Work Header

Someday or Sooner

Chapter Text

He woke up after having that dream again. The one where he was the one sailing around the world with LeVar Burton instead of Troy. Every dream ended with Jeff returning back to Greendale to find everything changed. Abed was still in LA, only Troy went with him. Britta was married to Starburns (he really needed to apologize to Dream Britta for that one), Pierce was still dead, but Shirley was back. The only problem was that Annie is never there when he returns. He spends the rest of his dream trying to find her, but wakes up before he ever gets anywhere.

Jeff’s had that dream too many times to count over the past summer, and the worst part was that he knew he was having them because Annie wasn’t meant to stay in Greendale. She was supposed to leave so she could find herself. He didn’t need a psychologist to figure out that his repetitive dreaming was Jeff telling himself he was feeling guilty and anxious about his and Annie’s future. Because yes, they were together. It was made official during the week after that night in the study room. Every day (and night) leading up to Annie’s internship was spent figuring out what they meant to each other.

After a few more honest moments and words (and kissing, lots and lots of kissing), Jeff and Annie decided that their relationship didn’t have to be put on hold until she got back. Sure, it would be extremely difficult and they would miss each other like crazy, but it would be worth it in the end. And if they were being honest, they had already been missing each other for a while. Ever since they all returned to Greendale, it hadn’t been the same.

But just because they were trying this whole relationship thing out didn’t mean that Jeff wasn’t worried he was holding her back. They had no idea what Annie’s future would be when she returned from her internship but she had a few more credits to complete, so she would be in Greendale for at least another year. They owed it to each other and themselves to finally be together.

“Annie, I can’t help but think that if you come back here, you will be missing out on your whole future. I can’t do that to you. I’m not worth it.” He remembered telling her those exact words on his couch days before she left.

“Jeff! Do you hear yourself right now? I want to be with you, why can’t you understand that?”

“Because! The variables! You said it yourself. There are too many. How can we do this if you have so much of your life in front of you.”

“Screw the variables, Jeff! I said that because we were interrupted and everyone was in the room. I know you want to be with me and I’m tired to waiting. Aren’t you tired?”

“Of course, I am! Dammit, Annie, I love you! Do you know how hard it’s been hiding that? Every day I see you and I can’t do anything about it. I’m too old, you’re a student, I have nothing to offer, you have your life ahead of you. The list goes on.”

“Well you’re gonna have to do something about it because I love you too!”

He had to admit, after that night, things felt easier. It was known that they loved each other and it was one step closer to finally being fine. It was also after that night that they slept together (in all connotations of the word). “You know this will make it harder to be away from each other now,” he told her as she pulled off his shirt. She wordlessly found a way to convince him that it would be worth it.

Jeff sat in bed and reflected on the fact that he was indeed correct. Having sex with Annie for four days straight made it unbearable to keep his hands off her all summer. But he smirked when he thought back on all the ways they made up for it. Just because they were over 1000 miles apart didn’t mean they couldn’t get creative with their phone calls and skype sessions…

But he was brought back to the present when his reminder popped up on his phone screen: PICK ANNIE UP FROM AIRPORT @ 4:00

His heart pounded at the thought of seeing her, of touching her, of being with her finally. He was undoubtedly excited, but it also meant that he would be in an honest to god relationship for the first time in years. But he didn’t have time to worry about it in the moment because he had to get ready.


He got there two hours early because he was anxious. He couldn’t sit around at home and wait for the hours to roll bye. He went to the gym, cleaned his apartment, and still had spare time before her flight landed. But now the hour was finally approaching and he brought himself to the waiting area. He was surrounded by other people waiting for friends and family, many of them had gifts and presents. A few of them had welcome home signs, and he was ashamed to admit that he was one of them. Earlier in the week he was scrolling through Facebook and saw that the Dean shared some corny, tear-jerking video of people returning home after being away. Of course, Jeff rolled his eyes (and struggled to not shed a tear at the part when a mother reunited with her son after her tour in Afghanistan) but he knew Annie loved that type of stuff. So two days ago he went to her apartment and used her stash of puffy paint to make a sign. Britta gave him absolute hell for it, but boyfriends did embarrassing things for their girlfriends right?

