Community: How Many Women Jeff Winger Dated Across All 6 Seasons

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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.

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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