lived, as they are eventually reminded of the professional and personal differences that drove them apart the first time.

A local news reporter, Bobbi Barnes, wants to do a story on the daily life of Angela. But when a series of innocent mix-ups leads Tony and Angela to wake up in the same bed, Bobbi's camera crew is waiting in the hall to capture the scene. Bobbi thinks she has a juicy story for her show, but Mona has other ideas.

Samantha is looking forward to the upcoming school dance, but Tony spoils her evening by constantly taking pictures of her and her date, working at the dance as a chaperone, and getting caught kissing her teacher in front of the entire class.

Nick, Tony's father-in-law, visits. He cannot bring himself to tell everyone that he will soon be imprisoned, so he instead claims that he is dying, then milks the sympathy.

Stories of Tony's rebellious youth are rubbing off on Jonathan, particularly when Jonathan brings home a hubcap stolen from a police car. Angela then decrees that from now on, she is to be consulted on all decisions regarding her son. Not to be completely overruled, Tony decides to handle the situation in his own way.

Tony fears he can't afford the ski club Samantha wants to join with her friends, but he lets her sign up anyway. When his attempt to economize by cleaning Angela's chimney fails, he must go back on his word and tell Samantha she cannot join. Refusing to borrow the money from Angela, Tony soon sells one of his prized possessions to be able to pay for Samantha's ski trip.

The family forgets Angela’s birthday. She comes home from a rowdy celebration with friends, just as Tony returns home from a police-sponsored demonstration of the effects of alcohol on the mind. Although they both are in a woozy state, Tony decides to bake her a birthday cake. They have a playful flour fight in the kitchen and end up kissing.