Which was why he found himself standing in front of the departure terminal with a small poster board with “Annie” written in purple block letters across the front. He added a few smiley faces and hearts for good measure (god, he was so lame).

But when he saw the passengers make their way, he didn’t care if he looked like a protagonist in some overrated romantic comedy. He held up his damn sign and waited for Annie to come into view with her polka-dot luggage and her warm smile. And sure enough, when she appeared wearing the t-shirt he gave her before she left in June, and rolling her suitcase like she held the world on his shoulders, Jeff’s entire world seemed to stop. He held his breath as she looked around for his face, and it was only when her eyes landed on him and she gave him the biggest smile that he was able to let air back into his lungs.

She saw his home-made sign and seemed to have melted, holding a hand over her chest and smiling adoringly as she approached. He gave her a crooked smile that seemed to grow as she stepped closer. When she stopped in front of him, it took everything in his power not to topple over her into a bone crushing embrace.

“Welcome home,” he said, still smiling.

“Jeff Winger,” she shook her head. “You must have really missed me,” she nodded towards the sign which he was still holding in front of him.

“You have no idea,” he inched closer.

“You’re such a dork, but you’re my dork and I love you.” She beamed at him.

Jeff chuckled and tossed the sign aside and pulled her into his arms. He held her and breathed in her scent, finding it hard to believe that she was away for ten weeks but now finally in his arms. “I love you. I’m so glad you’re home.”

“I am too. I missed you so much,” she squeezed his middle.

They pulled apart after a full minute of holding each other and Jeff tugged the hem of her t-shirt and smirked at her, “This is a nice shirt you’ve got here. Where did y--”

“Oh, just shut up and kiss me.”

He did.

It was tender and sweet but as he opened his mouth over hers, he attempted to make up for all of the hours and days and weeks they were spent away from each other. But luckily, they had more time (so much time) for that later, so he pulled away and kissed her cheek before reaching behind her for her suitcase.

She was left breathless but it didn’t stop him from holding out his arm for her to take. “Shall we?” He asked after picking up the forgotten sign.

She smiled and took his arm, resting her head against his shoulder as they walked. “I think I’m going to hang that up in my room.” She giggled into his jacket.

“Ugh, so sentimental,” he teased as they walked towards the exit.

“Said the man who made me a welcome home sign.”

He couldn’t argue with her so all he could do was wrap his arm around her and pull her closer as they walked to his car.


“Yeah, hi. We’ll have one large cheese with green peppers and mushrooms…and do you have flatbread crust? You don’t? Okay well then just the large pizza and a Caesar salad. For delivery. Thanks.” Jeff ended his call to the pizza place around the corner while Annie and Britta were chatting and catching up on the futon in Apartment 303.

“Seriously, Jeff? You’re getting a salad?” Britta rolled her eyes while clutching a pillow in her lap.

“Some of us work hard to keep up their physique, Britta,” he snarked back.

“But it’s my welcome home party, Jeff! You can’t indulge just this once?” Annie batted her eyelashes at him as he twirled one of the recliners towards the two women.

“I’d hardly call this a party, Annie. It’s just the three of us, pizza, some sad looking balloons, and Britta’s welcome home banner.” A brief moment of panic flooded his features before he added, “But we can throw you one! If you want. We can--”

“No! Jeff, I already told you, I don’t want a party. This is perfect. I’m here with two of my favorite people and that’s all I need.”

Jeff visibly relaxed and then blushed when Annie added, “Although I think you two owe me some new puffy paint,” when she looked up at Britta’s handy work.

“Yeah, yeah. I’m sure Jeff will drive to the craft store first thing in the morning, but—”


“—that doesn’t matter because I have this!” Britta pulled out a bottle of champagne from beside the futon.

“Aww, yay!” Annie clapped happily. “Britta, will you do the honors?”

“Already on it,” she hopped up and headed to the kitchen for three champagne glasses.

While Britta was away, Annie got up to quickly kiss Jeff on the cheek before she took her seat on the couch. “Thank you for tonight. And for making sure Britta didn’t turn this place into an animal sanctuary while I was gone.”

