I remember I once sent Asterion with Argos and never sent him to the valley again, but in the next metting with Argos I answered with "I'm a sadist" and automatically I went to ruthless route, even if I haven't sent Asterion to the valley. In speedrunner background I sent him by accident in the chapter 12, and I went to ruthless again, but this I haven't saved my progress. Fortunately I found all endings, so I started again. I don't want to feel the same experience.