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.
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.Watch Now:Amazon
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.Watch Now:Amazon
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
During a company party at Angela's house, Tony throws out one of her vice-presidents for saying unprofessional things about her.
Mona meets Jason, the man of her dreams, but she's old enough to be his mother! After much hiding the truth comes out and Angela, who previously stated that age had no part in love, is aghast. It's not until Jason's parents tell Angela that Mona isn't good enough for their son that she stands up for her mother and does an about-face of her opinion.
For the weekend Angela goes to Maine with her friend Geoffrey. Tony now alone at home, the kids are on a school trip to Washington, invites his old flame Tanya. Angela and Geoffrey couldn't manage to go to Maine and return unexpected.
Jonathan, because he takes life too serious, should do something else than always studying. He decides in favor of gymnastics and Tony should teach him. During a competition he falls due to his overzealousness and breaks his shoulder. And this is something Angela really isn't happy about.
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.
Part of settling into his new home has Tony using Angela's personal bathroom and getting an eyeful when she steps out of the tub. Neither of the two stubborn housemates accept responsibility, and disagree to an extent that Tony's new girlfriend gives him the heave-ho. Mona's advice about role-playing to better understand each other's point of view helps Tony and Angela see that they aren't angry after all.
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.Watch Now:Amazon
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.
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.
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.Watch Now:Amazon
Sam wants to queue for cards for the Beastie Boys concert overnight.Tony allows it not without remarking he has done much wilder things in his youth. During the stories told by Tony and Mona, Angela realizes that she has missed a lot. Now she wants to catch up on some 'action'. So she makes up a list what to to: Among these is a meeting with Jake 'The Snake' and a trip to his 'Rock of Inspiration'.
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 gets invited to a dinner at which Frank Sinatra is to perform; Tony, a huge Sinatra fan, is to be her guest. When business affairs leave her unable to go, Mona goes in her place, but doesn't tell Tony that the ticket is nontransferable.
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.
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.Watch Now:Amazon
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.
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.Watch Now:Amazon
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.
On the spur of the moment, Tony accepts a date with a woman he meets at a bar. Having second thoughts, he cancels the date the next day, only to learn later that the woman is the professor of his new 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.
Young Samantha has reached a teenage milestone - she has her driver's license! But in upscale Connecticut she feels left out when Bonnie gets a brand new car but Tony buys Samantha a hazard light on wheels! It comes down to pride vs love when it's discovered she's parking blocks away from her school.
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