Community's Jeff Winger has a reputation as a womanizer, but how many women does he actually date over the course of Community's 6 seasons? Played by Joel McHale, Jeff was initially introduced as a cynical ex-lawyer who casually dated and discarded women, before eventually softening. However, in comparison with some other sitcom characters, Jeff doesn't really have that many on-screen relationships.
Community developed a fervent fan following over its 6 season run, and fans often speculated about which relationships characters would end up in. This was especially true for Jeff, who had romantic tension and interactions with both Gillian Jacobs' Britta and Alison Brie's Annie. However, for most of the series, Jeff maintained a friendly relationship with both while occasionally pursuing women outside of the group. Jeff's romantic pursuits often led to tension among the group, especially in the early seasons of Community.
Many Community episodes featured one-off characters like Jeff's brother Willy Jr., including some love interests for Jeff. In Community season 1, episode 11 "The Politics of Human Sexuality," Jeff goes on a date with Dean Pelton's assistant Sabrina Shmuckle, but ultimately loses interest in her because of her immaturity. Jeff also has a brief fling with Pierce's step-daughter Amber, but breaks things off with her after learning she is scamming Pierce. However, these are really the only two examples of Community doing a "date of the week" storyline of the type common on other comedies like Seinfeld or Sex and the City. Taken together with the three more serious relationships over the course of the series, in Community Jeff only dates five women across the 6 seasons, meaning that Jeff's womanizing reputation is established more through offhand dialogue and casual acquaintances rather than more established relationships.
Who Did Jeff Winger End Up With At The End Of Community
While Jeff and Annie kiss in Community season 1, episode 0 "Debate 109," and Jeff flirts with Britta from the very first Community episode, his first sustained romantic relationship in the show is with his Statistics professor Michelle Slater, who he begins dating in secret. Their relationship eventually becomes exposed, leading to a love triangle storyline with Britta. Both declare their love for him at a school dance, but Jeff is unable to make a choice, and quietly slips out of the dance. Slater isn't seen again after season 1, and the disappearance of the character is referenced in jokes in future seasons.
It is later revealed that Jeff began a friends-with-benefits relationship with Britta during the events of Community season 1, episode 23 "Modern Warfare," which they kept secret from the other members of the study group. After it is revealed, Jeff and Britta decide to stop the relationship. Over the following season, they have a number of flirtatious interactions, including drunkenly trying to get married at Shirley's wedding rehearsal, but never really become a formal couple.
The woman that Jeff comes closest to "ending up with" is Annie, but once again Community doesn't provide a conventional romantic resolution. Jeff and Annie maintain a simmering sexual tension over the course of the series, despite Jeff being uncomfortable with the age difference between them. In the Community series finale, Jeff and Annie admit their feelings for each other and kiss, but are separated by graduation and ultimately don't pursue a relationship. There are some hints that they could still get together in the long-gestating Community movie, but for the time being it seems that none of Jeff's relationships ended in a happily ever after.