Jeff had never gone more than four dates without having sex before. And even that was at the start of his sexual career – when he still needed an effort to seduce women. That helped turn him off work altogether, as he then used quicker, casual sex to perfect his sex God magic and never looked back.
Admitting it once took four dates to get sex was pretty grueling. But once Jeff finally got together with Annie, he made himself tell her anyway. After all, she had to know why he wouldn't sleep with her before the fourth date either.
Now that Jeff finally had Annie, he couldn't treat her like every other Winger girl – even though he'd never waited three years to date Winger girls. But he'd rarely wanted to be in a real, healthy relationship with a Winger girl either.
To him, if he could have five regular dates with Annie without sex on the table, it would show him he could handle a real relationship after all. He had always figured dating without sex was too hard and lame. Yet if he could do that with Annie before getting to the sex, it would clear a big psychological hurdle for him.
Annie still believed Jeff was capable of real relationship stuff, even if they had sex right away. But Jeff needed to prove to himself he could do it. After 15+ years of believing he couldn't, it wouldn't be a quick fix – and Jeff didn't want one of those this time. He wanted to put in the effort and become a good boyfriend, before he became Annie's greatest lover in this or any other lifetime.
Once he sold it that way, Annie agreed to the terms. They could still make out, since Jeff was tired of having that much self control. Otherwise, their first five dates would be more romantic than sexual, so Jeff would know that he could be as well.
Even in past relationships, Jeff very rarely went out without aiming for sex. As if this first date wasn't different or nerve-wracking enough. He owed Annie a dream first date – but not so dreamy that they'd both lose control. Could he give Annie that much without wanting more?
Annie was nervous too, as she wore a modest blue dress without showing much skin – so she wouldn't threaten Jeff's self control. For his part, Jeff threw on a suit that actually cost under 60 bucks – so he was basically in rags.
The awkwardness remained after they reached their dinner table. Neither one knew how to act or how to even begin. Just to break the ice, Annie gave some behind-the-scenes scoop from Troy and Abed's latest apartment movie shoot. Maybe it wasn't ideal date conversation, but she needed something to go on.
Jeff did laugh, since Annie being annoyed over Troy and Abed's antics always amused him. Then again, Annie noted that Jeff's annoyance over doing things at Greendale amused her. Yet in a way, they both thought they were above Greendale insanity and tried to be all business – Annie with her studies and Jeff with his laziness. But they always got dragged in and became crazier than everyone by the end.
Seeing they were alike that way made them both relaxed – as it often did when they discovered they had things in common. Focusing on their differences had cost them too much time already. When they resolved to stop doing that, the conversation got easier and more freeing – like they were back at Greendale during one of their good days.
Jeff wished he'd had more one-on-one talks and private time with Annie in the past. However, whenever they had it before, he always had to hold back and walk on eggshells in one way or another. But now that their cards were finally on the table, he didn't have to hide anything anymore.
He could let himself laugh with Annie, without worrying about laughing too hard. He could stare at Annie without worrying if he was staring too long – or too affectionately. He no longer had to worry about Annie reading too much into his actions – or reading just the right amount.
Soon, this wasn't like a first date at all. It was just like a regular talk between Jeff and Annie – only longer, more truthful and with far fancier food and scenery. They could be themselves, talk about the things they usually talked about, and not have to repress any looks, smiles or affection.
All Jeff had to repress was the need to take Annie to his bed. Instead, he took her back to her apartment, feeling…..content to end it there. If not satisfied in every way. But considering how much fun he'd had without sex on his mind, there was no need to push it.
Even when Annie kissed him, Jeff could kiss back, let out some long overdue passion, and still break away without going for her boobs. It was enough in the moment – and if he still fantasized about doing more, that was what bedtime was for.
Jeff had proven he and Annie could have a nice meal out. Now he thought they should have a nice meal in next. He invited her to his apartment for a nice home-cooked meal, where ideally, he would wow her with his hidden cooking skills. He would wine and dine her in private, then take in a movie or TV show on the couch, and it would be a nice, intimate evening all around.
At least that was the plan.
Instead of being an awesome chef, however, Jeff wasted half the time trying to find the right ingredients. Then he all but burned the place down when he waited too long to check on the food. The smoke cleared by the time Annie arrived, but there wasn't much left that was edible.
