After so many attempts and failures, Sacchan and Kondo try to play matchmaker to get the other's love for them to win a bet.
A monologue by Sarutobi reveals that not only she can no longer wait for reuniting with Gintoki. To remedy her situation, she dresses up as a large slice strawberry shortcake at a cake store. She does this in the hope that Gintoki chooses to use his free cake coupon on her. As Gintoki peruses the available cakes, Sarutobi snaps and offers herself to him. He, however, completely ignores her and immediately when she leaps in front of him, Gintoki kicks her out of the store. Feeling dejected after being rejected once again by Gintoki, Sarutobi lets out a deep sigh and notices Kondo at that very moment do the same.
The two then talk about why they technically weren't "sighing" about something. It then escalates quickly about how the two have awful luck snatching those of whom they stalk. Kondo then proposes that they help one another with their love problems. Sarutobi accepts and claims the one who wins will be proven to be the happiest. Eventually, Sarutobi meets with Shinpachi and Otae. She reveals to them that Kondo has found another woman he's in love with and presents them with a coded love letter as proof. Further proof that Sarutobi shows is a spiked collar gifted to her by Kondo which is great because she's half gorilla. With this revelation, Sarutobi is convinced she's won. Meanwhile, Kondo stalks Gintoki who easily becomes annoyed by it. On the topic of stalkers, Kondo mentions that Sarutobi has decided to stop stalking Gintoki on the account of finding her true love. Gintoki shows disinterest in the news, however, Kondo is confident he's won.
Afterward, the two reconvene at a dango shop to elaborate on each other's progress. After hearing the other's progress the two disparage each other, but decide to join forces for an infallible direct plan. The two then dress up as a chained up masochistic couple, much to Kondo's chagrin. When the two inform Gintoki and Otae about their engagement, they take it in stride, which disappoints Kondo and Sarutobi. Lamenting over their failures, Kondo and Sarutobi respectively reveal to Gintoki and Otae that their relationships were fake. They also allude to them who they truly love. So taking matters into their own hands Gintoki and Otae respectively confront Sarutobi and Kondo with who they truly love. ...Or so it's thought.
- Sakata Gintoki
- Sarutobi Ayame
- Kondou Isao
- Shimura Tae
- Shimura Shinpachi
- Hasegawa Taizou (cameo)
- Catherine (cameo)
Gintoki meets Santa and Ben (his reindeer) as they reunite.
It's Christmas time and Gintoki meets up with Santa again who's promoting a cabaret bar. Immediately, a debt collector starts to hassle with Santa demands that he pays back his debts. This continues until Ben (his reindeer) arrives and pays off Santa's debt. Gintoki then meets with the two calling it a fateful reunion. In celebration for their reunion, they eat at the Oden shack where they originally ate at when they first meet. A lot has changed between Santa and Ben since Gintoki last saw them. Santa quit his job and has become a tout, while Ben now runs a large money lending business. Although Ben has gotten the longer end of the stick, he feels that his soul is empty.
Hoping to rekindle each other's soul with a scintillating experience, Gintoki procures a sleigh for them to use. The same exact one used the first time they met that also still has Musashi on it as well. After Gintoki tries to coax Santa and Ben to use it, a pregnant mother goes into labor as her daughter cries for help. The mother is the same one who retaliated against the group for trying to give her daughter Yuri a Kendama. With no time to lose, the group transports the mother to the Oedo hospital where she safely delivers the baby. Before Santa is able to leave, Yuri thanks Santa for what he's done.
Afterward, Gintoki and Kagura enjoy watching the Christmas special on the TV together, while Santa's bells could be heard ringing.