Continous actions punishment

I dont know if this is the right place to post this , But you all seem like a bunch of smart individuals, How would i go about setting up a punishment system for a character in the game for repeating the same actions 2 nights in a row (Example, There are 3 paths, the character goes down path one night one, and he gets through safe, but night 2 comes along and he goes along path one again and now a monster shows up. How would i go about that??