Yet instead of being let down, Annie looked through the kitchen and found some regular food to fill the gap. Although it wasn't the romantic, intimate dinner Jeff wanted for her, the mere fact he tried to make one was enough for Annie. No one ever put in that much effort for her on a date before – even if it was mostly a failure.
Jeff put off sex to put in an effort as a real boyfriend first. In that regard, this was certainly a big step forward.
At the least, talking about his failed cooking and making Annie laugh at it got them through dinner. This made them relaxed enough to watch DVR recordings of Jeff's favorite shows – some of which Annie already watched, and a few of which she even liked.
In this night with a home-cooked dinner and a show, there was more show than dinner. But as Annie laid her head on Jeff's shoulder and drifted into a nap, Jeff felt he got more than his money's worth.
Jeff figured the next step was to include a real activity with their date. After all, they needed things they could enjoy together without the group's involvement. But Annie's favorite activity was learning, which Jeff would not do outside of Greendale – even under threat of Disney face.
At least not school learning, anyway.
The way to Annie's heart was to teach her things and let her be the model student she was. And there was one thing Jeff was qualified to teach her. So after dinner, Jeff took Annie to his favorite pool hall.
Jeff was taking a risk, considering the last time Annie saw him play pool. Reminders of the first time Annie saw Jeff naked might not help the whole "no sex yet" plan. However, once Jeff started teaching Annie how to play pool, she focused on the lessons and was all business – otherwise she wouldn't be Annie.
There were some complications when Jeff got behind Annie to set up her shots. But Annie managed not to quiver at Jeff pressing up against her – and vice versa. Besides, Jeff's ego was more inflated than his other parts, since he got to show off his pool skills and look like he knew more than Annie for once.
Unfortunately for his ego, Annie was an incredibly quick learner outside of school too.
Before the night was out, Jeff actually needed an effort to beat Annie. She even almost beat him in their last game, and was pissed for most of the ride home that she didn't – despite how she shouldn't have come close. Yet Annie did try to make it look like his teaching, not her natural studying, helped her learn so well.
But Jeff knew better than that, and so did Annie. She could learn and excel in anything at a moment's notice, even if she was out of her comfort zone. And that could apply to other areas too – ones involving different types of balls and round, supple, naked objects.
Needless to say, Jeff exhausted himself more in the bedroom that night than he did at pool, although he was in bed alone. But he wouldn't be dumb enough to do that much longer.
The most special part of this date was entirely unplanned, and all Annie's fault. Well, Jeff bore some blame too.
He was content to just drive Annie home after dinner – yet he was the one who looked at the courthouse as they drove past it, as he often did. But he didn't usually have guests to see him do it.
It was inevitable that Annie would catch him looking – and figure out he hadn't been inside the courthouse, or any courtroom, since he was exposed as a fraud. And it was all too predictable that Annie would want them to go inside now. Yet despite knowing what was coming, Jeff couldn't stop it anyway.
Annie was excited to see Jeff in his old workspace again, as he took her through the courthouse and recounted some of his greatest victories and plea bargains. But she was more enthralled on the outside than he was becoming on the inside.
In a few months, Jeff could become a lawyer again – the whole reason he endured Greendale to begin with. But now that he was finally back here, it felt….weird. And when Annie found an empty courtroom for them to sneak into, it felt even weirder.
For the first time in four years, Jeff Winger approached the bench. Of course, there was no judge to wow, no opposing lawyer to get trounced, and no jury to fall for it. There was just Annie sitting in the jury box, envisioning Jeff giving a Winger speech in a court of law. And as many times as Jeff envisioned that too, picturing it now was….almost alien to him.
Annie noticed Jeff's distant look and wondered what was wrong. But Jeff didn't know if anything was wrong, per se. It just hit him how close he was to having his old life back – and how it really didn't blend in with his new one. And how for the first time, he felt it said more negative things about his old life than his new one.
Jeff still wanted that old life back, since he needed to work and afford his flawless wardrobe. But just having that old job again didn't seem like enough – not like he thought it would be four, three, two or even one year ago.
Yet could he blend the old Jeff's old routine, and the new Jeff's more fulfilling life, to create a better, hybrid Jeff? Was it even possible that he could be a lawyer and still be the better Jeff he'd become at Greendale? And if he really was more evolved, should he even want to still be a lawyer?
