|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 spots an old law firm buddy of his named Alan Conner. Although reluctant to say hello, Abed forces his hand and Jeff reluctantly greets his former colleague. Alan is happy to see him didn't give Jeff grief over having to reenroll at school. He pointed out he himself was on campus to attend a court appointed Narcotics Anonymous meeting. Over Abed's objections, Jeff blows off class and joins Alan for a drink. For the next few days, this becomes a regular occurrence. Jeff misses several study group meetings reconnecting with Alan. When Jeff eventually introduced his friend to the group Alan made a bad impression after he traded insults with Pierce.
The two went to a bar where Alan mentioned Jeff's his fake law degree made him something of a legend amongst his former peers. Alan then invited Jeff to attend party at the law firm. Back at school, the group feared the bad influence Alan had on Jeff. Annie eventually recognized him as someone she met years ago at a N.A. meeting. She also remembered Alan bragged about getting a colleague fired after ratting him out to the state bar association. They confronted Jeff with their suspicions but he ignored their warnings. That night he went to the office party with Alan instead of the pop and lock contest he and the group were entered in. After the head of the firm Ted gave a speech, Alan admitted to Jeff he invited him with an ulterior motive in mind.
Alan hoped Jeff could talk to Ted about making him partner at the firm. Their conversation was interrupted when the study group arrived at the party. Alan had invited them as well since Annie caught his eye when they were briefly introduced. Alan took her aside and flirted with her as Jeff tried to get his friends to leave. When Annie excused herself, Alan caught up with Jeff who was reacquainting himself with Alan. He awkwardly inserted himself into the conversation but Ted was unresponsive to his attempt at humor. Alan left them alone to talk some more which actually produced some surprising results. After his chat with Jeff, Ted made Alan a full partner. Alan thanked Jeff who wanted to return the favor by revealing who at the office ratted him out to the state bar.
Jeff had already gotten confirmation from the study group that Alan was the one in the form of a copy of the e-mail. He was not surprised when Alan lied and told him it was lawyer named Thompson. Jeff pointed out that seemed unlikely since Thompson was a straight arrow. He adopted three at risk teens, donated his liver to a temp worker at the firm and left the firm when Jeff was fired after his wife died. However, Alan stuck to his story and Jeff congratulated him on his promotion nontheless. Alan invited Jeff to join him at the bar for shots to celebrate but he declined. Jeff stated he "caught something" at Greendale and needed to go but Alan misunderstood that to mean he was going to go after some college coeds ("Accounting for Lawyers").
In the study group's third year at Greendale, Shirley and Pierce have a falling out over their business venture "Shirley's Sandwiches". Pierce hired Alan Conner to represent him in a faux court case to win sole ownership of the business. Jeff had volunteered to represent Shirley in the faux trial and was shocked to see his old colleague there. The two discussed the ridiculousness of the situation and made an agreement to finish the trail as fast as possible. Alan also assured Jeff he would go easy on Shirley when he cross examined her. ("Introduction to Finality")
Sometime after the study group graduated, Alan Conner had a proposal for Jeff.