When Annie first meets Jeff, she is immediately suspicious of his credentials as a "board certified tutor" in Spanish but is eventually charmed by him along with the rest of the study group. Despite pursuing other members of the study group, the two discover to their surprise that they are both attracted to each other. They share a kiss during a debate competition which leads to another one at the end of the year outside the Tranny Dance. This creates an underlying tension between them throughout the rest of their time at Greendale. Jeff initially tries to keep his distance from Annie as he is uncomfortable with the age difference. Although Jeff has become a bit more honest about how he feels towards her he has yet to clarify to himself or to her what those feelings actually mean. Jeff is portrayed by Joel McHale, and Annie is portrayed by Alison Brie.
After forming a fake study group to impress Britta, Jeff is surprised when Abed invites a number of other students to join them. Annie shows up and is eventually won over by him along with the rest of the study group. They bond after confronting each other over selfish reasons they have for trying to manipulate Troy. Later, the two discover an underlying attraction in the episode, "Debate 109", when Jeff and Annie compete against Greendale's rival school City College in a championship debate. She kisses Jeff in order to win, causing them to have an awkward sexual tension. The U.S.T is hinted at in various episodes, subtly leading up to the finale. A heartfelt conversation about their respective romantic troubles results in Jeff and Annie sharing a second kiss outside of the Tranny Dance.
Jeff tries to deal with the fallout from the Tranny Dance and makes it clear to Annie that the kiss was a mistake. Despite his denial that it meant anything, there are moments throughout the season which hint otherwise. Annie struggles with her feelings for him as well even after expressing her disgust over his behavior and claiming to Britta that she only kissed him to be cool. Although they drift apart at the beginning of the year, they find themselves drawn back together as Jeff helps Annie uncover a conspiracy, searches for her lost pen, and becomes jealous over a crush she has on Rich. Towards the end of the year, things start to become rocky between them again. Although they only briefly clash when they both run for student body president, a revelation by Abed about Jeff and Britta's casual hook ups throughout the semester is harder to resolve. An upset Annie confronts Jeff about the flirting that had been going on between them while this affair was happening. Jeff strongly denies it and asserts that just as many moments could be found with any random pairing in the study group. Abed refutes Jeff's claim and states whatever is going on between them is more significant then he is willing to admit. The year ends with them arguing about whether Pierce should be allowed to stay in the study group and Annie kissing Abed during that end of the year paintball competition.
Listen, when you really hate someone the way you hate Annie Kim or you feel the way I feel about you, the easy loophole through the creepiness and danger is to treat them like a child. 'Chip off the old block!', 'You're the best kiddo!' It's a crutch, it's a way for me to tell you how important you are from a distance. But now you're becoming this mature, self-possessed, intelligent, young woman and I can't keep patting you on the head or talking down to you.
The third year sees Jeff in therapy and now slightly more honest about his feelings towards Annie. A Model UN showdown with Annie's rival unexpectedly leads to a frank discussion between the two of them about their relationship. Although they spent the year still unsure of where they stand, they continued to have flirtatious moments throughout their latest semester at Greendale; there were even a few significant ones in other timelines. They also manage to partner up on several occasions including helping out with the Glee club, trying to find a student named Kim McFadden whom Jeff offended, exchanging texts during the drawn out Pillows and Blankets War, and prosecuting Todd for sabotaging their Biology lab experiment.
"Regional Holiday Music": Annie tries to persuade Jeff to join the Glee club by putting on a private performance for him.
"Urban Matrimony and the Sandwich Arts": When Jeff is trying to write a speech for Shirley's wedding, he turns to Annie for advice. When given a look into Jeff's heart (at Annie's suggestion), we see multiple pictures of Annie.
""Virtual Systems Analysis": Annie rejects Abed's analysis of her relationship with Jeff but admits she had selfish motivations behind their kiss at the Tranny Dance, and would have considered it "a bonus" to have gotten together with Jeff if Troy and Britta began dating.
The fourth year of the study group at Greendale sees Jeff looking to graduate early which upsets Annie. During Halloween, a text message miscommunication sees the pairing costume Jeff had planned with Annie ruined when she shows up dressed as the girl from The Ring. During a weekend trip the study group takes to an "Inspector Spacetime" convention, Jeff and Annie's plans to go skiing fall through. Jeff decides to leave but Annie elects to stay behind and take advantage of his hotel rooms perks by pretending to be "Mrs. Winger". She creates an elaborate scenario imagining what it would be like being married to him. Before Jeff graduates, he entertains some fantasies himself about Annie when he imagines their evil counterparts from "The Darkest Timeline" canoodling and plotting to destroy the "Prime Timeline".
"History 101": Annie is hurt that Jeff kept the fact that he is graduating early a secret from the study group.
"Paranormal Parentage":Jeff and Annie plan a pairs Halloween costume with Jeff as a boxer and Annie meant to be a ring girl.
"Intro to Knots":Annie redecorates Jeff's apartment after inviting Professor Cornwallis to the study group's Christmas dinner party Jeff is hosting there. In the episode end tag, The Darkest Timeline is shown and Evil Jeff frees Evil Annie from Greendale institution for the criminally insane.
"Advanced Introduction to Finality": Jeff daydreams a scenario where the Darkest Timeline counterparts to himself and Annie cross over into the Prime Timeline and try to corrupt him.
I've enjoyed our game of cat and mouse. It's funny how close your two little helpers get to catching me. I liked watching them run in circles. Although sometimes I wonder, are they chasing me as an excuse to get near to each other? I mean, get a room already.
