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Under Kaishu, Ryoma learned the art of Not Being a Retard, and with his newly acquired brains, got put to work organizing trade fleets which, to the surprise of everyone including Ryoma himself, he was apparently very, very good at, and he liked it very much. The rice buyout he manages to organize during the Honnoji FINAL campaign is a reference to all this.

Around this time, he was staying over at an inn, where he started making sweet passes at a girl working there called Narasaki Ryo, better known as Oryo. Oryo’s mom was apparently easily tricked by swindlers (or a gambler), and one day someone burst into the inn to tell Oryo that someone had just swindled her mom into selling her two younger sisters, one to a brothel and another to a geisha house. According to Ryoma (this story being straight from his letters), Oryo immediately grabbed a dagger, walked out of the inn, and traveled to the brothel, with Ryoma following her. When she reached the brothel, she applied the gentle diplomatic art of kicking the door down and threatening to stab motherfuckers until they gave her sister back, picking a fight with a tattooed armed guard and howling at him that she’d stab his guts out if needed if he didn’t stand aside. There was apparently a shouting match between them that mostly consisted of “FUCK YOU I’ll KILL YOU / NO, I’LL KILL YOU” and eventually scared everyone to the point they figured it was worth giving the kid back rather than facing a possible double murder.

Ryoma, who thought this was the coolest thing he’d seen in his life, later helped her recover her other sister and asked her to marry him, bragging in his letters to his sister that he thought she was even tougher than him.

He would then go on to arrange his most famous stunt, the negotiation between Satsuma and Choushu, that would lead to the successful overthrow of the Shogunate.