Josie develops a crush on her English teacher, Sam Coulson (Michael Vartan), and becomes the top student in his class. After reciting a romantic excerpt from Shakespeare to Sam, Josie has horrible flashbacks to when she read a romantic poem aloud in class to her high school crush, a popular boy named Billy Prince (Denny Kirkwood), who later asked her to their senior prom, making her dream come true. However, on the night of the prom, Billy arrives with another girl and both of them hurl eggs and insults at Josie, humiliating her and breaking her heart.