Jack finds his world turned upside down the minute he lays eyes on Kat. From then on, his life becomes a mess of the unexpected. When he finds out that Kat isn't exactly single, he plays the field in an attempt to make her jealous. He walks the city with Jennifer, a waitress, and parties with Mickey, a fun girl in his history class. These girls still can't keep him from wanting Kat. He almost has her within his clutches, but then something terrible...