Jeffrey Tobias "Jeff" Winger (played by Joel McHale) is a graduate of Greendale Community College and currently a Professor of Law at the school. He was born in Denver, Colorado to his parents William Winger and Doreen Winger née Fitzgerald. His father divorced his mother when he was very young and would go on to have another child named Willy Junior. As an adult, Jeff became a very successful defence attorney specializing in DUI/DWAI/DUID cases, traffic offences, and juvenile crimes for over six years. He worked for a law firm called Hamish, Hamish & Hamlin that was founded by Ted. At work, he was often partnered with another lawyer named Mark and the two were known as "Tango & Cash" respectively. A drunk driving case Jeff handled involved a Psychology Professor named Ian Duncan with whom he became good friends. At the height of his success at the firm, Jeff's fraudulent academic credentials were exposed by a colleague of his named Alan Conner. Jeff was disbarred with his license suspended until he earned a legitimate degree. For four years he went to Greendale Community College with this goal in mind. During this time, he became close friends with a study group he formed. After having earned an Associate's degree in Education, he briefly returned to practicing law and started his own law firm. It was unsuccessful and he returned to Greendale where he accepted an offer to teach Law. He was also reunited with his study group and joined a special "Save Greendale Committee" to improve campus life.
I'm no sociopath. I always know what I'm doing is wrong. I'm just a guy that doesn't like taking tests, doing work, and getting yelled at. So if you think about it, I'm the sanest person here.Jeff
Jeff possesses a sarcastic wit along with a vain and egotistical personality. This is due to his mother having over praised him as a child . He claims to be Agnostic  but this can be seen as an example of his tendency not to put any effort into anything. His charming personality and persuasiveness are traits which served him well when he was an attorney. As a child he admired the divorce lawyer hired by his parents because he did his job without letting his personal feelings get in the way . This, along with an unfortunate incident with a bully named "Big Cheddar"  helped shape the more negative aspects of his personality. Jeff hates talking about his feelings and tries to maintain a facade of detached aloofness. His frequent avoidance of such emotional conflicts often results in moments of vulnerability . Usually, he tries to keep people at a distance and avoids opening himself up to others . This can be tied into his father's abandonment of him at an early age . However, Jeff's time with the study group has been a more positive influence and he's been honest about appreciating his time at the school . Although his study group originally tended to look to Jeff as their leader, they eventually began to rely on him less in this role.
After his law firm discovered that Jeff's bachelor's degree was falsified, Jeff was disbarred. He enrolled at Greendale Community College to earn a legitimate degree. He hoped to exploit his friendship with a professor who worked there, Ian Duncan, in order to secure an easy graduation. Another student named Britta Perry caught his eye and he pretended to be the head of a Spanish study group to impress her. Unexpectedly, a real study group is formed with other members of his class thanks to Abed Nadir. Jeff became the reluctant leader of the group and together they dealt with the unusual college life at Greendale. Jeff also had to contend with a few romantic troubles throughout the year. This included dating his Statistics professor Michelle Slater, an unexpected attraction, and his continuing flirtation with Britta. His relationship with Britta reached its climax at the annual Paintball Assassin game when they had sex. This resulted in a love triangle showdown at the Transfer Dance Formal at the end of the school year. Michelle and Britta both publicly declared their love for him and Jeff found himself unable to choose. Jeff left the dance without answering either of them only to complicate matters further. He ran into Annie outside the dance and after commiserating over their respective relationship troubles the two shared a moment and ended up kissing.
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 situation in 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 and the Study Group.
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. However, despite all of the pomp and circumstance in their presentation, they ended up getting an "F" ("Spanish 101").
Jeff and Pierce finished their presentation.
Jeff signed up for an Accounting class 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 Abed and his father. Britta encouraged 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 project to Jeff, Britta and his father which convinced him 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").
Sometime later, Jeff and Shirley unexpectedly bond over their love of gossip and making fun of their fellow students. He is also learned about Britta's new boyfriend, the campus hippie named Vaughn Miller. At Britta's insistence, Jeff put aside his jealousy and tried to be friends with him. When Britta showed Jeff a love poem Vaughn wrote to her, he shared it with Shirley and accidentally the rest of the study group. Vaughn found out and dumped Britta who was angry Jeff betrayed her confidence. Shirley and Jeff decided not to hang out anymore as all their gossiping and mocking wasn't good for either of them. She does tell Jeff he still has a chance with Britta who had a sex dream about him. Later, Jeff apologized to Britta who accepted as she came to understand the tough spot she put him in ("Social Psychology")
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 defence and got her sentenced reduced to one year's 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's 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 may be true but unlike Jeff, she genuinely cares for Troy. Later, Jeff went to the gym 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 Muertos" 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 absence 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 effect 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 faucet 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").
