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Achievements fall into three categories for me, General progress, like kissing and such, Specific events, like titty monster... then there are the story events. These are hard and I don't like giving hints for them. What I will say is that that one happens on Saturday Midnight and it requires the use of options that you are not expecting to use and that you will know immediately when you get it, if you're not sure, you haven't gotten it yet.