Otae requests the Yorozuya to do something about Kondou, who's been stalking her ever since she turned down his marriage proposal.
The Shinsengumi, the special force of the police that deal with terrorists, are conducting a raid while being followed by reporters in a show called Close up! 24 Hours with the Shinsengumi Elite Police! Sougo and Hijikata easily defeat the suspects they come across with. They wonder where their chief, Kondo Isao, is and expect that he is doing something respectable such as talking to a government official or cleaning his sword. In reality, he is at Snack Smile, a hostess bar where Otae works. He complains that he can't get a girlfriend because his butt hair is too thick but Otae tells him she would love her boyfriend even with a butt afro. Kondo realizes that he loves Otae and proposes to her. At the dojo, Otae tells Shinpachi that she rejected Kondo's offer. Kondo then purposes again by climbing a pole but Otae throws an ashtray at his face. Meanwhile the Shinsengumi special show continues. They once again wonder where Kondo is but Hijikata reassures them by saying he's probably training alone. Kondo is again seen stalking Otae on many occasions. The Shinsengumi special continues as Hijikata and Sougo try, but fail, to conduct traffic. At a restaurant, Shinpachi and Otae tell Gin and Kagura of Kondo's stalking. Gin gets angry because he is now introduced and plays the Gintama theme song. Shinpachi convinces Gin to help and Gin calls out Kondo who is hiding under a table. Kondo asks Gin his relationship with Otae and Otae tells him they are egaged. Kondo challenges Gin to a duel with Otae as the grand prize. At the showdown, Gin delays to show up with the excuse of having to use the toilet. The Shinsegumi special continues when a drunk causes a ruckus and ends up vomiting on Hijikata's pants. Back at the showdown, it is late and a crowd forms as Gin finally shows up. After they insult each other for a bit, Gin wages his life instead of Otae's so even if Kondo wins he wouldn't get her. Instead, if he wins Kondo will be free to "court" her. Otae tries to stop Gin from doing it. Kondo acknowledges Gin for this and drops his metal sword. Gin gives him his favourite wooden sword, a souvenir from Lake Toya, and instead Gin uses Shinpachi's wooden sword. The duel starts but the Late Toya sword breaks and Gin easily wins. Gin had cut the sword beforehand and tells Kondo the best way to settle serious matters like this is to talk. Shinpachi and Kagura beat up Gin because of his lack of samurai spirit. Otae says she is starting to understand Gin and walks away. Hijikata, followed by the camera crew, asks the crowd what was going on. He makes fun of the idea of the duel but is shocked to see Chief Kondo unconscious.
First 3rd year, class Z, Ginpachi-sensei!
- Sakata Gintoki
- Shimura Shinpachi
- Kondou Isao
- Hijikata Toushirou
- Okita Sougo
- Yamazaki Sagaru
- Harada Unosuke
- Shimura Tae
- The Opening in this episode played 10 minutes after the episode actually started, when Gin first appears.