This story jumps around a little bit, but the dates are there, so hopefully it won't be too confusing! Thank you so much in advance for reading! :)

Also, as a disclaimer, if I owned Community, I wouldn't need to write fanfiction to get Jeff and Annie together sooner!

2015

Tugging on the black bowtie he had just put on, Jeff grinned at his reflection in the mirror. The reason he was wearing a bowtie instead of his usual skinny tie was the same reason he was wearing a tuxedo instead of one of his usual suits. It was the same reason that he was the most terrified that he had ever been in his entire life, yet oddly calm at the same time. After years of avoiding commitment of any kind, he was about to make the biggest promise of his life. He heard a soft knock on the door, and opened it to see Troy and Abed, two of his groomsmen, beaming up at him.

"Are you ready?" asked Troy.

Jeff laughed at his question. He was more ready now than he had ever been, which made him feel even more at ease with the decision he made.

2012

"Shirley, I'm not going to be able to attend your son's birthday party this weekend, because my cousin's getting married. Thank you for inviting me, though," Annie explained with trepidation. She hated disappointing people more than anything, and Shirley was one of the easiest people to disappoint.

Jeff scoffed in disgust, never taking his eyes away from the game of Bejeweled on his phone, "Why would anyone willingly commit themselves to one person for the rest of their life when the odds say that it's probably not going to work out anyway?"

"I didn't ask you to marry me, Jeff. I just said I was attending a wedding. Save your anti-establishment opinions for someone who wants to hear them."

Troy's eyes widened, "Annie!"

"Why have you two been so crabby lately?" inquired Britta.

"I have not been crabby. I'm just irritated that Jeff insists on having a negative attitude towards everything."

"Because having a negative attitude toward me is going to fix that," retorted Jeff.

The rest of the study group made uncomfortable glances at one another while Jeff and Annie glared at each other and Abed pantomimed slicing a sword through the air.

"Cutting the tension with a knife," Abed explained, when nobody asked. "I feel like this situation is a little tired and played out. It's will they, won't they, almost to the point of Ross and Rachel, although I feel like I'm missing out on a piece of interaction. Did anything happen to you two before or during break? Did it have something to do with the glee club episode?"

"Abed," Jeff grunted through his teeth, "for the last time, this is reality. We aren't living in a television show.

"Abed's right, though. You both were fine before break, and as soon as this semester began you've been at each other's throats. Annie, how exactly did you pull Jeff over to the dark side that is glee club?" Britta questioned.

Conveniently, the bell rang, and both Jeff and Annie took the opportunity to dart out of the room before they could be bombarded with any more questions. Annie didn't want to have to explain what kind of song she sang to Jeff, and especially not what she was wearing or the effect that she was trying to have on him.

As they left the study room and headed for the cafeteria, Jeff pulled Annie aside into an empty classroom, "Look you could tone down-"

"Oh, is it my fault again? I'm the one who has the problem with discretion, I'm the one who's too young, and I'm the one who doesn't understand why you spend your nights with arbitrary women instead of admitting that you want to be in a relationship with me!"

Annie's eyes were manic and hurt, and Jeff felt like she had just punched him in the stomach.

"No, Annie. It's my fault. I'm the one who kissed you back, I'm the one who leads you on, and I'm the creepy old guy who keeps denying that I want to be in a relationship with you."

Her eyes softened the slightest bit, but she didn't want to let her guard down completely. She had been in too many situations with Jeff to know that a single heart-to-heart with him didn't mean that they would walk out of the room in a relationship.

"First of all, you're not creepy, and you're not old, and I'm not that young. You're not allowed to use that an excuse anymore. Second of all, I know that you haven't necessarily been a fan of relationships in the past, but you can't keep refusing your attraction to me while sabotaging any chance I have at a relationship with someone else. Relationships aren't that complicated. You can either give it a try or you can let me move on."

Jeff sighed. If he were Abed, he wouldn't be sure if what he was about to say gelled with his character development so far, but then again, he was not the same person he was on the first day he walked through the doors of Greendale Community College. "You're right. I'm not being fair, but even though I'm scared, a big part of me never wants you to move on. I don't want you to get over me, because I don't think I'd be able to get over you."

She stared, dumbstruck, at him before she could finally manage to say, "Are you telling me that you're committing to a relationship with me?"

He looked at her earnestly, "That's exactly what I'm saying."

Annie beamed from ear to ear and leaned forward to kiss Jeff and whisper into his ear, "Now we just have to break it to the group."

"Oh, I think that part's already taken care of," spoke a surprisingly judgmental voice. Annie and Jeff broke away and realized that the study group had been standing right outside the doorframe.

"How much of that did you hear?" Annie asked as her face flushed.

"Not so much hearing anything as seeing you two locking lips," replied an agitated Troy.

"Well, in that case, you missed the most important part. Annie and I feel very strongly for each other, and we have for quite a while. Neither of us wants to cause a rift in the group, but denying our feelings for each other had almost done that. Frankly, I'm a little disappointed in you all. If you think that our relationship would be detrimental to the group, even to the point of breaking it up, then maybe we're not all as close as I thought we were. This group has gone through so many-"

"He's making a speech of nonsense to make it look like we're the ones who did something wrong!" Britta accused.

