He'd never been one for grand gestures or romantic overtures, he'd certainly never thought that one day he would be planning one. It just wasn't his style, right? Sure, he could blame it on the post success euphoria, they did manage to save Greendale after all. He could probably also blame it on Shirley too, if he stared at the situation long enough and squinted his eyes, her and her talk about hearts and all. But the truth was, he was doing this all on his own, flying solo if you will. He really couldn't let anyone else get involved and the sappy part of his brain, the same one that wiped away a tear during the notebook, was becoming too large to control. He needed to do this, to go big and really make an impression, at least before his sappiness burst out and embarrassed him at exactly the wrong moment, he was still getting lingering looks from the Dean after all. It wasn't a well thought out plan, Jeff was well aware of that. It had a high chance of blowing up in his face and if worse came to worse there'd probably be no going back from this. But he had to try. Everything that had happened in the past week, Subway taking over the school, his brief engagement to Britta, finding a hobo from the 70s down in a basement, all these things were signs of the apocalypse, and Jeff would be damned if that meant not being able to say what he was truly feeling, at least before the end. Come on, he proposed to Britta for God's sake, if that's not on the Armageddon check list what else is?

That's right, he'd proposed to Britta.

Sure, they were probably never going to go through with it, and frankly being engaged to Britta felt more like they'd just bought furniture together rather than made a major life decision. But the fact of the matter was he had proposed. Jeff "nut up and die alone" Winger had proposed. And there wasn't any way of taking that back. That's why he had to go all out with this, to show her exactly what she meant to him, to show her that she was worth so much more than some half assed engagement. Worth more than some desperate attempt to cling on to the past and worth so more than he could ever really deserve. But that's why he was here wasn't it? Because she didn't care if he thought he wasn't worth it, she didn't care that he'd taken the best years of her life, she still loved him despite all of his flaws and despite his cowardice. That was what he'd taken away from her Winger speech down in the hidden computer lab, that he had to respect her enough to let her want what she wants, even if he thought it would kill her in the end. That she was strong enough to deal with whatever he could throw at her, because she'd been doing it for years. And even Jeff had to admit, she'd gotten pretty good at it.

So that was why he was here, standing outside her apartment building in his nicest suit, a bouquet of flowers and a horse drawn carriage ready to take them away on their date, a secluded picnic he'd personally set up that over looked the river and looked beautiful in the moonlight. Sure, some parts were overkill, but he'd PROPOSED, he had to do something to top that. He actually hadn't even asked her out yet, but was sure the spectacle of it all would win her over, Jeff Winger doesn't exactly do this for everyone you know.

He let out a small breath as he saw her open the door, the brick used to prop it open now sailing around the world with his good friend and his minor celebrity shipmate. She was dressed in her night gown and had her hair down, draped along her shoulders. He probably should have told her to get dressed at least. As she stepped towards him, her eyes a mix of surprise and confusion, he couldn't help but edge back, his body already too conditioned to the idea of running away. But this was something he had to do, something he needed to do, to make everything right, her speech pretty much confirmed it. She wanted him, and now finally he was ready to let her have him.

"What is all this?"

"It's me. It's me saying I'm ready, ready to do this for real."

"What do yo- is that a horse?!" her eyes widened as her stepped towards the animal, an animal Jeff had silently named Thug Hunter, though he wasn't going to ruin the mood like that.

"Yeah, it's our ride." A satisfying smirk appearing on his lips.

"Our what? Our ride for what exactly?" Her voice wavered as she wandered over to the carriage, her fingers trailing along its side.

"Our date Milady."

She froze as he said it, the silence of the night echoing between them.

"Date? I, are you serious?" she turned to him as she said it. But it wasn't quite the look Jeff had been expecting. He was fully prepared for her to start swooning, her Disney eyes going into full overdrive or for her to begin squealing uncontrollably. But the look she was giving him, what was that? It wasn't in any of his prepared responses, what could it be. It wouldn't, no it couldn't be... pity?

He'd just have to power though and stick to the plan, he was expecting some setbacks and he knew that in the end, like so many other things, the fate of this evening would be decided by his words. He took a deep breath, pushing his chest out just a little as he did so, and began.

"Annie, I've know you for over 4 years now, and I've never taken you as seriously as I should have. You are, the weirdest, coolest, most sincere person I know and what scares me the most, is how good you make me want to be." He knew that opener was good, why fix what isn't broken right?

"I want you to know just how much you mean to me, and how much better you've made me, as both a friend and as a man." he stepped forward, his eyes staring directly into hers, time to go for gold.

"This week has been one of the strangest in my life, and at Greendale that's saying something. There was so much going on in my head, so much crap and noise that I couldn't take the time to see what was really in front of me."

"Which was?" She was directly in front of him now, gazing up at him through her eye lashes.

"You," pause for dramatic effect, "You, you've always been there, stood by me through some of my lowest moments. You've picked me up time and time again and forced me to be a man I didn't even know I could be. But you knew. You always knew. From the very beginning you saw something in me that no one else did. I've been selfish, and stupid, and I never gave into those feelings because some part of me thought that they were coming from a child. A love-struck teeny bopper who didn't understand how bad I was. But I get it now. I understand everything. I finally understand what you meant back there when you said 'we have to respect each other enough to let each other want what we want'. I respect you Annie, I can't keep dismissing your decisions because of my hang ups. You're an adult and I have to stop trying to protect you, even if the person I'm trying to protect you from is me. What I'm trying to sa-"

Her hand shot up in front of his face, stopping his flow. Shit. She should be close to tears right now, he's baring his soul at the moment couldn't she at least wait for him to finish before she jumped into his arms? He shifted his weight and caught a glimpse of her face from behind her hand. Her expression hadn't changed.

"Jeff, what I said in the computer lab, that wasn't what I meant..."