I just tried that. Got one date wrong and finished the game with all gems. Nothing unusual happened. Do I need to not collect them?
Edit: I've also completed it with one date wrong without collecting all gems. No difference.
YEAH SO IT IS IN A ORDER. basically idk if its like eh, but bassically i say first do nile and misty. and let em smash, then do sammy and poppi, like before give sammy the good answer first and then bad answer second. that way after u fuck up the robot you dont die, then just fail the ari and maddie date. sorry for the slight delay in my reply