"Well, Jeff and I didn't do anything wrong either! Our only crime is having feelings for each other," countered Annie. "This has the potential to be a really good thing, if you guys will just let it happen."

"I'm not really surprised," interjected Abed. "Being as perspicacious as I am, it has become quite clear that you two have become much closer. To be honest, I was astonished that you hadn't gotten together sooner. I thought it would be a great season opener, but I guess it also works well as a mid-season plot twist."

When everyone agreed to listen to reason, they gave Jeff and Annie their blessings on the condition that Jeff wouldn't take advantage of her youth and Annie wouldn't let Jeff take advantage of her youth. Annie brushed off the fact that the group still perceived her as naïve and Jeff brushed off the fact that the group perceived him as a little creepy. They didn't care about that, because after all of the warnings, they were finally accepted as a couple. Smiling to himself, Jeff realized that these were the only people in the world that he would go to such lengths to appease.

2014

Jeff hated shows of grandeur. He hated big romantic gestures. It's what made him different from Rich. Rich was the guy that would rent a blimp to ask a girl out on a first date. Jeff wouldn't do that. He would buy a bottle of champagne and cook a fancy meal, but he wouldn't rent a blimp. Thinking of all the ways he wouldn't propose to Annie, he ruled out too many ways that he could propose to her. He didn't want it to be cliché, but he still wanted it to be romantic. Maybe cheesiness was inescapable when it came to proposals. Annie was special to him and he wanted his proposal to be special to her. It took him three months after he bought the ring to figure out exactly how he would propose.

Turning off the engine of his Lexus, he was completely satisfied with the choice he made. He led Annie out of the car and through the Greendale parking lot. The sky was black, but the shrubbery around the entrance to the building was lit up with strings of lights. Jeff had driven Annie to their Alma Matter on the pretense that the Dean had some sort of proposition for her. If she hadn't been too wrapped up in her new job, she might have noticed something amiss with Jeff's excuse, but she was busy and stressed, so she humored him. They were to stop by Greendale on their way to dinner, so Annie dressed up in her favorite black dress and Jeff wore one of his favorite suits. He stopped her just short of the entrance to the school.

"Do you remember what happened here at the end of our first year here?"

Annie smiled. She remembered it fondly. She and Jeff kissed on that very spot after the Transfer Dance. Knowing that Jeff knew that she remembered, she simply squeezed his hand and buried her face in his arm. His heart rate doubled as he started forward again. He led her through the hallway, which had also been lit only with string lights, all the way to group study room F. Annie, catching on halfway through the hall, audibly gasped as she saw the entire room was covered with a profligacy of rose petals. She knew the extravagant gesture was killing Jeff silently, as he preferred to be subtler when it came to actually being in a relationship instead of just trying to sleep with someone. She knew he didn't know how he even felt about relationships, and this was huge for him. Tears of happiness flooded out as she looked up at him.

"Annie Edison, you know I love you very much."

"I love you too," she could barely get out through her emotions.

"I know, and I wake up every day so thankful that you do. You are the most wonderful person I have ever met. And this is where we met, right here at this table. I have learned so much from you, and you have made me a better person. I like to think that you have made me into someone that deserves to be with you. You're a strong, determined, beautiful woman. You make me happier than I ever thought I could be, and I never want to live without you," he knelt down on one knee and pulled out a tiny box from his pocket as Annie's hands involuntarily flew up to cover her mouth. "Annie Edison, will you marry me?"

Flinging her arms around him and joining her lips with his, she broke away just long enough to say, "Jeff Winger, I can't think of anything else I would rather do than spend the rest of my life with you."

She wished she had just said yes, instead of making the moment even cheesier for him, but he couldn't have cared less. The only thing that mattered was that she agreed to marry him.

2015

Britta was the first person Annie called about the engagement. Annie asked her if she would be the maid of honor, and then asked Shirley if she would be a bridesmaid. Jeff had surprisingly chosen Abed as his best man, due to the fact that out of all the men in the study group, Jeff had the fondest memories from hanging out with Abed. Of course, he also made Troy a groomsman, as well as Pierce. Annie focused her driven personality into planning the perfect wedding, and it paid off. The ceremony was to take place in a beautiful bed and breakfast in Denver. They didn't need a lot of space for guests, because it was a textbook definition "small wedding". Only the study group, a few friends from school and work, and some family members were to attend.

Annie took one last look at the room she was going to be married in. String lights hung across the ceiling and cream-colored roses covered any vacant space. She thought about how striking the emerald green bridesmaid dresses would look against the décor.

All of the months of planning had paid off and hers was going to be the most beautiful wedding she'd ever attended. She was a little biased, however, because in her eyes, the most beautiful thing about her wedding was the groom. Tomorrow, she would be Jeff's wife, and she thanked her lucky stars that they met, six years ago in group study room F.

