Jeff had actually done well to block out his second thoughts until now. But since he was driving to Annie's apartment and would start their first date any moment, those doubts seemed ready to make a last stand.
After three years of doubts, he figured it wouldn't be that easy to kill them. Even finally asking her out on a date a few days ago wasn't enough, apparently. But then again, he only told her he was tired of resisting the urge to be with her and at least wanted to take her out once. Plus, since it was November 2012, he said they'd have time to fix things before graduation if it went wrong.
Although Jeff said he wanted to be with Annie, he didn't say anything about being her boyfriend or being in love with her or how he wanted to be better for her. At the time, he thought he was being smart by not setting the bar too high for her, so they could take it slow. But now he feared that he didn't say it because he didn't really feel it, or would still run away if he realized he did – making this entire date a prelude for heartbreak.
Jeff told himself he held back all this time to protect Annie, although his denial's and lies wound up hurting her more until he had enough of it. Yet since he was really here now, there was no way left to stop himself from eventually hurting her. Whether he did it with a bad date, a failed relationship, a bad breakup or something else down the road, there was no more wiggle room out of it. The only way to stop it was to stay together forever, and even Jeff wasn't so far gone to imagine that happening yet….and what did that say about him?
When Jeff finally parked outside the apartment, he had to will himself to get out of the car. But as he walked to the front door, he wondered why he was here. Did he just ask her out so she wouldn't bug him about their….thing all the way until May 2013? Was he under one of those Annie spells he often fell into – and why was this one more powerful than the others? Did he secretly hope it went bad so Annie would be convinced they could only be friends? Or secretly wish it went great so they could have a relationship – and if so, why did he still want that a secret even now?
When Jeff walked up the steps to Annie's floor, he cursed himself for being such a girl. Jeff Winger did not panic this much, since Jeff Winger was the man in everything. But even talking in the third person wasn't lifting him up enough now. After all, this was a situation that Jeff Winger had never been in before – or at least not one he wanted to get right this badly. And if it went wrong, he would actually care if someone else got hurt…and he wasn't sure she was the only one who would get hurt.
When Jeff got to the hallway, he was more willing to admit he didn't know what he was doing. And if he could screw things up when he fully knew what he was doing, there were no limits to how bad this could go. Sure, he had been on dates before, but they didn't have…..this much at stake. He excelled when he just wanted to charm someone, have sex and be done with them – but the one thing he knew was that he never wanted to use and throw away Annie like that. Yet if he couldn't….what else was he good for?
He was over thinking this, which he almost never did. People like Annie could get away with that, yet Jeff wasn't them. However, the alternative was putting in his usual minimal effort, which just wasn't an option here. So by the time Jeff arrived at Annie's door, he resigned himself to being lost and clueless. Yet when he banged his hand against the door in frustration in a few times – a.k.a. accidentally knocked – he realized he was out of time.
There really was no turning back and no running away from disaster now. It would probably start the minute Annie came out and showed off her outfit. It was probably ungodly gorgeous and sexy, along with the rest of her – which would likely make Jeff want to do her then and there, skip dinner and start this whole thing off on the wrong foot. Or it would be just another ordinary cardigan – which would make Jeff disappointed that it wasn't sexy, make him blurt something out about her still being a child, and start this whole thing off on an even worse foot. No matter what, Jeff was bound to be wildly inappropriate and disappoint/infuriate Annie from minute one.
But he couldn't say something sexist or condescending if he couldn't see her. Fortunately, he figured this out a split second before the door opened, closing his eyes just in time.
"Hey….Jeff?" he heard Annie ask. Jeff just stayed quiet with his eyes closed, breathing steadily. But when his nose got within range of Annie's perfume, he settled for breathing with his mouth to avoid temptation. At least using his mouth to do that was keeping him from talking.
God, if he was trying not to talk, this was getting really ridiculous. Yet it was getting so ridiculous that explaining himself, or stopping this plan now, would just be more humiliating. So he doubled down, kept his eyes closed and hoped this would all go away on its own. Of course, having Annie right there probably wouldn't help that much. "Jeff, why do you have your eyes closed?" she finally asked.
"Oh, they….are, are they?" was all Jeff could say – but at least it made him close his eyes deeper in frustration. "Yes, they….never mind, hold on," Annie answered, then Jeff heard, "Abed, what date movie cliché is Jeff acting out?"
"It looks like the one where Jeff's insecurities have made him too nervous to talk, or to even look at you," Jeff heard Abed nail down. "Or he might have suffered an eye injury and is trying to hide it so he doesn't cancel, leading to a hilarious, life threatening driving scene. That actually does sound more in character for Jeff." Now Jeff slapped his forehead in frustration, which at least helped cover his eyes up further. "But his eyes would have been swollen, and that forehead slap would have made pus explode all over his hand and Annie's dress….yet it didn't. So we've narrowed down that this isn't an R-rated date…..interesting."
"Ew, Abed, I'm still planning to eat later, okay? You can gross me out all you want when I get back." So she was planning to get back and not have sex….unless she wanted it in her apartment – with Troy and Abed still inside. Talk about out of character. But before Jeff deluded himself more, he felt Annie's hand on his chest, then stepped back and soon heard Annie close the door behind her.
