Is there a way to be officially dating special characters like The Cheer Captain, professors, and the River Rat owner? I have the bars pretty much maxed out so I'm wondering if its a story event thing I'm waiting on
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Right now, no, a good chunk of special characters are locked out from being dateable. Some characters (like the Classroom Harrasser or the Roommate) become dateable after you finish their storylines, but others just can't be dated right now. The Cheer Captain, all professors, and the River Rat's owner all can't be dated right now