Jeff smirked. “Yeah, well, it wasn’t too hard. She can barely afford to keep the three cats she has alive.”

Annie laughed just as Britta came in the room with the glasses. She stood between Jeff and Annie and popped the champagne and then quickly poured the bubbly into the three glasses. “Cheers to Annie!” Britta proclaimed with her drink held high. “Congratulations and welcome home.”

“And congrats to the FBI for getting the one and only Annie Edison on their side,” Jeff added smiling proudly.

Annie blushed and shook her head, but continued to smile as she held her drink and said “Cheers to you two for being so adorable and sweet. And here’s to the future,” she was sure to look at Jeff for the last part of her toast. They all took a sip of champagne, and settled back into their seats. “It’s good to be home,” Annie smiled over her glass.

They continued to talk as they waited for their pizza to arrive. Britta put on some music at some point and she and Annie twirled together in their small living room. Jeff watched from the side and discretely recorded a video that would be posted to Facebook for their friends to see (much, much later). At some point during the third rendition of Jesse’s Girl, the buzzer went off, signaling the arrival of their pizza. Jeff grabbed his wallet and went downstairs to get the food (they stopped using the brick after Troy left last year).

After Jeff headed out the door, Annie and Britta collapsed onto the futon and laughed, out of breath from the dancing and singing. “I missed you, Britta,” Annie smiled.

“Aw, I missed you too,” she smiled back. “I don’t know how much more sulking I could have tolerated from walking hair gel over there,” she nodded towards the open door.

Annie scoffed, “Britta!”

“I’m just speaking the truth!” She smirked at Annie’s obvious blush. “But seriously,” she nudged Annie’s knee with her own. “What’s the plan for you two? Have you guys talked about it?”

Annie glanced at the door, making sure Jeff wasn’t coming back through. “Yes, we’ve talked a lot actually,” she glanced and smiled slightly at the floor. “We want to make this work,” she shrugged. “We’re not sure where I’ll be in a year, but we’re not going to let that stop us. I have to finish up at Greendale and get some more work experience before decisions are made. So, we’ll see.” She looked at Britta and smiled.

Britta smiled back sincerely. “That’s good. I’m happy for you guys.”

In the next moment, Jeff came through the door with pizza and his salad, “Ugh. The pizza guy was creepier than the last time.”


It was approaching midnight when Jeff was dozing in his chair, Annie was yawning, and Britta rolled onto the floor after falling asleep curled up on the futon. They were watching reruns of Parks and Recreation for a little while after they ate and soon enough, all of the dancing and travelling caught up with them.

As Britta lied on the floor, she made the decision to go to bed. “Alright, you guys. I need sleep.” She picked herself up and went to hug Annie. “Night, Annie. See you in the morning.” After breaking from their hug she smiled and said “It feels good saying that again.” Annie ‘awed’ as Britta walk towards her room, which used to be Abed’s. “Night, Jeff. I’ll probably see you in the morning too,” she snorted without looking back and then closed the door.

Jeff rolled his eyes, but he couldn’t hide the slight blush that crept across his face. He hated that Britta implied that he would be sleeping over because he truly didn’t know if that’s what Annie wanted. Of course, he wanted to stay, because he was still really missing her. But maybe she wanted to have her room to herself after being away for so long.

“Well, I’m sure you want to get some sleep,” Jeff said as he got up from the recliner. “I should probably get going—”

Annie laughed and took both of his hands in hers and pulled him towards her bedroom. “Don’t even think about it,” she said, making him smile wide.

He shut the door as Annie collapsed onto her bed, “Oh, I’ve missed my bed so much.”

“You know, my bed misses you,” Jeff said as he climbed onto the bed, hovering over Annie who was sprawled out.

“Oh, I miss your bed too! We’ll have to catch up sometime soon.”

“Another time. Because I think we have some catching up to do,” he smirked as he leaned down to kiss her. They melted into each other and felt the heat of their bodies mingle. Their mouths slid together and their hands roamed continuously over one another. “Annie, you feel amazing,” Jeff breathed.

“So do you,” she held her arms around his neck.

They spent the rest of their night catching up, until the early hours of the morning.