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.
In late 90s Osaka, three people from various walks of life meet by chance. They team up to orchestrate a complex financial con targeting crooked businessmen in an attempt to solve their respective financial woes.
Torajiro becomes homesick during his travels after watching a television report about his hometown and meeting a young woman that reminds him of his sister Sakura.
After Torajiro's latest attempt to find a bride goes awry, he starts traveling again and runs into Utako (last seen in Tora-san's Dear Old Home), now a widow.
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.
Franz Bielek is a bailiff by conviction. However, his overzealousness is increasingly a thorn in the side of his superiors, so they transfer him from the provinces to Munich without further ado.