Jennifer Hamilton was one of Jon's classmates in high school.
Jon has said that he worshipped Jennifer in high school, though she thought he was a nerd. Years later, Jon came to a high school reunion in an attempt to impress her. When she started walking to him, he was unable to control his infatuation for her. Later, Jon tried to tell her how much he had changed since high school, only to be interrupted by Wheezer, who reminded him of when he blew his nose on the school flag.
Jennifer Hamilton has long red hair with violet lips. (Alternatively, blonde hair and red lips)
She wears a pearl necklace, heels and a turquoise or pink strapless dress to the reunion, which reveals her hour glass figure that Jon immediately finds attractive.