Psychologist Bob Hartley shepherds his "Fear of Flying" class on a graduation trip to from Chicago to New York. His wife Emily is supposed to jet along too, but Bob finds out why they honeymooned in Gary, Indiana - she's also terrified of airplanes. Bob schedules a confident, brilliant expert as guest speaker, his neighbor, airline navigator Howard Borden to comfort his class, which includes Mr. Carlin & Mrs. Bakerman.
Bob has no clue how to explain what a psychologist does, to a 3rd grade class. That's why his wife Emily refuses to invite him to her career day. Bob's strong ego can withstand such a blow, and his supportive friends, Howard & Jerry, though they are presenting at career day, wouldn't dream of ridiculing Bob about it.
Teacher Emily finds love with her hunky new tennis instructor, when Bob urges she get out of bed and enjoy her summer vacation. The instructor also slides onto Bob's couch as a patient, because Bob has no concept of the terrors of being incredibly good looking and constantly pursued by women with sudden desires to learn tennis.
Bob inadvertently takes a mismatch, boxing against his mom, over court-side seats at a Bulls-Lakers game. Dr. Bob Hartley is stung that his mother still calls him Sonny, and wishes he'd been a cartoonist instead of a having a private psychology practice, which she has no interest in. When Bob reveals to his wife Emily that he hasn't told his mother he loves her since he was a child, Emily persuades him to carpe diem over dinner, before it's too late, because floating like a butterfly has gotten him nowhere near getting Martha Hartley to treat him like an adult.
Bob's old girlfriend, Nancy, is in town with her husband, and asks Bob & Emily out for dinner. Emily is more curious than Bob. At dinner, Nancy tells Bob she is leaving her husband. Dinner is full of memories; lunch the next day is awkward.
Carol has a new boyfriend and their relationship interferes with her time at work. She thinks about moving in with him to be together more. Howard has another girlfriend and is worried about keeping her.
Bob makes plans with Jerry to watch Monday Night Football at Bob's place. Emily is upset because she feels left out. They argue the next night about his ignoring her. Since they do not go to bed angry, they stay up all night.
Being married now for three years, Bob and Emily, both feeling like their careers have taken precedent in their lives up to this point in their marriage, decide that perhaps it is time they started a family. This feeling grows stronger when they attend a dinner party in the building where all the other guests and the hosts are happy parents. As the party hostess, Margaret Hoover, is in the latter stages of her current pregnancy, Bob gets his first direct taste of the feeling associated with a yet unborn baby. Having learned earlier from Jerry that he was adopted, ...
Bob & Emily return from vacation. At the office, Bob finds out Jerry is engaged to someone he just met and plans a fast marriage. Everyone finds her pushy and controlling. Bob worries about Jerry making the right decision.
Bob feels like everyone wants his time and that he has no time to himself. He decides to stay at a hotel for a night for the solitude. Everyone thinks he is leaving Emily. Meanwhile, Emily tries to get a book for the school library.
Emily takes Howard to the dentist in the same building where Bob works. Howard has a high from sodium pentothal, meets Carol, and is utterly charming. Carol asks Emily to set them up on a date. The foursome go out; Howard is back to normal.
Jerry talks to Bob about not being happy in life, and then decides he wants to see Bob professionally. When Bob presents the bill to Jerry, he is shocked to see how much he is charged. The bill causes problems in their friendship.
Carol turns 29 and feels unfulfilled. She quits her job to explore other options. Carol joins one of Bob's group sessions and as the group explorer's Carol's feelings, Bob is asked how he feels. The group treats him as just another member.
Howard's sister Debbie, visits, and he wants to remove all signs of his dating habits. He thinks she is young and impressionable. Debbie arrives and Emily sets her up on a date. Howard turns over protective.
Emily & Bob look at a house for sale and sign a contract. After they worry about what the change will mean for them if their contract is accepted. Luckily for them, the contract is not accepted and they are happy.
Bob's therapy group had a great session and Bob is reluctant to take a vacation during this time. Bob & Emily have a 63-day cruise scheduled and he thinks it is too long to be away. His patients encourage him to go.