Living... in his car in the Greendale Community College parking lot. Recently disbarred and running out of money, Jeff enrolled at Greendale to set himself on a path to redemption, one easy credit at a time.
Profession... disgraced defense attorney turned community college student. He can no longer talk judges out of handing out harsh DUI sentences, but he can use his gift of gab to convince his professors to take it easy when they grade his half-assed papers.
Interests... shopping at the Gap. And slowly but surely, he is also starting to take an interest in the happiness of his Spanish study group members. What started as a scam to spend time with his classmate Britta turned into a real study group and – in a real shock to Jeff – a handful of actual friendships.
Relationship Status… single and lusting after his Spanish classmate, Britta. As a cynical psychology major, Britta sees right through his phony pickup lines until she starts to fall for him. And she’s not the only one – their classmate Annie and a few teachers also give in to Winger’s moves.
Challenge... getting his job back. But to do that, Jeff doesn’t just need a degree – he needs to grow as a person, too. That means not being so emotionally distant and opening himself up to his friends for help. Everyone at Greendale is there because they messed up one way or another and they’ve got no choice but to fix their problems together.
Personality... manipulative, self-centered, and power hungry. Jeff has conditioned himself to be a textbook narcissist in order to succeed, but at least he’s self-aware. “I always know what I’m doing is wrong,” he tells his friends, who eventually teach him there’s more than one way to get what you want. Thanks to this group of misfits, he becomes more understanding, more empathetic and more of a human being every day.
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