The Winner (2007)

S1E1 Pilot

During the summer of 1994, thirty-two-year-old Glen Abbott finds himself still living at home. When Alison McKellar, the first girl he ever kissed, comes back to town with her son Josh, it sparks something in Glen. He realizes it might finally be time to mature and pursue her affection. As Glen and Josh form a bond, they decide to go on double dates with Alison and Josh's ideal girl, leading Glen to navigate his feelings and take a chance on love.