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Everyone loves an underdog!
At first I didn't think I was going to like Carrie...but as the story goes on, the wimpy-ness becomes kind of endearing...he just wants to please everyone and avoid confrontation, and we all know people like that. The fact that he FINALLY grows some BALLS and says what he really wants to at the absolutely most inappropriate time is great comedic timing. And, as everyone loves an underdog, of COURSE you want him to fight and win - not only the money, but the pride & confidence in himself he probably never would have had otherwise.
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