The Winner: Glen Reunites with His First Crush in the Last Episode

This offbeat sitcom, The Winner, never caught on with a large audience and was cancelled after a six episode run. The last episode aired on May 16, 2007 and is entitled “Hot for Teacher.” Here’s what happened.

In an effort to impress an attractive classmate named Wendy (guest Kelli King), Josh (Keir Gilchrist) starts cracking jokes in his English class. Tired of his interruptions, Josh’s teacher Miss. Kelly (guest Katey Sagal) wants to have a meeting with one of his parents.

Later, Josh tells Glen (Rob Corddry) about this development just as his Mom, Alison (Erinn Hayes), comes home. She’s had a really long day at work and has had a fight with her boyfriend Gary. Glen’s delighted to hear about the latter.

Afraid to hit his Mom with more bad news, Josh asks Glen to pose as his father. Glen agrees, especially once he finds out that the teacher is attractive. Glen had a major crush on his own English teacher years ago.

Josh asks Glen if he has any clothes that would make him look like a dad. We next see Glen entering the classroom dressed and acting like Bill Cosby from The Cosby Show, complete with a loud sweater and a cigar.

During the course of the meeting, Glen realizes that Miss. Kelly is actually his former English teacher crush. She changed her name from Miss. Burko when she married and asks that he not call her Miss. Kelly. In his excitement, Glen comes clean that he’s not actually Josh’s father and she tells him that he can call her “Lydia.” She’s recently divorced because her husband fooled around with a woman Glen’s age. Miss. Burko begins to look at Glen in a new way and asks him over for dinner. He’s thrilled. She offers to give him directions but he tells her he already knows where she lives.

At dinner, Miss. Burko tells him that he’s wonderful company, despite his not having said a word. She then suggests that they watch TV which, of course, is in her bedroom. Once there, she starts to seduce him. Glen, of course, is clueless and says, “Miss. Burko, you’re trying to seduce me.” When he has a hard time unfastening her bra, Miss. Burko thinks that he wants to role-play — she’s a naughty schoolteacher and he’s a young virgin student. He concedes that it’s a role he can handle.

We next see the two in bed, having made love. He’s embarrassed at how quickly things happened and she says that she had no idea that he was actually a virgin. After thinking about it for a moment, Miss Burko becomes happy about the prospect of teaching Glen. He’s delighted about the idea of having sex again and earnestly asks her to grade his performance. She coyly tells him that, for now, she can only give him an “incomplete.”

The next morning, at breakfast with his parents, his Mom (Linda Hart) asks about his dinner with his former teacher. Glen is certifiably giddy and Irene realizes that he’s had sex. She’s horrified while his Dad (Lenny Clarke) is thrilled. Ron gives him a bottle of champagne that he’s been saving to celebrate the event.

We next see a montage of images of Miss Burko instructing Glen on how to become a better lover, both in the classroom and in the bedroom.

At the Reel World video store, Josh tells Glen that, because of Glen’s new relationship with his teacher, he’s free to entertain the class and his relationship with Wendy is amazing. Wendy and he have just talked for 45 minutes and Josh only needed note cards for 30 minutes of it. Glen realizes that there’s more to a relationship than sex.

Later, Glen tries to talk to Miss Burko before they make love yet again. None of his prepared questions work out and she insists on getting down to business.

In English class the next day, Josh is doing a stand-up act for his classmates and it’s a big hit. Glen shows up at the first floor window, yelling for his former teacher. She dismisses the students early because she thinks he’s there for a “surprise matinée.”

Through an ensuing conversation, Glen admits that he doesn’t love Miss. Burko and she admits the same. He can’t understand then why they’re having sex. She explains that they’re apparently looking for different things in the relationship. As they bring their relationship to a close, Miss. Burko finally gives Glen a grade for his sexual abilities — a B+ — and proudly tells him he has the potential to be a great lover one day. He tells her the same which doesn’t really thrill her.

At his job at the video store, Glen’s still very pleased about his grade when Alison stops by. She admits that she sees something different in him and Glen admits that he’s “been promoted.”

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Alison seems bothered and admits that she and Gary broke up. Glen is honestly sorry and tells her that he hates to see her so sad. She’s touched by his compassion. As the episode credits start to roll, Alison tells him that Josh is going out with Wendy later and that she could use some company. She asks Glen if he’d like to grab some dinner later. He very happily agrees. His coworker Richard (Amir Talai) overhears and yells “Mazel Tov!” Glen and Alison smile at one another as the scene fades to black. End of show.

It’s the start of Glen’s dream relationship. Would he end up with Alison? How would Glen eventually become such a big success, becoming the richest man in Buffalo, New York? Sadly, we’ll probably never know. Stay tuned!