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Junior goes to school dressed as a homeless guy for Halloween and, as luck would have it, the gorgeous and heretofore unattainable Penelope goes dressed as a homeless woman. Serendipity-doo!
Junior compliments Penelope's costume, saying that it's cute. She says she's wearing it to make a political statement—to protest the treatment of the homeless in America. She's going to trick or treat for spare change and donate it to the homeless.
Junior says he's wearing his costume to protest the treatment of homeless Native Americans. He says he'll also trick or treat for spare change. Then they can make a donation together! (Awww.)
Penelope miraculously agrees.
Later that night, Junior is trick or treating for spare change, and is jumped by three guys wearing Frankenstein masks. They spit on him and kick him and take his money.
Junior wonders if Rowdy was one of the guys.
Junior tells Penelope about the attack the next day, and she is horrified. She says she'll put his name on her donation anyhow.
After that, Junior assumes he and Penelope will get closer, but of course, this doesn't really happen. Junior doesn't become popular over night.
Junior wishes he could ask Rowdy for advice about winning over Penelope, but already knows what he would probably say: "The first thing you have to do is change the way you look, the way you talk, and the way you walk. And then she'll think you're her fricking Prince Charming" (11.68).