The Winner Season 1

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.

Alison invites Glen over for dinner, at first, he is pretty excited until a co-worker of his tells him that she may want more than just dinner. Embarrassed by his lack of a sexual experience, he decides to visit a massage parlor to learn a few tricks before his date.

Glen's parents' marriage begins to come apart with Glen spending so much time with Alison, her son, and her boyfriend. When Glen realizes that he has overstayed his welcome, he decides to try and get his parents to rekindle their relationship.

Alison can't join Josh on his trip to Albany for the State Spelling Bee, so she asks Glen to chaperone. Seeing that no one there knows the two, they decide to reinvent themselves to attract the ladies. Glen becomes airline pilot "Lance Manley" by wearing a toupee, and Josh pretends to be a cocky champion speller.

Josh begins hanging out with a new friend at school. Jealous of Josh's new friendship, Glen decides to find himself a new friend too, who turns out to be a gay man with a crush on Glen.

Glen, posing as Josh's dad for a parent-teacher conference, reunites with his old homeroom teacher, Miss Burko. Glen ends up getting his own private lesson in love.