"Jeff…..are you really that nervous just to see me?" he heard Annie inquire. There was no really good way to answer that…..maybe joking about that would buy him time. "I refuse to answer on the grounds that people other than me will think it's really stupid," he tried to make sound clever.
"Come on, you haven't held back on saying dumb stuff before. Not that I'm saying that in a bad way! Well, not entirely," Annie corrected.
"Well, that was different…..it's all different now. Not bad different….but I'm probably making it bad different now, just like I thought." That wasn't exactly buying time and appeasing Annie. If Jeff couldn't even do that much, he really was screwed whether he opened his eyes, went on this date, let Annie down worse than ever, blew his one shot at finally doing right by her….or not.
But after several seconds, he didn't hear Annie yell or cry. In fact, he heard her chuckle a little – and could swear he even heard her light up, if possible.
"You know, this really is different! You know how you always tease me for being the Disney princess? Well, Disney princesses need kisses to make them open their eyes and wake up….but you're the only one of us who's needed that." Wait, he needed what? "Plus we should get this out of the way before dinner anyway…."
She was serious….she was going to Snow White and Sleeping Beauty him! Surely this had to backfire in some way.
But as per usual, Annie's lips erased all traces of Jeff's thoughts.
She broke off briefly, hoping to coax him into kissing back. And since she'd already kissed him and his eyes were closed anyway….
The kiss was actually the calmest one they'd ever had – making Jeff kick himself again that they didn't kiss when he asked Annie out. Not to mention all the kicking he owed himself for not kissing her for over two years. He actually felt her smile just before she broke off for keeps – and now Jeff really had no choice but to look at her.
Like his Disney princess brethren, the kiss opened Jeff's eyes and filled his newfound eyesight with Annie's smiling face. This immediately made him regret his decision a lot less. Yet she soon stepped back to let Jeff take a look at the rest of her.
After all this buildup and worry, Jeff was taken aback to see…..how modest Annie's attire was. It was a light flowery purple dress which showed off a fair amount of her legs, was form fitting, and yet she could breathe in it. It had some aspects of Annie's awkward fashion sense of years past….but it still looked grownup on her anyway.
Jeff was worried about Annie looking too childish and girly, or about her looking too sexy for him to contain himself. But instead, she was something in between…..bringing to mind who she used to be and still was in a way, as well as who she was now and how far she had come. She was a blossoming adult now, yet Jeff still saw the same Annie he had…..come to value over the last few years.
He finally looked back to her eyes and smile, both of which were still wide – yet now showed some of their own nerves in them. Since Jeff hadn't actually said what he thought about her looks, of course she was getting nervous. And despite all of that, Annie was still keeping her eyes bright and her smile warm. Despite the anxiety she must be feeling, she was powering through it to stay happy and confident….and didn't that say everything about her?
This was obviously uncharted territory for Annie as well. However, she was always far more fearless than Jeff….or at least more willing to face her fears. Plus since she accepted her feelings and modified them a lot earlier, she had more time to plan and imagine how this would go. Maybe Jeff didn't have to bare all the responsibility here after all….or worry so much about what would hurt her.
If Annie could survive everything Jeff put her through so far, the rest couldn't be that much harder for her. If he messed up, she would correct him and help him/guilt him into fixing it. Being a grown up and being in more….adult situations didn't have to corrupt her – not if he really wanted to do this right. And he did….God help him, he did.
"Well?" Annie made herself ask, still trying to be composed and brave, as always. It was time for that effort to be rewarded.
"You look perfect," Jeff finally answered, and it was true. He could have said beautiful, gorgeous, sexy and all kinds of other things – which she was. But perfect worked….well, perfectly. Not only did her appearance perfectly calm his fears, it was what Annie deserved to hear.
She had probably never been called perfect before, and there were so many times where she was maddeningly imperfect. However, Jeff had denied too long that she may be perfect for him anyway. He did so by denying that despite her faults, he still found her completely perfect just the way she was. But it might go a long way to admit it out loud now. "You look absolutely perfect," Jeff repeated to let it sink in for Annie, and it certainly seemed to work.
"Well….you would know about looking perfect, so I guess I'll take your word for it," Annie responded with a somewhat fluttery voice. Yet she recovered and coughed a bit, probably willing herself not to be girly and fawning. Still, if she failed, maybe it didn't have to be a deal breaker – not with everything else that balanced it out, both then and now. And that was a lot better to think about than anything Jeff was nervous about just five minutes ago.
"Okay…we got the kissing and the perfect looks out of the way. Might as well get through dinner while we're at it," Jeff offered, to which Annie nodded and walked with him side-by-side.
Along the way, Jeff looked over, seeing that Annie's arm was just shy of grazing his. She clearly knew that and was unsure whether to put them closer. But Jeff owed her one – well, more than one, yet first things first – so he put his arm in position for Annie to wrap her own around it.
Once Jeff and Annie were arm-in-arm for the remainder of the walk, they weren't nervous for the rest of the date. There were some brief nerves to end the night – but that was due to their anticipation right before their good night kiss/kisses, not their fear.