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how to progress roomates GF storyline. stuck where she just says shes going to give challanges

also how do you get that to trigger cause i read somewhere you have to do a dare or something like that 

I'm already  in like the 3rd month. Does it take that long?

does anyone know how to get the roomates GF events to trigger?

so is he gonna update the game? should have just kept working on the other one