《男人之苦》50周年紀念作品，家族成員原班人馬上陣！

寅次郎的妹妹阿櫻 (倍賞千惠子飾) 在寅屋為滿男 (吉岡秀隆 飾) 去世6年的妻子辦紀念禮。滿男其後重遊舊地，發現從前傳統糖果店已變成現代咖啡廳，但屋內仍保持舊貌。

滿男如今已是個業餘作家，新作很受歡迎，在他新書的簽名會上，重遇了那個他曾答應結婚的初戀情人 泉 (後藤久美子 飾)。泉現居住在歐洲，因工幹回來日本。二人到了一間爵士樂咖啡廳聚舊，原來那兒的老板就是莉莉 (淺丘琉璃子 飾) — 寅次郎20年前在奄美大島戀上的情人，也是他一生中最愛。多年後重聚，三人回憶起寅次郎往日生活點滴...

On the sixth anniversary of the death of Mitsuo Suwa’s wife, a memorial service is held at Kurumaya, formerly a long-standing traditional confectionery store on the approach to Taishakuten Temple in Shibamata. It has been reborn as a modern cafe, but the living quarters in the back remain unchanged.

After the service, conversation inevitably turns to lively reminiscences of the past, especially the many times that Torajiro, a traveling salesman and the black sheep of the Kuruma family, brought his latest unrequited love interest back with him, sending the house into an uproar... Half a century has now passed since Torajiro, fondly (and not-so-fondly) referred to as Tora, first returned to Kurumaya after leaving home in his youth.

Mitsuo, who was an office worker for many years, now enjoys a career as a full-time writer, after a novel he wrote in his spare time won recognition. His latest work has also been well received, and a book-signing session is held for him to meet and greet fans. However, upon glancing at the waiting line, he is stunned to see his first love, Izumi Oikawa, who he had once promised to marry. She now lives in Europe but has returned to Japan on a business trip, during which she stumbled across Mitsuo’s signing event. He makes quick work of the session, telling Izumi he wants her to meet someone, then takes her to a small jazz cafe. Izumi takes one look at the proprietor’s face, and is astonished: it is Lily, the greatest love of Tora’s life, who she met on the island of Amami Oshima over 20 years ago. Reunited after so many years, the three share their dearest memories of Tora.

As they talk, Mitsuo and Izumi sense a warmth growing between them.

Later that night, Izumi visits Kurumaya...