I wonder how long it took for Jacobi to start fearing Questions Only with Kepler. We know that he's stubborn and Does Not Like To Lose, so how many times did he start a game thinking that he could beat Kepler this time. I genuinely think that, at the beginning when Jacobi was feeling really competitive, a game could last At Least two days. Maybe longer. They would even keep it up during missions.
Once, Kepler got shot and he still said "Mister Jacobi, could you help me bandage this up?" He would not crack and Jacobi lost every. Single. Time. Maybe except for one time when he had resigned himself to losing forever that re-sparked that competitive spirit (did Kepler tactically allow Jacobi to win so he'd keep playing? Who knows). I just know that there has to be some deeply painful (read: hilarious) story behind Jacobi's punched-in-the-gut reaction when Kepler mentions Questions Only and his complete denial in even Entertaining the idea.












