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what could I do to determine if you top or bottom?  I want to avoid doing an explicit dialouge box to select. 

I had the idea of maybe the time you spend topping vs bottoming the minor characters, like if you spend more time with the tanooki and slime you get bottom and dragon and kobald you get top, could be a 50/50 if the times are really close

(+2)

I think a super simple implementation would just be holding down while standing near the character rather than up.  Up to top, down to bottom.  :)

(+1)

That works actually.