okay so here was the problem i found, when i would return to fight the boss in the second dungeon after already losing, when i try to fight the second time i'm unable to interact with or fight her and i'm basically stuck unless i restart from past save and fight her from the beginning all over again.
rickurai
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the thing is that is what I actually did. I left the demoness relationship and focused on the story and other characters relationship. now I have completed events for every characters as well as every mission and only demoness relationship is left for me which is not moving forward for some reason. just for extra information to let you know my situation I have done all 95 events, 95 out of 99 secret events are done out of every character event that I can see only the demoness is left to complete.
so I'm at level 4.9 with the demoness and unable to continue to the relationship going forward. i have completed almost every mission as even the bartender isn't giving any hints anymore. the fortune teller keeps telling me to lets her win but it doesn't seem to be doing anything. how do i continue leveling up the relationship with her?