Community went against sitcom conventions by not having any of the main characters end the show as a couple.
This was particularly surprising because Jeff Winger was involved in two will-they-or-won’t-they relationships throughout the series. The slick former lawyer had a thing for both Britta Perry and Annie Edison at different points during the six seasons. However, despite sharing many romantic moments with both of them, he never actually entered a serious long term relationship with either woman. Both Britta and Annie had great chemistry with Jeff, and a serious relationship with either of them had the potential to be amazing. But who was better suited for him?
Britta: Age-Appropriate
The age-gap between Jeff and Annie has been well-documented and was one of the sticking points of the two being a couple. It was not so bad in the later years when Annie was in her twenties, but when she first met Jeff, she was 18, and he was 34/35.
This age difference meant that every romantic interaction the pair shared in the early years of them knowing each other had an air of creepiness to it. Britta, on the other hand, was only six years younger than Winger, so the two of them being together was fine.
Annie: Good Beginnings
Jeff's romance with Britta had a superficial and dishonest start. The former lawyer saw her as "the hot girl from Spanish class," and attempted to woo her by creating a fake study group so they could spend some time together.
With Annie, Jeff met her in what was supposed to be the fake group. The pair didn't have much one on one interaction at first; their only connection was that they both took Spanish. However, once they started to speak more, it was clear they had chemistry, and sparks started to fly.
Britta: Similar Personalities
Before she became an airhead, Britta and Jeff were very similar people. They were both sarcastic, cynical, and vain. Sometimes people with similar personalities can struggle to coexist, but that wasn't the case with these two.
Many times the duo seemed more connected to each other than the rest of the group - Annie included - because they were so alike. Of course, the two still clashed a lot. Yet, their similarities added to their relationship more than it detracted from it.
Annie: Lack Of Bickering
Virtually all of the arguments Jeff and Annie ever had stemmed from her wanting him to do the right thing. They didn't argue about petty little things constantly or drive each other crazy with their need to get the last word.
The same can't be said for Jeff and Britta, who struggled to go ten minutes in each other's company without bickering. For example, when they spent all night fighting about which of their preferred bars was the best only to realize they were talking about the same one.
Britta: Helped Him With His Father
Many of Winger's flaws as a person came from his father abandoning him as a child. Understanding this, Britta tried to encourage him to meet with his dad on a few occasions, yet he always refused. Eventually, though, Jeff ed his father and organized a Thanksgiving dinner with him.
However, on the day, Jeff couldn't make it into the door. That is until he got a call from Britta, who revealed that she was at his dad's place, so he had to go back. Later in the night, Jeff finally confronted his dad and let him know what he did to him. Without Britta, he might've never gotten that closure.
Annie: Shared Sweet Moments
Jeff was never known for being the sweetest of people. Yet, on the occasions he did show his softer side, he was usually with Annie. From their cute "M'Lady" and "M'Lord" interactions to their ittance that they both care what the other thinks about them, the two of them have shared plenty of sweet moments together.
Britta never brought out this sweeter side of Winger, which could prove that he never cared about her as much as Annie.
Britta: Open About Their Feelings For Each Other
It didn’t take long after they first met for Jeff to ask Britta out on a date or make his feelings known that he wanted to sleep with her. While at the end of their first year at Greendale, Britta publicly declared that she loved him, albeit she later took it back. Then the two engaged in a secret physical relationship throughout their second year at the college.
Jeff and Britta rarely hid or repressed their feelings for each other. Winger’s interactions with Annie was completely different as the pair constantly skated around how they felt, even when it was obvious to onlookers that they liked one another.
Annie: Brought Out The Best In Him
Jeff was always a charming and likable guy, but he had his flaws. He was lazy, dishonest, and very self-centered, especially in his early days at Greendale. However, Annie commonly pushed him to do the right thing. For instance, it was her influence that convinced him to take his teaching job seriously.
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His relationship with Britta wasn't always as beneficial. Often, she was just as selfish and deceitful as him. He did some good things in an attempt to get Britta to sleep with him, yet that's hardly the same thing.
Britta: In A Similar Place In Life
By the end of the series, Jeff was a teacher at Greendale, and Britta was working at a bar nearby. They both were pretty content with where they were at, and neither of them seemed to have big plans to do anything else. The pair were settled, and if they started dating again, it was unlikely that life would've gotten in the way.
In contrast, Annie left for an internship at the F.B.I. She still had a lot to do and see in her life, and she wasn't ready to settle down with Jeff.
Annie: Romantic Feelings Never Faded
The former lawyer might’ve been romantically interested in Britta first, but he was into Annie for longer. While Britta and Jeff’s romantic feelings for one another were strong for two years, they then became good friends whose relationship rarely turned amorous.
However, as soon as Jeff thought of Annie as a potential lover, he couldn’t stop as much as he tried. And Annie’s infatuation with him started in their second year at Greendale, and those feelings remained just under the surface for the rest of her tenure at college.