Alan Conner is a lawyer and former co-worker of Jeff's from his old law firm, "Hamish, Hamish & Hamlin". He reunites with Jeff at Greendale when he shows up to the school for a N.A. meeting. As a successful attorney, he is respected for his skill inside the courtroom and reviled for his hedonistic nature outside of it. Despite his jovial demeanor, he possesses a ruthless side and is shown to be quite an opportunist. His first appearance was in the Season Two episode "Accounting for Lawyers" and he made his return in the Season Three episode "Introduction to Finality". He is portrayed by actor/comedian Rob Corddry.
In the study group's second year at Greendale together, Jeff is unable to take the latest weird happenings at the shcool and leaves to clear his head. Accompanied by Abed, he goes to the student lounge where he runs into his old law firm buddy, Alan Conner. Abed misreads Jeff's reluctance to see his former colleague and calls out to Alan, forcing Jeff to say hello. Surprisingly, Alan greets him warmly. Although embarrassed about his current situation, Jeff admits he is a student at the school. Alan says he's not one to judge since he's at the school for a Narcotics Anonymous meeting being held on campus. He then asks Jeff if he wants to grab a drink. Abed reminds Jeff he has class, but Jeff blows it off and leaves to catch up with his old friend.
For the next few days, this becomes a regular occurrence as the study group begins to see less and less of Jeff. One day he shows up to a group meeting late with Alan in tow. He introduces him to the group and Alan starts to flirt with Annie who seems to recognize him. Alan ends up but making a bad impression after he trades insults with Pierce. Jeff is amused at the exchange and the pair leave to get a drink at a nearby bar. This reaffirms the group's earlier fear that Alan might be a bad influence on Jeff. At the bar, Jeff and Alan are reminiscing about their time at the firm. Jeff admits he misses his old life and Alan suggests that he come visit the office. Jeff is reluctant feeling that the scandal surrounding his dismissal made him a pariah. However, Alan informs him it did the opposite as his fake law degree made him something of a legend.
Alan then invites Jeff to an office party taking place at the law firm. Meanwhile, Annie remembers why Alan was seemed so familiar, she met him when she attended her Narcotics Anonymous meetings for her Adderal addiction. She also recalled that he had bragged about getting a colleague fired by ratting him out to the state bar. She tells the study group Alan may have been the one who had Jeff disbarred. When Jeff returns, the group tells him but he considers the evidence circumstantial at best. Angered they would accuse his Alan and claiming to fell stifled by their friendship, Jeff declares he is taking a break from them and attending the office party instead of going with the group to compete at the Pop and Lock-toberfest dance off. Annie then contacts Alan and gets him to invite her and the study group as well.