Well, I only ever liked one person: my mom. And she liked my dad. And after all the dust and custody was settled, the guy I really admired--admired not liked, mind you--was the lawyer leaving the courthouse in a great-looking suit and a sky-blue Mercedes SLK.Jeff, "Accounting for Lawyers".
School year synopsis
On Jeff's return to Greendale for the study group's second year together, he immediately had to deal with repercussions from his actions at the Tranny Dance last semester. Jeff is forced to reevaluate his goals after a brief return to his former life. Among the various escapades and hijinks, he had with the study group, Jeff dealt with his complicated feelings for Annie, his increasingly acrimonious relationship with Pierce and a secret affair he was keeping from the study group. He ended the school year participating in a second Paintball Assassin game where his issues with Pierce came to a head. During the contest, Pierce quit the study group just as the paintball contest itself escalated. Greendale's rival school City College interjected themselves into the competition which led to Jeff and Troy gathering the remaining players and forming an alliance against the interlopers. Under their leadership, a two-pronged assault was launched against the paintball invaders. Jeff was eliminated while leading a squad of students to take down the Paintball Gatling gun. Ultimately, Pierce won the paintball contest and saved the school much to Jeff’s shock. Afterwards, Jeff and the study group agreed to forgive Pierce for his past behavior. Jeff personally invited him to rejoin them next semester but Pierce refused and declared he was done with the group.
In the study group's third year at Greendale, Jeff started the new semester off on the wrong foot with his latest teacher, Professor Marshall Kane. He also spent his year in therapy having dealing with his daddy issues, facing his complicated feelings for Annie, discovering a shared past he had with Shirley, and negotiating a peace between the warring factions of Pillowtown and Blanketsburg. When the Biology class was cancelled before the end of the school year, he and the group are forced to lose their credits and retake the class. In anger, they instigated a riot in the cafeteria which led to them all being expelled. They redeemed themselves when Jeff and the group save Greendale from the rule of its new overlord Ben Chang. They are all reinstated but Troy is forced to join the Air Conditioner Repair School and told never to see his friends again. Despite the loss, Jeff and the rest of the group retake Biology during the summer. On the day of the final exams, he was asked to represent Shirley against Pierce in a Greendale Summer Court case over the title of ownership for their joint business venture "Shirley's Sandwiches". He faced off against Pierce's representative, his former law firm colleague Alan Conner. Alan bribed him with his old job at the firm to throw the case. Instead, he resolves the dispute amicably with a "Winger Speech". In retaliation, Alan told Jeff he was responsible for getting him fired. Jeff already knew and thanked him as he sincerely appreciated his time spent at Greendale.
"Biology 101": On his first day of school, Jeff gets kicked out of the study group's latest class by angering the teacher, Professor Marshall Kane. While trying to get back in class he gets sprayed by monkey gas which temporarily makes him unstable. Feeling abandoned by the study group he confronts them in Group Study Room F and attempts to destroy the study table with an ax. Pierce later takes the blame for his behavior and Jeff is forgiven by the group. He also makes amends to Professor Kane and is allowed back into class.
"Remedial Chaos Theory": While at Troy and Abed's housewarming party for their new apartment, Jeff proposes the roll of a Yahtzee die to determine who should go downstairs to get the pizzas from the delivery guy which creates six different scenarios.
"Foosball and Nocturnal Vigilantism": Jeff and Shirley team up to take down German exchange students hogging the Foosball table and discover they have a shared past. She bullied him when they were kids and beat him in a game of Foosball. She further humiliated him by causing him to pee his pants after jabbing him with a Foosball shaft. He forgives her after realizing she truly regrets what she did and has since changed for the better.
"Contemporary Impressionists": Jeff sees a new therapist who over medicates him with anti-anxiety pills. This leads to an ego field rampage at a Bar Mitzvah which sees him being shot by Ben Chang with a tranquilizer gun.
"Urban Matrimony and the Sandwich Arts": Jeff struggles to write a toast for Shirley and Andre's upcoming nuptials. At the rehearsal dinner, he and Britta get drunk and try to convince the pastor to marry them.
I'm just a grown man who can't look his own friends in the eye for too long because I'm afraid that they'll see that I am broken.Jeff telling his father how badly his leaving affected him, "Cooperative Escapism in Familial Relations".
