|During Jeff's first week at Greendale, he met fellow Spanish 101 student Abed Nadir and tried to get the attention of another classmate named Britta Perry. This involved forming a fake Spanish study group which backfired on him when she invited Abed and he in turn invited Annie Edison, Shirley Bennett, Pierce Hawthorne and Troy Barnes. He also attempted to convince his former client Professor Ian Duncan to help him cheat on his classes. Despite Jeff's best efforts he was unable to manipulate either situations to his favor. Exposed as a fraud to the study group and taught a lesson in cheating by Duncan. While he contemplated his next move, he crossed paths with the study group who took pity on him and allowed Jeff to rejoin them ("Pilot").
Jeff became the de facto leader of the group much to Britta's annoyance. They were all charmed by him particularly Pierce who wanted to be his best friend. When the Spanish teacher Ben Chang paired up the class for an assignment Jeff tried to become Britta's partner. Instead he wound up with Pierce who attempted to turn the simple assignment into a big production. After wasting several hours, Jeff left Pierce to join Britta at a protest she was attending. A drunk and angry Pierce showed up and made a spectacle of himself. The next day in Spanish class, Britta guilted Jeff into doing the presentation with Pierce. Jeff made up with Pierce but despite all of the pomp and circumstance in their presentation they ended up getting an "F" ("Spanish 101").
Jeff signed up for an Accounting class taught by taught by Professor Eustice Whitman believing it was an easy "A". Whitman was influenced by a certain movie and Jeff unexpectedly found himself struggling with his assignment to "Seize the day". At the same time he got wrapped up in family drama between Britta, Abed and his father's. She encourages Abed to take a film class over his dad's wishes. As part of a film assignment Abed cast Jeff and Britta as his mom and dad in a documentary he was filming. He later showed the completed projected to Jeff, Britta and his father which convinced Gobi to allow his son to pursue his dream. As a reward for helping her and Abed, Britta kissed Jeff in front of Whitman who declared he finally passed his assignment ("Introduction to Film").
A disciplinary tribunal consisting of Dean Pelton, Duncan and Chang was held in Borchert Hall to deal with Britta who admitted to cheating on a Spanish test. Jeff volunteered to represent her but found his efforts hindered when she confessed her guilt. During recess she accused Jeff of only wanting to help her so she would sleep with him. Jeff admitted it was part of the reason but his main focus was trying to help a friend not get expelled. Britta revealed getting caught was intentional as she was driven by her fears of inadequacy. Jeff used her damaged psyche as her new defense and got her sentenced reduced to a one years worth of mandated therapy sessions from Duncan. Afterwards, Britta begrudgingly thanked Jeff as they watched Pierce perform the new school song on the quad ("Advanced Criminal Law").
When Jeff refused to be a part of Greendale promotional materials he got blackmailed by Dean Pelton to recruit Troy for the football team. Annie was upset when he succeeded and Jeff pointed out that she just selfishly wants Troy all for herself. Annie countered that maybe true but unlike Jeff she genuinely cares for Troy. Later, Jeff went to the gymn where the football pep rally was being held. Jeff confessed to Troy how he manipulated him into becoming a quarterback again. Troy didn't care as the team was so horrible it allowed him to play for the love of the game free of pressure. Outside the gym Jeff ran into Annie who showed up to support Troy and apologized for his actions. They were interrupted by Pelton and Pierce who introduced the school's new mascot ("Football, Feminism and You").
Eventually Jeff moved on from wooing Britta and set his sights on his Statistics professor Michelle Slater. She refused due to the impropriety of dating one of her students. Undeterred, Jeff convinced Chang to get him into a faculty Halloween party Slater was attending. This meant ditching a "Dias De Los Muertes " party Annie was hosting where he was to be the guest of honor. Jeff was rejected again by Slater mostly due to the study group crashing the party. Once he sent his friends away he took advice from Chang and won Slater over. They were about to leave campus together when Jeff was told by Troy that Pierce needed his help. Jeff reluctantly ended his plans with Slater to see to the emergency. After it was resolved he stayed for Annie's party and danced with her to make up for his abscence earlier ("Introduction to Statistics").
Jeff was thrown out of his condo after he failed to make payments on it. He was forced to live out of his Lexus which was discovered by Shirley and Britta. When his car was towed away he accepted an offer from Abed to move temporarily into his dorm room. Unfortunately his stay had a negative affect on him as he became too complacent and unfocused. Abed noticed his personality shift and asked Britta to help to get Jeff back to normal. Britta snuck into Jeff's condo and retrieved his expensive Italian faucets heads. She gave it back to Jeff to remind him of who he was and to snap him out of his funk. Jeff was motivated enough to clean up and find a place of his own. He caught up with Abed and Britta at a campus concert and thanked them for their help ("Home Economics").
Jeff was bribed with a faculty parking spot if he agreed to partner with Annie for an intercollegiate debate against City College. His poor performance almost lost them the match but Greendale got a reprieve due to a scheduling conflict. It wasn't until the opposing debater Jeremy Simmons bullied Annie that Jeff took the contest more seriously. He studied with Annie which caused an unexpected sexual tension between them to flare up. At the rescheduled second half of the debate, Team Greendale pulled a commanding lead. A desperate gambit by Jeremy caused Annie to counter with her own unorthodox response. She kissed Jeff to prove her point resulting in the judges declaring Greendale the winner. Afterwards Jeff awkwardly congratulated Annie who suggested he just pat her before he left ("Debate 109").
"The Politics of Human Sexuality": Jeff hooks up with Dean Pelton's newest assistant Sabrina Shmuckle.
"Comparative Religion": Jeff takes on the school bully Mike over Shirley's objections.
"Investigative Journalism": Jeff is made the editor of the school newspaper and must also deal with a student named Buddy who wants to join the study group.
"Interpretive Dance": Jeff commits to an official relationship with Michelle Slater when it's revealed they had been secretly seeing each over Winter Break.
"Romantic Expressionism": Jeff and Britta conspire to break up Annie and Vaughn.
"Physical Education": Jeff butts heads with his new Billiards class teacher Coach Bogner over having to wear gym shorts to class.
"Basic Genealogy": Slater breaks up with Jeff causing him to seek out a rebound conquest which he finds in the form of Amber, Pierce's ex-step-daughter.
"Beginner Pottery": Jeff takes Pottery as a blow off class but ends up actually caring about it when he finds a rival named Rich who becomes the star of the class.
"Contemporary American Poultry": Jeff finds himself on the outs with the study group when Abed assumes control using them in his Chicken Finger Association.
"The Art of Discourse": Jeff and Britta face off against three obnoxious High Schoolers.
"Modern Warfare': Jeff and Britta reach a turning point in their relationship while they and the study group compete in the annual campus paintball assassination game.
"Pascal's Triangle Revisited": Michelle Slater and Britta compete with each other over Jeff's affections.