Without reading ahead and spoiling anything, here's a couple of thoughts:
① His “do I really need to hide the fact that I am looping?” is a very good question if the loop would reset his answer every time. But, first of all, his “save point” moves up in time (and thus might make his confession permanent); on the other hand, her saying “I just want to help you” would imply some potentially horrible method of breaking the loop.
② At this point the types of his death look so random that I am inclined to think of that as of a hint that either his destined person somehow changes over time (might be the result of his own actions in the loop) or that he is now destined to have a harem (that'd be a fun explanation).