School year synopsis
In the study group's fourth year at Greendale, Jeff is actually eager to start the year. He reveals to everyone that he is only a few credits shy from graduating having taken additional courses online over the summer. He is forced to participate in a competition called "'The Hunger Deans" in order to secure spots for each of the study group members in a class they all signed up for. In his personal life, Jeff finally gets closure with his father issues. He reunites with William Winger on Thanksgiving Day and also is introduced to his half-brother Willy Jr. whom he bonds with over how poorly their father treated them. He has a similar bonding moment with Pierce after he agreed to go to an old-fashioned barbershop with him. He also investigated Ben Chang's claim of amnesia when he returned to school. He continues to open up to the study group even sharing with them his most shameful secret and owned up to his past misdeeds. After passing his History class, he gets enough credits to graduate and starts to feel anxiety over leaving his friends to return to his former life as a lawyer. He imagines a scenario involving "The Darkest Timeline" which ends up reaffirming that he is no longer the selfish guy he was when he started at school. Later at a graduation ceremony thrown by his friends, he thanks them for changing him for the better.
"Heroic Origins": Jeff learns that the first big case he won as a lawyer involving a stripper named Mysti which cost him his job also might have accidentally led to the end of Shirley and Andre's marriage.
I'm not becoming a teacher Abed, that's lame.Jeff, "Repilot".
School year synopsis
After a law firm he started goes under, Jeff is reunited with the study group for another year at Greendale Community College. He accepts a teaching position at school as the new Law professor. He and the study group join a "Save Greendale Committee" tasked with bringing harmony to the school's campus. Jeff and Annie investigate the campus menace known as the "Ass Crack Bandit" which comes to an abrupt end when they learn of Pierce Hawthorne's death. After attending his funeral, Jeff and the group submit to a private inquest into Pierce's death stipulated by his will. For his participation, he is bequeathed a bottle of fine scotch and a Liquid nitrogen cooled cylinder of Pierce's sperm. Jeff joins in a campus-wide game of "Hot Lava" hosted by Abed in honor of Troy who is leaving Greendale. Jeff and the Save Greendale Committee decorate the Mid Term dance with disastrous results. He later helps Duncan try to woo Britta and attempts to take down Shirley when an app makes her a bully again. Jeff later discovers a stash of possibly lucrative textbooks which he and the committee unsuccessfully try to fence. He joins the committee in trying to help Buzz reconnect with his son Hank through a game of Dungeons & Dragons. On his fortieth birthday, he takes anti-ageing pills and falls into a coma and imagined he was in a G.I. Joe cartoon. when Greendale is about to be sold to the Subway corporation, Jeff and Britta try to cope with the situation by becoming engaged. The two reluctantly join the rest of the committee in a desperate quest to save the school. During the quest, Jeff used his feelings for Annie to power an emotion fueled computer that freed him and his friends from an underground laboratory they were trapped in. After the committee is successful in stopping the sale of the school, Jeff and Britta officially call off their engagement.
You did it Jeff Winger. This is your school now.Jeff, "Ladders".
School year synopsis
Jeff returned for a sixth year at Greendale triumphant after having rescued the school from closing. However, a disaster the Save Greendale Committee failed to prevent led to Dean Pelton hiring a consultant named Francesca "Frankie" Dart. Initially, Jeff clashed with Frankie but eventually accepted her and inventor Elroy Patashnik into the group. He and the new committee dealt with an attack ad City College was going to air against Greendale, a program allowing convicts to attend school via tele-robots, having their personal emails released to the public by a hacker and getting drawn into yet another paintball conflict. Throughout the semester, Jeff became increasingly depressed and noticeably drank more alcohol. This led to an emotional breakdown where he admitted to Abed he feared he'd be stuck at Greendale alone as all his friends left him. He is forced to confront this possibility at the end of the school year. Both Annie and Abed announce they are leaving for the summer to pursue opportunities outside of Greendale. He had a conversation with Annie where he confessed his anxieties along with his true feelings for her. She convinced him to accept the pros and cons of his situation and they shared a brief kiss. Afterwards, he drove Annie and Abed to the airport and saw them off. He then went to The Vatican bar and shared a drink with the remaining members of the committee.
Jeff was considered the leader by default within the study group. As much as he made a show of lamenting this he inwardly embraced being in charge. Although at times he exploited his position more often than not he did right by the study group. In time he came to care greatly for them and even admitted they changed him for the better. When he became a teacher he became depressed at the thought of everyone leaving him behind while he stayed on as faculty. Eventually, he came to accept that they needed to go out and try to live in the real world away from the craziness of Greendale like he once did.