In typical Jeff fashion, he'd buried these troubling questions and ignored them for some time. But they had grown long enough that they finally just burst out of him. He felt embarrassed and ashamed to look that doubtful, uncertain and sappy in front of anyone – much less himself and Annie.
But Annie didn't go 'awww' at how he showed emotions, or give him a syrupy pep talk. Instead, she shared how she felt the exact same way herself.
In a few months, she would graduate and try to start her career in health care administration – the whole reason she endured Greendale to begin with. But now that it was within reach, it didn't seem like enough – not like she thought it would be four, three, two or even one year ago. And she didn't know if the life she'd always wanted gelled with the better life she'd stumbled onto at Greendale.
She still wanted her old dreams, since she needed to start a career and keep affording her half of the rent. But she didn't know if she could have that life and still be the better Annie she'd become. And if she really was more evolved, should she even want that life anymore?
Seeing himself reflected in Annie always stunned Jeff, but not as much as it did now. So he went to the jury box and held her close, seeing how she'd never doubted herself like this before. But Jeff reminded her she never had so many friends to prop her up before, so she didn't have to figure things out alone. And Annie reminded Jeff he didn't have to either.
Right then, being this close to his old life felt much better to Jeff – because the best part of his new life was there with him. His ego and brilliance made him love his old life before. But now, it looked much better because Annie was there to make it better. Not that he was sappy enough to tell her that – he still had some masculinity.
But maybe he could keep the best parts of his old life and not let the worst parts ruin him. Even if he'd have to work to juggle old and new Jeff together. It might be worth it if it gave him more moments like this.
Annie got that epiphany the next day, when Jeff helped her visit her old rehab center for the first time since getting clean. When she saw where she started to put her life back together – and reunited with people who didn't abandon her in the process – she felt better about her path too.
A career in health care couldn't define her life anymore. But Annie still wanted to help make people healthy and whole again – like she became in rehab. In a way, she and Jeff would have the same job, in saving people at the end of their rope and giving them a way back up.
Of course, Jeff kept criminals from prison, and Annie's future hospital would heal some scumbags too. But they couldn't judge the people they helped, at least not enough to not do their jobs. And although they had two of the most despised professions in the world, Annie wanted to help make hers better – and now Jeff would want to do the same with his too.
This whole package of epiphanies was a turning point for Jeff and Annie. Neither of them had felt as close to each other, or anyone else, as they did after this extended, two-day date. And neither of them wanted to hold anything back anymore – especially behind closed doors.
Jeff and Annie still had to finish a record-setting fifth date before their first time. So this time, they finally went all out.
Jeff put on his very best suit, got the best table at the best restaurant in town, and would give Annie the full on Winger treatment. For her part, Annie bought the fanciest – and most revealing – red dress she could afford and feel comfortable in.
With the two of them looking so sexy, and with their wait almost over at last, it took some effort not to rush through dinner. But Jeff unleashed his full Winger charm to keep Annie entertained and distracted. And since Annie had dated more in the last month than in the last four years combined, she was more than a quick learner by now.
Although they had a fancy dinner and some wine, they made sure not to overdo it. They wanted to be at full strength when they got back to Jeff's apartment. And when they got there, they weren't too full or drunk for the main event.
The minute Annie closed the front door, Jeff pinned her against it and kissed her hungrily. They'd had a few make-out sessions against this door after past dates, but this time Jeff held nothing back. All that kept him from having her right there was that he wanted her in bed more.
When Annie's back hit the bed, Jeff got right back to work. Annie joined in, as she rubbed her hands all over his chest and stomach. Jeff's hands got grabby too, as one went down to her bare leg and the other approached her breast. That red dress was doing wondrous things for Annie's boobs – but they'd still look better without it.
Annie was on the same wave length, as she lowered the top of her dress to expose her bra-less chest. As Jeff gaped at it, Annie's hands went back to the bottom of his suit. She pulled it up to finally feel his bare skin and abs, though her hand remained close to his belt.
Jeff then had enough of staring, leaning down to put his mouth on Annie's breasts. After enjoying the first few tastes with his eyes closed, he opened them to see that Annie had her eyes closed as well, lost in her arousal. But as Jeff's mouth engulfed her nipple, she stared right at him as her hand drifted into his pants.
