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In the Season One premier, Jeff Winger is introduced as a lawyer who lied about having a law degree from Columbia University, when in actuality, he had gotten his degree, mail-order, from the country of Colombia. He enroll's in Greendale Community College, hoping to use his friendship with the school's psychology professor, Dr. Ian Duncan, to his advantage. Unfortunately for Jeff, things don't work out the way he planned, and he is forced to become an actual student.
On his first day, Jeff meets Britta (a girl from his Spanish class) and convinces her to join his non-existent study group, hoping to get time alone with her. However, when Jeff shows up at the library later to meet Britta, he finds out that she has invited a cast of characters from their class to join them. Jeff continues to pursue Britta, but to no avail, as she discovers what he is up to, and he is asked to leave. Eventually the group forgives him, and he is allowed to return. ("Pilot" Season 1 Episode 1)
Jeff, still trying to beat the system, discovers that there is a professor who doesn't grade based upon merit of work, and enrolls in the class, only to discover that professor can instantly see what he is up to. The professor tells Jeff that if he doesn't actually learn to "live in the moment" then he will fail his class. Britta helps Jeff by kissing him in front of his teacher. ("Introduction to Film" Season 1 Episode 3)When the dean wants to get Troy to play for the football team, he blackmails Jeff into convincing Troy, by creating a number of Greendale Community College ads with Jeff in the forefront. ("Football, Feminism and You" Season 1 Episode 6)
Jeff tries to date his Statistics Professor, but she tells him that she doesn't date students. So, in attempt to get her attention, Jeff skips Annie's party and crashes the faculty Halloween Party. ("Introduction to Statistics" Season 1 Episode 7)
When Jeff can't afford the rent for his condo any longer, he begins living in his car. When the group finds out, they take pity on him, and after his car is impounded he moves in with Abed. Living in the dorm, makes Jeff more depressed and he begins to stop caring about both hygiene and life in general. Britta eventually convinces him that everything he stood for before really was worth it, by sneaking into his condo and stealing his hand-crafted, Italian bathroom faucets for him. ("Home Economics" Season 1 Episode 8)
When Annie convinces Jeff to join the debate team, to the surprise of both of them they find a mutual attraction to one another, which Annie uses to her advantage and wins the debate. ("Debate 109" Season 1 Episode 9)
Jeff who has been dating his Statistics Professor begins to freak out when she wants to take their relationship to the next level, and officially declare it to the school. However, he eventually discovers that he is ready for a serious, grown up relationship. ("Interpretive Dance" Season 1 Episode 14)
When his girlfriend dumps him, Jeff tries to act like he is okay with it. ("Basic Genealogy" Season 1 Episode 18)
When the school hold a paintball tournament for priority registration, it pits all of the cliques against each other. Eventually Jeff and Britta are the only ones left, and their sexual tension finally gets the best of them. To end the tournament, the dean sends in Señor Chang, an expert paintballer to take out the remaining players, yet Jeff still comes out victorious. ("Modern Warfare" Season 1 Episode 23)
Jeff's ex-girlfriend tells Jeff that she regrets breaking up with him and wants to get back together, but this drives Britta mad, so she reveals to Jeff (and the entire school) that she is in love with him. So, when Jeff can't handle the pressure anymore, he runs away and ends up locking lips with Annie. ("Pascal's Triangle Revisited" Season 1 Episode 25)
- "The state bar has suspended my license. They found out my college degree was less than legitimate." ("Pilot" Season 1 Episode 1)
- "The truth is my life is emptier than this three ring binder. Annie, do you have any Spanish notes that might fit in there? Double spaced? Thank you. What's a guy gotta do to get a "C" around here?" ("Spanish 101" Season 1 Episode 2)
- "The woman I kind of like is out there in the moonlight caring about something stupid. This my chance to show her I care enough to act like I care about it too." ("Spanish 101" Season 1 Episode 2)
- "You're just as selfish as I am. You're just not as good at it yet." ("Football, Feminism and You" Season 1 Episode 6)
- "Can't I be the friend in the group whose trademark is his well-defined boundaries like Privacy Smurf, Discrete Bear or Confidentiality Spice?" ("Interpretive Dance" Season 1 Episode 14)
- "...And tell the drama club their tears will be real today." ("Modern Warfare" Season 1 Episode 22)