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.
Tony is hesitant to go public with his and Angela's new relationship, so the two must lie and sneak around in order to spend time together. An accident by the lake forces them to reveal their secret.
Tony's love for Angela becomes obsessive infatuation, and it begins to drive Angela crazy.
Sam dates Pierce, a stockbroker, who acquires Tony as a client. Tony becomes infatuated with his own financial fate and demands much of Pierce's time, which takes away from Pierce's time with Sam.
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 him 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 is thwarted by a series of accidents that consistently plague her. The joy of the proposal is short-lived when Angela turns him down.
Tony does not understand Angela’s rejection and he becomes a blithering idiot. Meanwhile, she continues to question the sincerity of Tony's intentions. Mona and Sam help her see the real root of the problem.
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.
A former owner of Angela's house visits and offers her a sizable amount for it. Tony and Angela begin house hunting and find what they think will be their perfect home.
Financial hardships at the Bower Agency have Tony and the family cutting costs. The cutbacks are especially tough on Angela. When Tony learns of her impulsive shopping spree, he forces her to surrender all her credit cards.
Al is having difficulty getting his own apartment because the landlords would all rather rent 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.
Tony feels pressured to accompany Angela to all her social events. This full schedule has him feeling like he has no time to himself anymore. He fakes a headache resulting from a head injury to get out of going to the ballet. While resting, he gets an unexpected visit from his Brooklyn friends, who quickly organize a poker game -- which Angela walks in on.
Tony dreams what his life would be like if he had continued to play baseball with the Cardinals. He learns that fame and fortune without Angela would not make him happy.
Repeated instances of swollen 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 and between Tony and Angela.
Frequent fighting between Tony and Angela lead her to take a vacation to a resort, accompanied by Sam and Mona. While there, they meet a man who bears a striking resemblance to Tony. Angela soon realizes that not even a look-alike can take the place of Tony.
When a leak in the roof is discovered, Hank's father and his team attempt to repair it. Tony's persistent meddling in his work leads him to quit the job. Tony then hires Hank and Jonathan to help him finish the job.
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.
Angela attempts to adjust to her new life in Iowa, but discovers that she really wants to be back east, working at her agency. The conflict of professional interest threatens to split up Tony and Angela. Their relationship comes full circle with Tony again knocking on Angela’s front door.