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Doug meets a girl from Sugar Hill (the rich section of town) and has a date with her in an expensive/fancy restaurant. He wants to get a new shirt for the date, but strapped for cash. Malcolm tells Doug about how his grandma will buy a hat for church on Friday, wear it to church, and then return it for a refund. Doug decides to do the same for a new shirt from a really expensive store using his father's credit card that was only meant for emergencies. A subplot in this episode is that Doug is warned that he is only being used by this girl as her "project" from the hood and that she doesn't have a real interest in him as a person. On the date, he realizes the warnings were right and also gets the shirt he intended to return for a refund messed up. He is able to get a replacement shirt from a street vendor, but has to come clean to his dad about the credit card charge.