Jeff had Annie's glorious breast in his mouth, while her gorgeous blue eyes gave him the most loving, lustful gaze he could imagine. And on top of it, her small, warm hand was pumping his erection inside his pants. The taste, the sight, the friction and the….well, Annie of it all made Jeff wish this could last forever.
Instead, he only lasted two more pumps.
Jeff couldn't warn Annie, or himself, before he shot off in his pants and on her hand. He could only lay his face on her chest, as his sudden eruption consumed him. When it was over, he kept his face down, in vain hope that her boobs could swallow his head up.
Once reality set in, he got up, took a pair of sweatpants and went into the bathroom to change. He made sure to get several tissues for Annie, but he didn't stick around to see her use them. Jeff just went to the living room and stayed on the couch, stiff as a statue – to coin a now-sickening phrase.
He even stayed still when Annie came over and sat next to him. But it wasn't like she had any idea what to say either. Even she knew enough about this stuff to know how the wrong word could set Jeff off. So she merely stayed quiet with Jeff as the minutes passed.
At least a half-hour passed before someone finally said something. "Well, now you know," Jeff tossed out.
"Oh! Well, um, I know a lot of things, Jeff," Annie recovered from the shock.
"And now you also know what kind of power you have over me," Jeff added.
"Oh, I knew I had that. Disney face, remember?" Annie tried to laugh off.
"That's not like….this," Jeff burst their bubble. "Disney faces never made me…..that explosive! Not that quickly, anyway! And not in front of you!"
"We waited three years and five dates for this, Jeff. It kind of makes sense, really. Frankly, I'm surprised I didn't….lose it first!" Annie assured.
"But you didn't. You stayed under control….I didn't. And there you go," Jeff started. "When I tried to be romantic and boyfriend-y, I failed when it really counted. And when I did, I stayed quiet and shut you out, like I was my old self again." He took a breath and went on with a larger theory. "And when I screw up this whole relationship, I'll turn out the exact same way."
"Jeff, you don't know that," Annie frowned. "And you didn't screw up anything. Just because you….messed up one time doesn't mean you'll mess us up. And just because you waited five dates to have sex with me, it doesn't prove you won't mess us up either!"
"I just wanted to have as much faith in myself as you do in me. I thought this would help, but…." Jeff left hanging.
"Jeff, it took me four years to have the right kind of faith in you," Annie pointed out. "First I had way too much, then way too little, then I finally got the right balance. You will too. But you don't have to get it right from the start, you know," she offered.
"We've got so much ahead of us, and neither one of us is going anywhere. It took us four years to get here, and as long as we don't push each other away, we can take four more to get the other stuff right. We've got all the time in the world," Annie figured. "Even in this situation."
"How do you figure?" was all Jeff had.
"You think the whole night's over because you went off early?" Annie asked, without even a stammer or blush. "Jeff, it's Friday. It's only 10:00, and we don't have to go to school tomorrow. And I moved my Saturday chores and studying to Sunday, just for this weekend," she stressed. "Like I said….we've got all the time in the world."
Annie moved to kiss Jeff extra slowly, without making any other moves. More than enough time had gone by for him to 'recover,' but she didn't want to build him up again so quickly. So she settled for slow, gentle kissing to get him back in the mood. And after a while, it worked.
Jeff ultimately got himself to rise and take Annie back to bed. Unlike their stay there last time, they took their time and didn't grope each other right away. Although they tried Jeff's way of taking things slow for five weeks, Annie's slow methods were paying off even more.
Plus, since they'd drooled over each other's bodies in some way for four years, taking the time to savor and worship them was a far better payoff. And Jeff owed Annie some worship – of her body and other things —after all their setbacks.
He never doubted Annie had faith in him and their future together. He just thought he needed extra faith in himself to put them over the top. But maybe Annie's excessive faith could be enough for both of them until he caught up. It might be worth it if it gave him more moments like this.
Jeff and Annie indeed went five whole dates before having sex. But right after the fifth date, they didn't have sex, per se. For lack of a less clichéd term, they made love, even if they never uttered 'I love you.' But they could wait for that too.
In any case, they spent most of Saturday getting to the raw, head banging sex anyway.