Jeff's aggressive pursuit of Britta in his first year at Greendale led to the formation of the study group. Initially, they considered themselves to be the group's parental figures but settled on just being their friends. They became lovers during their first year at school and during their second year began a secret friends-with-benefits relationship. Eventually, they mutually decided to stop the arrangement once their friends learned about it. Despite three separate occasions where they got engaged, they had a platonic and at times antagonistic relationship.
Annie was charmed by Jeff along with the rest of the study group and a mutual attraction bloomed after they shared an unexpected kiss. This underlying sexual tension continued throughout the rest of their time at Greendale. However, Jeff kept his distance from Annie, uncomfortable with the age difference. It wasn't until their sixth year together at school that he admitted how he felt and the two shared a brief kiss. She assured him that they might not have missed their chance by stating that future was not set. He later drove Annie and Abed to the airport for summer internships they had out of state.
Jeff met Abed first before the study group was formed. Initially he acted as Jeff's flunky but thus eventually became a more equal friendship. They briefly became roommates which further cemented the relationship. Like the rest of the study group, Jeff accepted Abed's odd behavior and was shown to be very protective of him. Abed is one of the few members of the group Jeff goes to for advice. After their sixth year at school, Jeff drove both Annie and Abed to the airport when they left Greendale for job opportunities out of state. Jeff hugged Abed twice before he departed.
As with the other members of the study group, Shirley has a mostly maternal relationship with Jeff. Although annoyed with her mother-henning and sermonizing, Jeff respected her beliefs and appreciated that she cared so much for her friends. In their third year at school, they learned about a shared history they had. When Shirley was 12-years-old she publicly humiliated a 10-year-old Jeff by making him wet his pants in a game of foosball. They have since made peace with the past and have become even closer. Jeff even stated that Shirley was the only one who understood him. Shirley has been shown to be one of the best influences on Jeff during his time at Greendale.
Pierce was at first in awe of Jeff as was the rest of the study group and tried repeatedly to become his best friend. He later became envious of Jeff's status in the group and often claimed Jeff was gay. Despite this, Pierce showed several times that he did care about Jeff and on rare occasions offered some helpful advice. Jeff and the study group would later mourn Pierce's passing and take part in a polygraph test which was dictated in Hawthorne's will.
Troy initially looked up to Jeff admired his way with women, particularly Britta whom he had a crush on. Jeff and Troy are the two most physical members of the group and sometimes compete in athletic contests. As Troy began to assert himself more Britta suggested Jeff felt threatened by him. When Troy left on his trip around the world he told Jeff he was the coolest person he knew. Jeff responded that Troy was actually cooler since he was leaving Colorado, something he himself had never done.
Years ago, when Jeff was still a lawyer for Hamish, Hamlin and Hamlin, he successfully defended Ian Duncan from DUI charges and the two become friends. This relationship is the primary reason Jeff decided to go to Greendale after he was disbarred for faking his credentials. He had hoped to exploit their friendship to cheat his way to a legit degree, which Duncan refused. Although Ian is at times as unethical as Jeff, he will sometimes try to teach him a lesson. The two remain friends and drinking buddies.
In Jeff's first year at Greendale, he romantically pursued his Statistics professor Michelle Slater. They started dating secretly but eventually were found out by his friends and Dean Pelton. A brief rough patch occurred due to a pair of drunk dials exchanged between Jeff and Britta. Despite forgiving him for the misunderstanding, she suddenly and unexpectedlydumped him. At the end of the school year, she admitted to Jeff she made a mistake. This led to a showdown between her and Britta for Jeff at the Tranny Dance. After they both declared their love for him, Jeff found himself unable to respond. Taking advantage of a distraction, he shared a look with Slater before exiting the dance.
The Dean has a crush on Jeff and always tried to make a move on him, often touching him inappropriately and talking suggestively to him. A few times the Dean will go too far such as when he blackmailed Jeff to spend the day with him at the mall. Although annoyed by his creepy advances, Jeff has shown to be somewhat fond of the Dean and even had fun on their "date" together. He has gone as far as forgiving Dean for his crazy antics on the set of a Greendale commercial he was filming and also hatching a plan to save Craig from Chang after he is kidnapped and replaced by Faux-by.
William Winger is Jeff's father who left him at a very young age. William is contacted by Jeff in his fourth year at school in order to confront his unresolved abandonment issues. They meet on Thanksgiving Day and after some awkwardness, they start to bond. However, a Jeff is infuriated when William suggests him leaving had a positive impact on his son. Jeff finally unloads all the animosity he's been carrying and tells William how badly his abandonment affected him. William feigns a heart attack but Jeff sees through the ruse and leaves finally having attained a measure of closure for the years of bitterness he felt towards his father.
