Jeffery Winger
Britta Perry
Jeff and Britta have one of the most chaotic yet oddly functional relationships in Community. At the start, it’s a classic “will-they-won’t-they” dynamic, with Jeff initially pursuing Britta as more of a conquest, while she sees right through his nonsense but still finds him intriguing. As the show progresses, they develop a love-hate, bickering, almost sibling-like relationship. They hook up multiple times but ultimately realize they’re better off as friends (or frenemies). They both have egos, enjoy messing with each other, and act like they’re too cool for deep emotions—though Britta, ironically, is the more emotionally driven one despite trying to act rational and detached.
Annie Edison
Jeff and Annie have one of the most complicated and debated relationships in Community. From the start, there’s undeniable chemistry between them—Annie is idealistic, ambitious, and a bit naïve, while Jeff is jaded, sarcastic, and emotionally guarded. Their dynamic is built on a mix of flirtation, mutual admiration, and ethical dilemmas (mostly on Jeff’s end, considering the age gap). At first, Annie clearly has a crush on Jeff, and while he resists it, he can’t help but be drawn to her. Over time, it becomes more of a two-way street, with Jeff showing moments of vulnerability around Annie that he doesn’t often show with others.
Abed Nadir
Jeff and Abed have one of the most underrated relationships in Community. At first, Jeff finds Abed weird and hard to relate to, while Abed sees Jeff as the stereotypical protagonist of a TV show—someone who fits the mold of a classic leading man. Over time, though, their dynamic becomes a mix of reluctant respect, occasional frustration, and unexpected emotional depth. Jeff often plays the “straight man” to Abed’s eccentric, meta-obsessed behavior, but there are moments where he genuinely connects with him. At the same time, Jeff struggles with Abed’s tendency to blur fiction and reality. He gets frustrated with Abed’s antics—like when Abed turns their group into a Doctor Who-style show (Inspector Spacetime) or forces Jeff to admit he likes spending time with them all in the Pulp Fiction episode. But deep down, Jeff respects Abed’s unique way of seeing the world. hours.
Troy Barnes
Jeff and Troy have a funny, evolving dynamic that starts off with Jeff treating Troy like an immature kid and eventually grows into a genuine, if not always obvious, friendship. Early on, Jeff sees Troy as just the stereotypical jock—a dumb but confident high school quarterback. Meanwhile, Troy sees Jeff as the cool older guy and occasionally tries to impress him. But as Troy starts to break out of his jock persona and embrace his goofier side (thanks to Abed), Jeff begins to respect him more. By the middle seasons, their relationship becomes more of a “big brother/little brother” thing. Jeff still teases Troy, but he also gives him advice (sometimes terrible advice) and steps up to support him when needed.
Shirley Bennet
Jeff and Shirley have a really interesting and sometimes overlooked dynamic in Community. On the surface, they seem like total opposites—Jeff is a self-centered, too-cool-for-everything ex-lawyer, while Shirley is a sweet but passive-aggressive Christian mom. However, their relationship is built on mutual respect, occasional conflict, and a surprising amount of shared pettiness. At first, Jeff doesn’t take Shirley seriously. He often dismisses her as just the “mom” of the group, and Shirley sees him as an arrogant, selfish playboy. But as the show progresses, they start to see each other’s complexities. Jeff acknowledges that Shirley is much tougher and savvier than he initially thought, and Shirley realizes that Jeff, despite his attitude, does care about people in his own way.
Piercenald Hawthorne
Jeff and Pierce have one of the most complicated and, at times, toxic relationships in Community. From the very beginning, Jeff sees Pierce as an embarrassing, out-of-touch old man, while Pierce sees Jeff as a younger version of himself—someone he both admires and resents. Jeff constantly insults Pierce, dismisses him, and often tries to distance himself from him. However, there are moments where Jeff actually feels sorry for Pierce, recognizing that beneath all the offensive jokes and desperate attempts for attention, Pierce is just a lonely guy who doesn’t know how to connect with people. Despite this, Jeff never fully trusts Pierce, because Pierce has a habit of being manipulative and spiteful—especially when he feels left out. Ultimately, their relationship is one of reluctant tolerance. Jeff never fully forgives Pierce for his worst moments, and Pierce sees Jeff as both a rival and a surrogate son he can never truly win over.
