The Winner - Season 1 Episode 1 Pilot
Overview: In the summer of 1994, a thirty-two year old named Glen Abbott was still living at home. Alison McKellar, the only girl that he ever kissed, returns to town with her son Josh. The return of Alison gets Glen thinking that it's time to grown up and win her love. Josh and Glen become friends, and end up double dating with Alison and Josh's dream girl.