I'm actually looking into the Dare #2 bugs today.
But to address the time limit question, there is a time limit of a week on it, but what happens (or what is SUPPOSED to happen) is Callie either admits she didn't complete it and pays the penalty, or asks for another week to do it and generally the request is granted.
With the exception of the first dare, which is a membership test, it all comes down to meeting attendance as to whether or not the dare gets turned in as successful or failed, given that sometimes Callie can wind up getting grounded when she's caught sneaking back in after doing it.
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