Willy Jr. is Jeff's half-brother whom he met at the Thanksgiving dinner at his father's home. Willy grew jealous of the rapport Jeff quickly formed with William. However, Jeff left after their father made a thoughtless comment. Jeff drove away unaware that Willie Junior was hiding in the backseat. After revealing himself, he asked Jeff to teach him how to be aloof so their father will like him too. Willy made Jeff realize that suppressing his emotions is the same as letting their father off the hook for being a bad parent. After confronting William, Willy Jr thanked Jeff with a hug for saying what he couldn't to their father.
Jeff met Sabrina, Dean Pelton's new assistant, when she was helping the Dean with the STD Fair. She caught Jeff's eye and later, after some teasing from Pierce about his recent dating dry spell, he gets her to be his date. Unwittingly, Pierce tricks him into going with him and his new girlfriend Doreen on a double date to the STD fair. Although very attractive, she is too easily charmed and very immature as pointed out by Doreen to Jeff. Later that night, during a parking lot make-out session inside his Lexus, Sabrina's immaturity becomes too much of a turn off for Jeff and he loses interest in her.
Jeff has had multiple flings with other girls, including Amber, Pierce's step-daughter. Jeff tries to be a good friend to Pierce and not have sex with his step-daughter, but he eventually gives in. However, upon finding out that Amber is grifting Pierce, Jeff breaks things off with her.
In the study group's second year at Greendale, Annie develops a crush on Rich and suggests that he join the study group. In response Jeff finds Quendra and offers her as a better candidate. She walks out before a decision can be made after Pierce insultingly propositions her. At the end of the year paintball game, she joined Jeff's paintball assault squad on the City College machine gun placement. She was inspired by a stirring speech from Jeff only to be disappointed when he quickly changed his tune after getting eliminated.
Jeff's age in the Season Five episode "G.I. Jeff" is revealed to be forty. This information contradicts established canon that his age at the start of the show was around 35. It is possible he was lying the entire time, however this revelation conflicts with information in previous episodes as well as statements Community creator Dan Harmon himself had made early in the show's production. Below are several "Community" episodes which hint at Jeff's age.
"The Art of Discourse": in 2010 Jeff is called "35" by Mark Cahill and doesn't dispute it.
"Early 21st Century Romanticism": In 2011, Ben Chang steals Jeff's driver's license which clearly says "November 21, 1971" (this is actor Joel McHale's birthdate). On DVD commentaries for this episode and also in a tweet to a fan, Harmon dismissed this as a production error and suggested that Jeff was several years younger than him or Joel. At the time McHale was 40 and Harmon was 38.
"Intro to Political Science": In 2011, a videotape of Jeff's audition for "The Real World: Seattle" is shown. Jeff says he was "like 19" when he recorded that tape. The Real World: Seattle premiered on June 16, 1998, and if it followed the production schedule of other Real World shows, then it accepted audition tapes the previous year in 1997. This then suggests that Jeff was born around 1978. That puts Jeff's age at that time around 33-34. It should then make him 36-37 in Season Five.
"Foosball and Nocturnal Vigilantism": In 2012 Jeff claimed he was 10 years old when he met Shirley "Big Cheddar," who was 12 at the time. Either Jeff was lying and was small for his age according to how he looked in the flashback shown (14-15), or Shirley's age gets increased to 42. Incidentally, the child actor hired to play young Jeff (Jacob Bertrand) was 11 years old at the time.
"Cooperative Escapism in Familial Relations": in 2012, Jeff very specifically tells his father he faked an appendectomy in seventh grade "22 years ago." The average age of a seventh grader is between 11-13, older if Jeff had failed a grade and was held back or younger if he skipped a grade (unlikely as it would probably be something he'd brag about). This is consistent with previous episodes as it places his age at that time to be around 34-35 which would make him 36-37 in Season Five. Additionally, it's unlikely Jeff could get away with lying about his age to his own father.
Community writer and executive producer Andy Bobrow had a discussion with several fans on his Twitter account about this discontinuity:
“@Funkapus @SaraLinnLinn We try not to be sloppy. Try to make the characters as real as possible. Sometimes we screw up and everyone tells us.”
Chang lived with Jeff for a while after his wife kicked him out.
Jeff is left-handed, although he fires guns with his right hand.
Jeff has appeared in every episode of the show.
Jeff has kissed each of the female members of his Study Group: Britta in "Introduction to Film", "Modern Warfare", and "Anthropology 101", Annie in "Debate 109" and various other episodes and Shirley in "Contemporary Impressionists".
Jeff's character is at least partially based on Dan Harmon's own experiences in college, where he grew attached to his Spanish study group.