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Hilary is a student at Jefferson Elementary who Shawn had a crush on. They first met when she asked for someone to show her the way to the principal's office, and Shawn was happy to oblige. After watching a school film on puberty, Shawn asked her out on a date.

They snuck into a movie theater, but spent the duration of the movie throwing snacks at people. There Hilary taught Shawn to hold a malt ball in his mouth before throwing it, so that it sticks in peoples' hair. "She's majorly twisted," Shawn later described her with envy. They went on a second date, but it went pretty bad and Shawn said it would be their last date.

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