Author's note: I haven't forgotten about this fic! I haven't had a lot of chance to update prior to this, but I'm hoping to get into a good rhythm with it now. Reviews would be appreciated!
He wasn't exactly sure when he'd decided it.
They'd been together for quite a long time, when he started looking at the rings in the shop windows with a little more longing.
He was often found trying to convince himself that 'nut up and die alone' was still the way forward, but how was he supposed to envision a future alone, when he'd fallen completely in love with Annie Edison?
She'd gotten under his skin, into his heart, and convinced him that he needed to propose – and for real this time.
Annie had completely flipped out, when she'd heard about his 'engagement' to Britta. He pleaded over and over again, that it was all just an act, because Abed had started to notice what was going on between the two of them, and he wanted to throw him off the scent…but it still stung like crazy, especially seeing as Britta wasn't aware he was a taken man, and had taken it all seriously.
Of course, he'd managed to convince her better since then; he could lawyer himself out of any situation, and although that often didn't work on the stubborn little firecracker that he called his girlfriend, it tended to finally work out in his favour after, a little convincing.
The summer had been the best time, and now they were back at Greendale, nobody seemed to really be batting an eyelid at the duo. The teaching staff wouldn't notice the relationship if they climbed up on the study table and had sex in front of everyone (and Jeff may, or may not, have pictured that in his head a couple of dozen times), and despite the fact Annie lived with both Abed and Britta, neither one seemed to have much of an inkling that anything was happening.
At least, Britta definitely didn't.
Abed? Neither one was too sure.
But, as time went by, Jeff had far more than just Abed on his mind.
He never quite figured out the time or the place to do it.
Taking her to a fancy restaurant and hiding it in something or other seemed too cliché. He could practically hear Abed shooting down every idea that passed through his head. Why did everything have to be so damn cheesy? Stupid movies, they ruined EVERY possible engagement scenario.
So, as it were, Jeff Winger knew he wanted to propose, but he had no plan.
Maybe they should tell the group first. They probably should, right?
Jeff found himself worrying about it more often than not, but luckily; Annie didn't seemed to have noticed just yet. She'd asked him multiple times if he was okay, but he wrote it off as stress, and she was buying it, all thanks to being too distracted by books, or whatever else.
Like right now.
She was sat studying, legs curled up on the couch, with her feet resting against his leg. There was a content, determined look on her face, and her nose scrunched up occasionally, as she concentrated hard. How did someone get to be so beautiful, and so smart, in equal measure?
With his mouth open like a fish, Jeff gawked at her. Not for the first time, he was thinking about how lucky he was to have her.
In his years as a student at Greendale, Jeff hadn't allowed himself to give in to her. She'd always been the most amazing woman to ever show any kind of interest in him, but he allowed himself to be freaked out by the age difference. A mere excuse to stop himself from admitting that he could fall in love, really.
As time went on, he had realized what an idiot he had been all that time. He'd missed out on opportunities to be with the most amazing woman, and he was so fucking lucky that she was still willing to give him the time of day. Anyone else probably wouldn't have waited for so long.
These days, it was clear that his insecurities got the better of him pretty often, and he sometimes wondered if she could do better. But, he loved her too much to let her go; he loved her enough to…
"Annie."
Wide, blue eyes looked up at him, but she only looked confused; maybe even a little concerned. His words sounded urgent, and maybe they were. This was what happened when he didn't have a plan.
There he was, hair hardly even styled; there she was, wearing a hoodie that he was pretty sure used to be his…it was just a casual, domestic moment. There was nothing at all special about it, and yet it was. It was special, because it was the two of them. And, that was why it felt right.
"I've been wanting to do this for awhile," Jeff began, reaching a hand into his pocket, as Annie closed her book, still visibly confused.
The petite brunette was reaching to place the book down on the coffee table, and as she went to move back, he was grabbing her wrist, gazing at her imploringly.
"Sometimes, I look at you, and I realize just how in love I am. Sometimes, I think about you, about us, about the future, and I…I feel good. Safe. I feel safe. I've never felt this way before, Annie - about anyone. So, I was wondering…"
He pulled his hand out of his pocket now, and her breath caught in her throat, as she saw him opening the small box. Was Jeff Winger about to do what she thought he was about to do?! Was she dreaming right now?
"Will you marry me?"
He barely heard her 'YES!' through her girlish shrieks, as she dived on him, but he did manage to catch her tiny hand in both of his, and slide the ring on her left hand, before they were both lost in a never ending spiral of kisses.
It wasn't until the next morning, when Annie woke up, and turned to him, that she asked the one question neither one of them had yet considered, in all their excitement.
"How are we supposed to tell the group?"
Jeff, not used to being awake so early, rubbed as his eyes and mumbled a confused, half-asleep "What?"
"They don't even know we're dating, Jeff. We've both been so worried about keeping this a secret, we haven't even told our best friends. How do we just drop in 'by the way, we're getting married'?"
He huffed a little, sitting up, suddenly aware of how bad that actually was. Shit.
"We send them a Save the Date, and hope they don't decide to hit us."
His new fiancée shrieked in indignation, as she climbed up off the bed, throwing a pillow in his general direction. It covered his face, and he grunted in complaint, letting it stay there a moment before he, too, got up off the bed.
"We got too deep into this fast, Annie. At some point, we should have told them, but we just kept forgetting. We kept…putting it off, I suppose," He shrugged, scratching at the back of his head. "I guess now would probably be a good time to tell them, huh?"