The Winner (2007) - 1x02 - The Single Dates

In the magical summer of 94, Snoop Dog was climbing the charts, Olympic skater Nancy Kerrigan was clubbed on the knee and 32-year-old Glen Abbott (Rob Corddry, The Daily Show) was still living with his parents when the only girl he ever kissed, Alison McKellar, returned to town with her 14-year-old son Josh. The recently divorced Alison inspires Glen to become a grown-up to win her heart. Glen and Josh become fast friends and end up on a double date with Alison and Josh's dream girl.

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