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.
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.
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.
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 potentially harmful side effects
Tony is greatly anticipating his dinner date with a girl in Brooklyn, just as Angela is preparing for a business dinner for two with a client. 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.
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.
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 brassiere. When it turns out not to be the kind she wanted, Tony enlists Angela's help in buying Samantha new clothes. He is less than thrilled, however, when Samantha comes home looking a bit too grown up. (Note: This episode was originally titled "Samantha's First Bra" but was later changed due to censoring problems.)
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.
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.
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 himself 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 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.
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.
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.
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.
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.
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.
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.
Sam has had a big argument with Bonnie. Tony wants to see them both together again but Sam only agrees if he for his part makes it up with his old foe from high school, Mickey. Therefore Tony invites Mickey who has in the meantime become a Father. But when Tony annoys him too much Mickey strikes a blow.
As Tony doesn't want to sell his only 'Tony Micelli Baseball card', he tells Mr. Ferguson he has none. Angela, who has listened, now wants to get one for Tony. The trader Angela has asked calls Tony shortly after and offers him a lot of money which he really could need to buy Angela a christmas present.
Due to heavy snowfall life in Fairfield is down. To pass the time stories are told. Topic: Who has brought together the two families - Sam, cause she's the reason Tony wanted to move; Tony, cause he wanted to make life better for Sam; Jonathan, cause he needed someone who takes care of him; Angela, who needed someone for the household;or Mona, who has 'found' Tony ?
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.
Samantha thinks her boyfriend Chad is the cat's meow when he writes a song just for her. Word gets around, and the tune is heard by legend Ray Charles whom Angela cooerses into recording it for her ad agency. When rat Chad starts seeing another girl, Samantha is so infuriated she demands the recording not take place. It takes a stellar performance of the song by Ray to make Samantha see that her friendship with Angela is more important than getting back at Chad.
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'.
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.
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.
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.
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.
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.
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.
In an effort to better himself, Tony heads off to college. The public speaking class is headed up by a strict grammer enthusiast who singles Tony out as an impossible case. Its My Fair Lady as Tony does a complete turnaround, but he alienates himself from his family and friends and must rely on the "inner Tony" to figure out who he really wants to be.
Mona has saved the order for Angela and designs now the new get-up for the magazine 'Mature Woman'. Jonathan runs for treasurer in his school. For the magazine's cover Mona let herself photograph scantily dressed. When Jonathan schoolfellows see this cover, his chances getting elected seem to be gone.
Again Sam comes home with an expensive T-shirt. This time Tony wants to show her that she can have them cheaper and produces some of them himself. Angela and Sam persuade him selling them at the flea market. Both of them help him, especially Sam hopes she can get rid of her debts which she has made at Jonathan. But it happens what has to happen: Angela and Tony quarrel.
Discouraged that Angela had to pay for an escort for a dinner event, Mona convinces Tony to ask her out on a date. The date hardly seems like a first for them, though, as they discover how much they know about each other. Things get ugly when Angela learns the reason behind the evening, and attacks an obnoxious comedian.
At a practical program, where students are assigned different jobs, for Sam and Bonnie there are only two left: domestic engineer with Tony or advertising with Angela. Sam decides in favor of the housekeeping job which she regrets soon. The following day Bonnie and Sam switch their jobs but working for Angela isn't any fun, neither.
Sam's friend Scott gets nervous about French finals, so on test day, Sam gives Scott the answers. When Tony finds out, he takes Sam's car privileges. But when Sam has to take chemistry finals, someone gives Sam the answers to the test, but she does not use it. When the teacher sees the answers under Sam's desk, he calls Tony. But will anyone believe anything she says?
Charlie, Sam's female friend from Brooklyn, visits while Angela is preparing for a dog food commercial. Charlie talks Sam into ditching school for the day and going to the beach, but Tony catches them before they leave the house. When Tony calls Charlie's mother to tell her, he learns that her mother doesn't care about Charlie and doesn't want her in her life.
Angela brings the family to a psychiatrist for counseling when she thinks Sam and Jonathan's fighting is getting to be too much. The psychiatrist reassures the family that their family is emotionally healthy. But his evaluation of Tony's busy life prompts him to ask Tony to continue counseling with a group of parents who risk burning out.
To fill out his semester class schedule, Tony takes an independent study course, expecting it to be an easy A, and that he won't have to do any work. The course puts him in a third-grade class, where the teacher orders him to assist her on the first day. After an initial struggle, he finds he is able to work well with the students, and is soon considering becoming a teacher.
Some bad experiences at school, including being assigned to play the accordion, have Jonathan's self-esteem at rock bottom. Tony helps him overcome his depression by introducing him to an old friend of his, who is now an accordion player. Jonathan soon enjoys playing the accordion, but when Tony encourages him not to restrict himself to one activity, Jonathan misinterprets Tony's intentions as disapproval for the accordion, and bans Tony from his first recital.
Sam and her boyfriend Eric want to attend a concert. But Eric usually spends the evenings with his (widowed) grandfather. So Tony gets an idea: Mona should instead spend the evening with him. But then when it turns out that Eric's grandfather is the man, who Mona let down 40 years ago at the wedding, the general feeling is at zero level.
Sam has spent the summer working at a ranch in New Mexico. When she calls home and announces that she'd like to move there permanently, Tony and the family fly out to change her mind. Tony is adamant that she return to Connecticut and go to college, but even more so when she meets her new boyfriend.
Because Sam has not the peace necessary to learn she wants to move into an apartment. She moves in with Beth who's living together with her fiance and is urgently searching for another lodger. After a big argument with Ben, Beth moves out. But Sam living together alone with a man isn't a pleasant thought, neither for Tony nor for her friend Matt.
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.
Hard times have begun in the advertising industry - and Angela isn't spared either. Tony takes over the financial management because he has economy experiences. He pinches and scrapes wherever he can.When Angela, totally frustrated, goes shopping, she runs into serious troubles with Tony. He without hesitation takes away all her credit cards.
Sam and her boyfriend Hank are planning to get married, and Sam must find the right moment and way to tell Tony. But a series of incidents, including Hank's plan of career change, a roofing accident, and an unexpected visit from Hank's parents, yield a chaotic scene. During the bickering that ensues, Sam and Hank sneak off to elope.
The house has a hole in the roof. This in conclusion leads to a rebuilding of Angela's bedroom. Joe, trained workman, carries out the job. But Tony, like it's his way, doesn't leave the workmen,like the others before them, in peace. This leads to a big argument between Joe and Tony - and Tony fires him and does the work now by himself. His team: Hank, Jonathan and Al.
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.