They never tell you this but that second round for that scene only triggers if you take the pill DURING the third time you lose to chara taking it the previous 2 times just erases it from existence and you effectively wasted it that is all
Bruh, there should be a check for this until you get to a scene.
Well, would you like to know something? I did just that, took the pill on the 3rd loss and guess what? It didn't fucking trigger.
Weird cause it worked for me