As a Homecoming Queen, Jen is asked to help Miss Freckling, who is the oldest living ex-Homecoming Queen, organize the special annual party for the all the ex-Homecoming Queens. At first, Miss Freckling acts very bossy, and Jen feels like not doing it at all, but then Henry, who happens to be Miss Freckling's neighbor and only true friend, shames Jen into helping the poor old woman, who doesn't have much in her life, except for that very special event. So Jen agrees to help with entertainment, and also names Henry her date for the party. However, she does everything her own way, inviting a drag queen quartet and choosing not-so-classical music. But Miss Freckling, albeit shocked at first, still enjoys the event after all. She tells Jen to be nice to Henry. Later, Henry tries to kiss Jen and tells her he's in love with her. However, Jen rejects him, citing the age difference and the fact that, at the moment, she isn't ready for any romance at all. Henry feels really hurt.
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