Lost In My Own World

Chad Stuart is a typical jock. Going to party's and dating girl is his daily routine. It may sound exciting but to him it boring. One day he attend a party, seeing his childhood friend Jess.
Jess was the complete opposite of him a social outcast, a cold introvert and a person with a bad attitude.
Between them a simple bet ensue.
Find her a boyfriend within 1 mouth and she won't rat on him.
Can he win this bet? or maybe being something more then childhood friend?