Being so many loops in, we're missing a bunch; unless he also had the whole "world from a game" and system messages, he should have acted differently during the initial loops, as they together learned how restrictive the game is to following the plot (Rather than infinitely living identical lives over and over, they would reasonably choose to do different activities in other loops, etc).
We got some slight hints to the system reseting if things go to awry, as it seems like it was still relatively early in the other mans route when the memory erasure happened, yet everything was reset, so either it was a corrective action, or he's aware enough of the plot to know where "bad ends" occur and force them out.