Jeff Winger is known for being a bit of a ladies man — or at least in his head. We all know that he started the OG study group just to try to get with Britta, but instead, he set up six years of glorious television — more or yes, depending on how you feel about the "gas leak year".
Despite having a number of women interested in him throughout the series, Jeff had a rather strange ending for a handsome leading man on a sitcom. Who did Jeff end up with on Community? No one. Well, sort of.
Did Jeff end up with Britta or Annie at the end of 'Community'?
Throughout the series, Jeff (Joel McHale), Annie (Alison Brie), and Britta (Gillian Jacobs) were in a somewhat love triangle. When Jeff initially started the study group, or rather lied about having a study group, it was to get Britta to spend time with him because, well, he wanted to get in her pants. Instead, he got a real study group that, more or less, lasted through six seasons (and a movie?).
But upon creating the study group, Jeff met Annie. At the time, Jeff was 34. Annie was 18 and she had a bit of a school girl crush on him. Which, over time, Jeff became pretty into, something he found kind of gross about himself. But that didn't stop them from sharing multiple kisses over the years.
On the other hand, Britta and Jeff never really had the romance that Annie and Jeff did. Their relationship was always a heated, sexual one. Although Britta once professed her love and they almost got married another time, they came to realize that, when they fell back to feeling attracted to each other romantically, there was always an outside force acting on it, like alcohol and jealousy. They did experience several hookups over the seasons, mainly in Season 2, but they worked better as partners-in-crime rather than romantic partners.
In the 'Community' finale, Jeff imagined a world where he was married to Annie.
The series finale of Community showed a struggling Jeff, who couldn't come to terms with the fact that his family was going off in different places. Though he graduated before his friends, he became a teacher at Greendale, effectively meaning that he never left the community college.
On the other hand, his friends did. He had already seen Shirley (Yvette Nicole Brown) and Troy (Donald Glover) leave and Pierce (Chevy Chase) die. Britta left the school and became a bartender. But Abed (Danny Pudi) and Annie's fates were left uncertain.
But after year 6 at Greendale, as everyone else planned out next "season", Jeff shut them down, saying it's not a show and he just wanted it all to be over and done with. It was summer and he was done with Greendale. That is, until Annie admitted that she was leaving to go intern with the FBI.
It's Annie leaving that scared Jeff the most. When Britta said that she's taking Annie's room if she doesn't come back, she replied, "Well, I'm definitely coming back. Probably. Maybe."
This prompted Jeff to come up with scenarios for "Season 7". In one, Annie commuted from Greendale to the internship in D.C., though she asked why the audience wouldn't feel bad for her in that situation since that's a lot of pressure for her to have to essentially live a life in both places.
In another, all of the study group were working at Greendale as staff members and Annie was the criminology professor, but she was also the "original Annie." Essentially, Jeff made her 18 again in his mind, or at least act and dress how she did before she started to grow and change.
In the final scenario, original Annie was back again, but this time, she was Jeff's wife and the mother of his child.
"Is this really what you want?" fantasy Annie asked.
"Of course," Jeff replied. "I'd be fine with a dog, too. But whatever you want."
"Do you have any idea what I want?" she asked.
Here inlies the problem of the Jeff and Annie relationship. Jeff knew what he wanted. But he had to let Annie go figure out what she wanted. In the end, Jeff and real Annie said a final goodbye, with him saying that he's letting her go and them sharing a last kiss. In the end, Annie leaves and Jeff joins Britta and the remaining crew at the bar she works at.
In the end, Jeff ends up alone. And creator Dan Harmon says that's what had to happen.
In an interview with TV Insider, the show's creator, Dan Harmon, admitted that he didn't think it was right that Annie and Jeff end up together. And it wasn't about their age. It was about their life experiences.
"Do we really believe in our heart of hearts that the current version of Jeff Winger and the current version of Annie Edison would be happily ever after if they ever got together? Or is it more likely their souls are intermingled and there is such a thing as true love that is genuinely star crossed?" he said. "This person hasn't lived their life yet. I'm comfortable with the realization that he's genuinely in love with her, but that's a separate thing from whether that's actually good for her."