Tora-san befriends the descendant of a feudal lord. The man asks Tora to locate his deceased son's wife who resides somewhere in Tokyo.
When Tora-san's infatuation with his nephew's school teacher causes family turmoil, he leaves on his travels again. When he returns, he falls in love with the teacher's mother.
Tora-san becomes friends with Toraya's newest tenant, a pachinko-playing electrician that goes by the nickname Watt. Tora attempts to match Watt with a young waitress.
Tora-san's nephew Mitsuo is exchanging letters with Izumi, a former classmate whose parents divorced and took her out of Tokyo.
Tora-san leaves Shibamata once again after an argument with his family and finds himself at an inn where he meets Tomekichi, a young man who looks up to Tora-san.
After a chance encounter with Hiroshi's father on a bus, Tora decides to get serious and reflect on the mortality of man. His plans are derailed when a beautiful lady starts working at Toraya.
Tora befriends a pretty barbershop owner and runs into Izumi. When Tora twists his ankle, Mitsuo comes to care for him and see Izumi. Meanwhile, Izumi must choose between her new job in Tokyo and returning to Nagoya to care for her mother.
When cabaret singer Lily writes Toraya about her illness, Tora-san rushes to Okinawa to be by her side.
When Izumi can't stand seeing her mother flirt with other men, she leaves home. She sends a letter to Mitsuo and Mitsuo goes looking for her. But Izumi unexpectedly meets Tora-san.
Tora-san, an itinerant peddler who is thrown out of his father's house twenty years before but reconnects with his aunt, uncle and sister Sakura. Tora wreaks some havoc in their lives, like getting drunk and silly at a marriage meeting and ruining Sakura's chance to marry someone, as well as just being a real pain to those around him. There is a sentimental side to him also, and the best way to describe him is that he grows on you.
Tora-San returns to Shibamata just before his family leaves on a trip for Kyushu. Later, he encounters an old school chum and begins to have feeling for his artist sister.
Kuruma Torajiro is discovered looking around Kyoto for someone special to him.
Traveling salesman Kuruma Torajirō falls in love with an inn manager as New Year's approaches.
Tora-san visits Hokkaido and is reunited with Lily. Now divorced, she plans to resume her singing career and renews her unusual relationship with Tora-san.
Tora-san arrives in Shibamata on Mitsuo's first day of school only to find that on his account, Mitsuo was embarrassed. After a fight with his family, he goes to a bar to drink, then brings home a surly old man with a sad story, whose identity will surprise everyone. Later, Tora meets Botan, a geisha.
After winning big at the races, Torajiro Kuruma wants to take his aunt and uncle on a trip to Hawaii to partly pay the great filial debt he feels he owes them, but the plan hits a snag. Also, a pretty kindergarten teacher rents a room at Toraya.
Tora-san returns to his family home to learn that his brother-in-law cannot go to Mitsuo's (Tora-san's nephew) athletic event. Tora-san volunteers to take his place, but gets into an argument with his brother-in-law's boss and returns to the road. He meets a young woman in Niigata who, unbeknownst to him, is a popular enka singer.
In Shibamata, Tokyo, Tora-san's family prepares for a wedding. Meanwhile, the traveling Tora-san meets an old acqaintance in Iwate Province. Tora-san refuses to drink with him, afraid that the acquaintance, now settled and married, will again become attracted to Tora-san's wandering existence. Tora-san becomes attracted to a female barber, but must break off their relationship so that she too can live a secure life. She instead gets into an abusive relationship with a motorcyclist.
In Nagasaki, Tora-san and an acquaintance help an old woman who has fallen and injured herself. She invites them to her home where the three share a night of eating and drinking. The old woman's health deteriorates and she dies. At her funeral, Tora-san falls in love with the old woman's daughter, but winds up acting as a go-between for her and a young law student.
Tora-san's family's neighbor, Akemi, who had been married in Marriage Counselor Tora-san (1984), runs away from her husband, who is only interested in work. Tora-san follows her to Shikinejima, and attempts to bring her back to her home. In doing so he encounters a school-reunion group who are traveling to meet their elementary school teacher, which is a reference to the film Twenty-Four Eyes by Keisuke Kinoshita. Tora-san joins them and falls in love with the teacher.