On the road again, Torajiro meets a kindred spirit in Lily, a lounge singer.

When cabaret singer Lily writes Toraya about her illness, Tora-san rushes to Okinawa to be by her side.

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 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 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 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 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.

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.

After Hiroshi is injured in a workplace accident, Torajiro gives Sakura the money he has saved and leaves to work as a traveling salesman once again. During his travels, Torajiro meets a father who shares a drink with him. In the morning, Torajiro is shocked to learn that the man has left his baby behind and a note asking Tora to take care of the child.