Jeff and Annie, along with the study group (sans Pierce), reunite for an unexpected fifth year at Greendale. Jeff accepted a teaching position at school and Annie enrolled to get a degree in Criminology. She joined Jeff's Law class to ensure he took his job seriously. The two team up to catch the mysterious assailant known as the "Ass Crack Bandit" and when Abed hosts a campus wide game of "Hot Lava". When the committee plays a game of Dungeons & Dragons they end up in the same party as Buzz. On Jeff's fortieth birthday, he over medicates, slips into a coma and imagines himself along with Annie and their friends as characters in a G.I.Joe cartoon. After the Greendale school board sells the school to the Subway corporation, a depressed Jeff rashly gets himself engaged to Britta. Although greatly upset by this, Annie she lets him know that she will accept and support his decision. When the two join the rest of the committee on a quest to save the school, they all end up trapped in an underground secret computer laboratory. Jeff is told a strong "burst of passion" into an emotion processing computer called "Raquel" could cause the lab doors to open. Jeff voluntarily hooks himself up to the machine and fulfills the requirement after looking at Annie. The gang escapes and Jeff stops Greendale's sale with a legal loophole he discovered while in the lab. With the crisis resolved Jeff and Britta mutually call off the wedding. Afterwards he and Annie attend a Save Greendale Committee where they all celebrate saving the school.
"Geothermal Escapism": Jeff and Annie form an alliance when Abed hosts a campus wide game of "Hot Lava".
"Basic Sandwich": Annie tells Jeff she will sport whatever decision he makes about marrying Britta. When the gang gets trapped inside Russell Borchert's lab, Jeff uses his feelings for Annie as a catalyst to power up an emotion fueled computer in order to free them.
At the start of the show, Jeff and Annie were meant to have a more fraternal dynamic between them although it was hinted that Annie had a small crush on him when they began their signature exchange to each other, "Milady/Milord" ("Spanish 101"). The age difference was established in order to reinforce the idea of the older brother/little sister relationship ("Football, Feminism and You"). It had already been made clear who their intended love interests were to be at the start of the show. Jeff was pursuing Britta, and Annie had a huge crush on Troy ("Pilot"). However, the writers slowly began to notice their onscreen chemistry in the few scenes they had. In this interview and on DVD commentaries, creator and showrunner Dan Harmon mentioned how he had decided to add a romantic element to their dynamic to acknowledge that rapport. He had the episode "Debate 109" make an attraction between them canon which was well received. AV Club critic Todd VanDerWerff at the time the episode aired named it the best one yet making a note of Alison Brie and Joel McHale's chemistry (source). The popularity of the pairing increased and the new dynamic between them created a long running sexual tension which has fueled most of their interactions on the show. It also inspired a sizable following online which is still active today (see Fandom). In the DVD commentaries for Community The Complete Fifth Season, Dan Harmon confirms that Jeff loves Annie. He clarified that it was Jeff's passion for Annie that opened the door to Borchert's lab in "Basic Sandwich".
I think when we see Jeff and Annie together, there's such natural chemistry between Joel and Alison, there's never any question that those two characters have the strongest heat between them. Our discussions in the room are never about whether there's something strong between Jeff and Annie, they're about what we do with that something and what makes the best television.
Jeff and Annie represent an opposites attract type pairing. Although they often clash over opposing viewpoints, they are usually able to resolve most conflicts between them easily. They have also teamed up effectively on a number of different occasions and have shown to complement each other quite well in each instance. The age difference, which was originally hinted to be 12 years and now has been retconned to 17, has been something that clearly bothers Jeff. This is evidenced by his reactions in "Anthropology 101" and "Asian Population Studies" and continues to be an issue Jeff struggles with. This had caused him to keep Annie at a distance by continuing to act in a "big brother" type role. Ultimately he recognized how harmful forcing this dynamic between them was when they both have non-fraternal feelings for each other ("Geography of Global Conflict"). Annie has subtlety implied she understands Jeff's reservations ("Horror Fiction in Seven Spooky Steps"), but she also has bitter feelings over his earlier denials about his feelings for her ("Digital Exploration of Interior Design"), ("Paradigms of Human Memory"). They respect each other and have acknowledged that they both care how the other sees them ("Intro to Political Science"). While inside the Dreamatorium, Annie is confronted by Abed role playing as an idealized version of her who is madly in love with Jeff. She rejects this version of herself but admits to having some selfish motivations in kissing Jeff outside the Tranny Dance ("Virtual Systems Analysis"). While she still is strongly attracted and will sometimes indulge in fantasies about being married to him ("Conventions of Space and Time") she understands that it hasn't become love yet. Jeff for his part may be becoming more enamored with her; this is shown when a look inside Jeff's heart reveals several pictures of Annie (as well as a few of her cleavage) ("Urban Matrimony and the Sandwich Arts"). It also further illustrated when he opens the door to the lab by generating an intense burst of passion after looking at Annie ("Basic Story").
Creator Dan Harmon has openly stated his appreciation of the fans dedicated to this pairing and mentioned in several interviews a particular fanvid he saw which made him aware of shippers. The Season One finale kiss was intended to be a nod to those fans, and later in Season Two, he made another gesture through a montage meant to pay homage to the shipper video. Several entertainment reporters have also acknowledged Jeff and Annie; most notably Micheal Ausiello from Entertainment Weekly is known to be a big fan. In 2011, Jeff and Annie were nominated for the E! Online 2011 Top TV Couple Award. By a very slim margin, they managed to overcome the more well-known TV pairing House and Cuddy and win the award. Joel McHale sent a somewhat tongue-in-cheek email to E! accepting the award:
"It's so great for Community's Annie and Jeff to win E! Online's poll for best couple. The fans for the show are incredible, and I thank you. I hate to point this out, but Jeff and Annie are not a couple."
An online fansite devoted to the pairing can be found on livejournal called "Milady/Milord.