Since all of my stories about my favorite Greendale pairing are them either getting together and "living happily ever after" or them already together "living happily ever after", I wanted to do something where things weren't so easy for my favorite ship once they do actually become involved.
The first time they got together was November of their third year at Greendale. Jeff had driven Annie home after the group had watched Abed's latest film. Once they got to Dildopolos Jeff insisted on walking her to her apartment. As they stood in the hallway talking they unconsciously started inching their faces closer until their lips met. Kissing wasn't exactly new for them. They had already locked lips at the debate and at the Tranny dance (and although they hadn't Annie couldn't help feeling that they once made out at Abed and Troy's apartment.) But this time Annie insisted that something more come out of it. And shockingly Jeff agreed. They went out on a few dates to test their new relationship status before telling the group they were a couple. While not everyone was exactly supportive of the outcome no one was surprised by what they heard, with Abed stating, "this character development has been in the works for a while now." While at first things were good it wasn't relatively long before it started falling apart. Whenever they were in public Jeff was always self-conscious about showing affection towards Annie. This led to some heated fights between them. Annie stated that he still had a problem with her being younger then him while he tried to act like he just wasn't the type of guy who showered woman with cutesy affection. It finally collimated with Annie breaking up with Jeff three months after their romantic relationship started, stating that she couldn't be with someone who couldn't be with her fully. It was hard on both of them, but with support from their friends they were able to regain what they had before they became a couple, though understandably at a lesser degree then before.
The second time they got together was early March of their third year at Greendale. The group had gone out to a bar one night and after several hours of drinking games and darts people starting leaving one by one, until Jeff and Annie were the only ones left. They took a cab back to Jeff's place, with the original intention that Annie would sleep on Jeff's couch. Instead they ended up in bed together. This time they didn't tell the group they were involved again. And this time it was decided that they simply have sex without any qualms of a relationship developing. Even at their worst the sex had always been great. And for once Annie enjoyed being with someone purely for the sake of having sex. To her it felt grown up and something a sophisticated woman would do. Hell, Britta and Jeff did just that for months, so why couldn't she? But after a few weeks she started feeling restless and unsatisfied with their arrangement. And one night she finally confessed to Jeff that she wanted more. He replied that he was still the same guy he always was and if they were in a actual relationship they would just go through the same shit they dealt with before. So they decided they shouldn't sleep together anymore. That breakup was even harder then the first one had been, because this time Annie had sworn to herself that she wouldn't allow herself to get hurt and she had done just that. As she left Jeff's apartment she swore to herself that she would never again let him into her heart.
The third time they got together was over the summer before their fourth year at Greendale. Jeff had gone to get some ice cream one night and found that Annie had taken a job as an ice cream scooper for the summer. He bought her a cone and after her shift ended they decided to see a movie, which resulted in a furious two-hour make out session in the theater. This time they decided on a kind of middle ground to where they had ended up in their last two relationships. They agreed that this would just be a 'Summer Fling' and would go no further then the end of the summer. This time things worked out much better with them. It could have been the carefree nature of summer or knowing there would be an actual end, but this time it just worked. They went out to dinner, saw movies, went biking, laid on the grass at the park, had passionate sex, ate a lot of BBQ of various degrees of quality. Again they decided to keep their relationship a secret from the group. But this time the group heavily suspected that they were involved again (mostly due to their tendency to horse around in Pierce's pool during his frequent summer mansion gatherings.) At the end of August they ended things, not wanting to potentially ruin the great time they had had. But as they parted Annie was hurt that it had to end, and angry that Jeff could be so open and carefree on a temporary basis but not on a permanent one. And Jeff was angry with himself for allowing her to get away even though he know how awesome she was.
The fourth time they got together was November of their fourth year at Greendale, almost a year to the day of when they entered their first relationship. This time they tried to give it a go again at having a real relationship. They told the group and dated openly. And this time Jeff didn't have his previous hang-ups on showing affection to Annie in public. But things again weren't easy. Again Annie's age was a cause of concern for Jeff, but for reasons that were different then before. To his dismay Annie was acting more like a immature kid then usual. She spent a great deal of time with Troy and Abed participating in their unique adventures. She started showing up late to class and then skipping class. When Jeff confronted her about it she explained that soon she would be out of school and in the real world, and she wanted to have some fun before she lost that chance. He told her she was being stupid and that just because she wouldn't be in Greendale didn't mean she couldn't have fun. It came to a head one day when she rushed out to go play laser tag with Abed and Troy and forgot to mail off her grad school application. When she got back Jeff screamed at her that she was ruining everything she had worked for. She yelled back that she had just forgot and that he shouldn't be acting like her father. While she later admitted that she had been putting fun over her future that fight caused them to break up yet again.
The fifth time they got together was February of their fourth year at Greendale. This time when they told the group they were met with disbelief and concern. Everyone had their own two cents to put in on them being together again:
Shirley: "Why are you two doing this to yourselves again? You know it's just going to end in heartache."
Britta: "You know what Annie, I've had it. I'm not going to be there for you this time when you get your heart broken."
Troy: "Guys, even I can see that this is a bad idea."
Abed: "Even from a 'will they or won't they standpoint' this has gotten to the point where you two just aren't meant to be together."
Pierce: "Jeff, how good can the milk really be if you keep getting rid of the cow? Annie don't worry, I talking about the sex. Not your big jugs."
In all honesty they weren't exactly sure why it didn't work out this time. It might have been that the group was constantly waiting for the other shoe to drop. Or it might have been the fact that they were just tired of the heartache and the constant fight to make it work. Either way they were only together for a few weeks this time before they ended it. This time the breakup was mutual. And while it still hurt they felt better about it then all the other times they had ended things. When they graduated Greendale community college they were more or less friends, and agreed that while they didn't regret what they had it was better that they weren't together. They went off to live their lives, sure that they would never see each other again.
A year later they met again, in New York City of all places. After a year of working at his old law firm Jeff was offered and accepted a position at a prestigious firm in New York. A week after he arrived he ran into Annie, who herself had transferred to a school in New York. Both were shocked to see each other, neither having spoken to the other in a year. After the initial awkwardness they decided to meet for coffee to catch up. This led to hanging out and spending a great deal of time together. As they would walk together in Central Park or ice skate at Rockefeller Center Jeff could almost hear Abed quoting 'When Harry Met Sally' in his head. This time they didn't even try to analyze or put a label on what they were. This continued when they started sleeping together, and were only involved with each other, and moved in together, and would go out on what most people would accurately describe as dates. In fact, the only time they did put a label on their relationship was four years after they met up in New York, when they would call each other husband and wife.
Whenever anyone asked them why it took so many tries for them to make it work or why they kept going back to each other in spite of all the heartache, neither had a clear answer to the question. It was something they couldn't even describe to the group. In the end they would simply say that somehow they knew they were meant to be together. They just kept getting the start time wrong.