Am i missing something or are some of the stat checks impossible to do before u get the option to start lvling said stats. IE flirting with the princess when u first meet, Kindness check with liz, Charisma check with Naomi etc.
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That's true, some of the early stat check can only be passed with your starting attribute. Some also provide you with an option of losing points with the girls but increasing your stats (by learning not to do it again).
In the long run, failing stat check won't matter much. When there is an important stat check that you need to pass, it'll be included in the quest requirement.