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 befriends the descendant of a feudal lord. The man asks Tora to locate his deceased son's wife who resides somewhere in Tokyo.
Tora-san is inspired to pursue an education after a visit to the grave of a woman he met years ago. When he returns to Shibamata with the intent to study, he falls for Toraya's new tenant instead.
Carrying a bag full of samples, Mitsuo makes rounds to shoe stores in remote cities. While staying at budget hotels, his thoughts turn to Tora-san.
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 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.
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.
When cabaret singer Lily writes Toraya about her illness, Tora-san rushes to Okinawa to be by her side.
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.
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.
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 helps out a runaway bride.
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.
After a friend and business colleague dies, Tora-san visits the man's daughter, then takes her to Tokyo so she can study for a night school exam.
When his travels bring him to Osaka, Tora-san falls in love with a local geisha. He helps her to track down her estranged brother, and informs his family that he plans to marry her. His plans are foiled when the geisha informs Tora-san that she is engaged.
Tora-san returns to his family's home to attend an elementary school class reunion. After he embarrasses himself by getting drunk and insulting all his ex-classmates, he resumes his travels. In Kyushu he meets an outspoken 18-year-old girl who becomes enamored of Tora-san and follows him around. One of Tora-san's old friends is terminally ill and makes Tora-san promise him to marry his wife once he is gone.
Tora-san gets into an argument with his uncle and sets out on the road again. In Kyushu he meets a young woman named Keiko and the shy zoologist Saburō, and attempts to play matchmaker between the two when they all return to Tokyo.
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.
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.