Glen Abbott (Rob Corddry) is The Winner, an exceptionally wealthy entrepreneur, but it wasn’t always that way. In fact, up until the age of 32, Glen lived at home with his parents and had only ever kissed a single girl. When he was 14. Eighteen-years later, when that girl, Alison Miller (Erinn Hayes), returned to town, something happened that would drive Glen towards his future success. From the creator of Family Guy comes a twisted middle-aged 'wonder years' that speaks to the slacker in us all.