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 openly 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 creates an underlying tension between them throughout the rest of their freshmen year at Greendale and culminates in another kiss outside the Tranny Dance. Jeff initially tries to keep his distance from Annie; he is uncomfortable with the age difference and denies to her several times that anything is going on between them. Recently, however, Jeff has become a bit more honest about his feelings. 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 who 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, return for an unexpected fifth year together at Greendale. Jeff has accepted a teaching position at school as the new Law professor. Annie enrolls on his vlast to make sure he is actually doing his job. The two later team up to try and catch the mysterious assailant known as the "Ass Crack Bandit". Their investigation is abandoned when they learn that Pierce Hawthorne has died. The two meet out with the study group to mourn the loss of their friend. A reading of his will reveals Troy stands to inherit Pierces share of Hawthorne Wipes on the condition he sail around the world. Jeff and Annie team up when Abed hosts a campus wide game of "Hot Lava" in honor of Troy's imminent departure.
At the start of the show, Jeff and Annie were meant to have a more fraternal dynamic between them although there were hints that Annie had a small crush on him; this can be seen in "Spanish 101" when they began their signature greeting to each other, "Milady/Milord". In "Football, Feminism and You", the age difference was established in order to reinforce the idea of the older brother/little sister relationship. 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. However, once it was discovered that the two had onscreen chemistry, they were paired together more afterwards. In this interview and on DVD commentaries, Dan Harmon mentions how he had decided to add a romantic element to the dynamic in order to gauge audience reaction. When the episode "Debate 109" made the attraction canon, the popularity of the pairing increased. They now have a long running sexual tension which has fueled most of their interactions on the show and enjoys a sizable following online (see Fandom below).
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, hinted to be 12 years, has been something that clearly bothers Jeff as evidenced by his reactions in "Anthropology 101" and "Asian Population Studies", although it has become less of an issue now that Annie is no longer a teenager. Jeff has admitted that he tried to keep Annie at a distance by treating her like a child but recognized how harmful it was to continue doing so when they both have feelings for each other. Annie has subtly shown that she fully understands Jeff's reservations ("Horror Fiction in Seven Spooky Steps)", but she also has bitter feelings over his earlier rejections of her ("Digital Exploration of Interior Design"). They respect each other and have acknowledged that they both care how the other sees them ("Intro To Political Science"). In "Virtual Systems Analysis", 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 selfish motivations in kissing Jeff outside the Tranny Dance, suggesting her attraction is partially based upon her desire not to be alone. This also may indicate that Annie's view of romance has matured and while she may be strongly attracted to Jeff ("Origins of Vampire Mythology") she understands that it hasn't become love yet. Jeff for his part may be becoming more enamored with her; this is shown in"Urban Matrimony and the Sandwich Arts" when a look inside Jeff's heart reveals several pictures of Annie (as well as a few of her cleavage).
In several interviews (, ), the creator of the show Dan Harmon mentioned his thoughts on how romantic relationships are handled on TV as well as how they would be developed on Community. While he praised shows that were able to execute the concept of a will-they-won't they pairing, he felt that audiences were tired of seeing that and wanted to approach it in a different way. He also wanted to make sure that no one pairing would overshadow the ensemble, and that the interactions of all of the main characters would be the most important relationship. To that end, he wanted to make every pairing a viable romantic prospect and would include shout outs to devotees of certain pairings who are known online as "shippers". Because of their popularity, Jeff and Annie has been teased the most out of all the possibilities. 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 the 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.