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.
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.
After Tony and Angela have confessed their love for each other,they both now want to spend an enchanting evening together.But that isn't that simply,especially since no one can know about it.
Tony, like it's always his way, overdoes his relationship with Angela. But Angela doesn't dare to tell - and tries to get out of his way.
After a car crash Sam and Pierce come closer. When Tony finds this out after weeks, he - against the other's expectation - takes a fancy to Pierce and confides his money to the stockbroker. But like always he overdoes here, too, and he spends more time with Pierce than Sam does.
While Angela is away on business, Mona begins dating one of her biggest clients. She finds him thoroughly uninteresting and promptly dumps him. In an attempt to prevent from withdrawing his account from the agency, Tony accompanies him on a duck hunt. An accidental gunshot only makes things worse.
Tony feels inferior to Angela's success. A letter that addresses him as "Mr. Angela Bower" doesn't help his self-esteem. He takes a second job at a bar, but that proves to be a mistake.
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.
Tony is angry at Angela for her rejection. Meanwhile, she continues to question the sincerity of Tony's intentions.
Mona's mother visits and gives the subtle impression that she doesn't want Tony and Angela to get married. Mona can't convince them that her mother is manipulating them, trying to turn them against each other.
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.
Angela gets a generous offer for her house. Tony persuades her to sell and move into a new one because the current house belongs to 'Angela & Michael' and not to 'Angela & Tony'.
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.
Al is having difficulty getting for his own apartment, because the landlords would all rather sell to a young couple than to a single guy. Sam agrees to pose as his wife, but Tony is upset when he discovers the charade, and insists Al stay at Angela's house. The family comes to regret this.
Angela books up the whole time with some events and visits. Tony has to fall back on excuses to be together with his friends. But Angela catches on to him.
While he is unconscious, Tony dreams how it would have been as a baseball star if his injury had not happened.
Repeated instances of swelled lips have Tony frantically searching for the cause of his affliction. Angela notes that each occurrence happens just after they mention their wedding, and she begins to worry that the swelling is a sign that he isn't ready for marriage.
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.
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.
Sam and Hank return from their honeymoon to learn that married couples aren't allowed to stay at the dorm. Tony skeptically agrees to let them stay at the house. Despite a sleepless first night for Tony, he and Hank soon bond. This creates tension between Sam and Hank.
Angela, accompanied by Mona, goes to a health resort to get some distance from Tony and his temper. There she meets Tom who, bylook, could be Tony's lost twin brother but his way is completely contrary to Tony's.
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.
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.