Getting ready for the ceremony, Jeff tugged on his bowtie. He was uncharacteristically nervous, although at the same time he was certain that Annie loved him as much as he loved her. He took deep breaths to steady himself and flashed a winning smile at his reflection. A knock on the door made him aware that his best man was waiting outside the room for him to finish getting dressed. Abed and Troy entered, asking either if he was ready in his tux or ready to make the biggest commitment of his life. Jeff wasn't sure which question they were asking, but he was clearly dressed and he was clearly in the mindset to exchange vows with Annie, so he chuckled and responded that yes, he was ready.

Jeff got even more excited when he saw the room where the ceremony was to take place. Annie had really outdone herself. He couldn't imagine getting married in a room that was more beautiful than this. As the ceremony began, he watched his friends traipse down the short aisle and gather on either side of him. After what seemed like entirely too long of a wait, he caught a glimpse of Annie's white dress in the doorway. She peeked out and once her eyes found his, her nervous expression melted into one of affection. He tried to savor every moment she spent making her way down the aisle, taking in every ounce of her splendor. As she seemed to float toward him in her ethereal gown, Jeff was pretty sure that this was the closest that anyone had ever gotten to marrying an angel.

They exchanged vows, and Jeff knew from his first sentence that getting Annie to abstain from tears was a lost cause. He hated seeing her crying, but he didn't mind as much when he was sure that the tears were caused only by happiness. Annie, on the other hand, failed to make Jeff cry, even though she put as many tear-jerking moments into her speech as she could. She did succeed in making Troy and Shirley openly weep, however. The night went on without a single hitch, besides Abed catching Troy and Britta making out in the garden outside, and finding out that they had been carrying on a secret relationship for months. All in all, Jeff and Annie could not have asked for a more picturesque wedding. Jeff smiled at the irony that after being afraid to commit to anything in his life, marrying Annie was the best decision he made and would ever make.

2011

Jeff stared down the bottle of scotch on his coffee table. He wasn't drunk yet, but he knew that if he wanted to stop thinking about the events that took place at the end of the semester, he would have to drink copious amounts of alcohol to drown out the dirty thoughts swimming around his head. He wasn't sure where Annie learned how to dress or act like that – well, yes, he did. She used to live above freakin' Dildopolis. She was an adult who lived above an adult store. Of course she wasn't naïve anymore. That didn't erase the fact that she was much younger than him and he couldn't stop thinking about her no matter how much booze he drank. A pounding on his door interrupted his staring contest with the bottle. As if summoned by his thoughts, Annie stood, waiting outside his doorway. He barely cracked open the door when she barreled through into his apartment.

"We need to talk," she began. "I was just going to let it go unresolved through winter break, but, let's face it, have I ever been able to let things go that easily?"

Jeff let out a dry laugh and raised his eyebrows, "You've never been known to let things stay unresolved."

"Yes, well, obviously you're aware that I did something that I'm not entirely proud of at the end of the semester."

"You're referring to the sexy Mrs. Clause routine?"

"It wasn't sexy. Well…I mean, I tried, but even you said it lost its appeal halfway through."

"Annie, that's because you shouldn't dumb yourself down for sex appeal."
"I know that! I was just deluded at the time! I don't know what I was thinking."

"Well, you don't have to worry. I'm not going to tell anyone about it. If you regret the seduction – "

"I don't regret that! I regret the way it happened. I should have known that if I wanted you to start seeing me as an adult I should have taken a different approach."

Jeff's face fell. This is what he was worried about. He did see her as an adult. She was a smart, strong, wonderful woman who deserved to have his emotional ineptness and inability to be in a stable relationship as far away as possible from her love life. "Annie, we've talked about this. You know I care about you, but I can't give you any more than that."

"Because relationships are complicated? Jeff, you really are ridiculous. You're afraid of commitment. You've never committed to anything in your life, and you don't know how to start. I'm not stupid. I see the way you watch me when we're studying and you think no one is looking. You get jealous when I even mention another guy to the group, no matter what the context is. I've asked you before, and I guess I need to ask you again. What are you choosing? Because if you're not going to let this progress, you need to let me go."

"I don't know what to tell you! I'm not ready! You can't just come to my apartment and blindside me with these questions."

"As if you weren't already thinking about it?" She lets out a frustrated shout. "I can't do this anymore. I'm going home."

"I thought you didn't want to leave this unresolved," Jeff raised his voice to match hers.

"Well, it's unresolved and I'm leaving!" Annie slammed the door on her way out.

Shit. Jeff closed his eyes and sank down to the carpet against the door. Every day that went by, the line that defined their relationship blurred more and more, and he wasn't sure there even was a line anymore, but instead, a tangled mess of confusing confessions and denials. He knew she would be furious with him for the remainder of break, no matter what he did, so he resolved to give her space until classes resumed. That would give him all the more time to work on his own problems, and maybe by the time they spoke again, he would be able to take a baby step into making promises that he would be able to keep. There was no way that he would ever be able to let her go, so the only thing that he could do was try harder for her. He needed to make himself a better man. Jeff clenched his jaw and shook his head as he realized that only for Annie would he go to such lengths to appease.

2015

Annie sighed into Jeff's chest, and he tightened his grip around her as they danced their first dance as a married couple. Married. They made a promise to each other that they would stay together forever, and Jeff wasn't the slightest bit worried that he would ever even consider breaking that promise.