Work Header

Advanced Studies in Leaps of Faith

Work Text:

Advanced Studies in Leaps of Faith

Friday, June 15

The summer after third year was a little different for the study group, who each had five courses to make up for after their expulsion earlier in the year. Primary among those courses was Biology, which was easily the most difficult and time consuming, and also the course they were least able to focus on because every time they got together, the discussion quickly devolved into how much they just wanted to enjoy their summers.

But not every day was taken up by classes. Monday through Wednesday they were all at school, but they still had Thursdays, Fridays and weekends off with which to enjoy the beating sun, warm breezes and various summertime activities. For Jeff, that meant spending as much time as possible looking for other law firms to do contract work for, since his term with his old firm officially ended when he caused Alan to lose one of his wealthiest clients.

In fact, on this particular June afternoon, Jeff had just left what felt like one of dozens of job interviews with another local firm. Another ‘no’. Another, “We’ve heard about you. We’re not interested.”

With his blazer carefully folded and slung over one arm, and his tie loosened around his neck and his collar popped open, he wandered through downtown Greendale, feeling once again rejected, dejected and useless. Four years earlier he’d had it all. He’d had the job, the women and the life he’d always dreamed of. Now he was taking summer school classes at Greendale’s second-ranked community college and was spending his spare time with a group of misfits and screw-ups.

Okay, the misfits and screw-ups part didn’t suck so bad... but the rest certainly did.

He yanked his tie the rest of the way off and slung it over his coat on his arm, unbuttoning a few more buttons and relishing in the breeze hitting his skin. It was too hot to be out in a long-sleeved shirt and black slacks. Just like it was too hot to be worrying about where he was going to work when he graduated... or how he was going to continue paying for his apartment and car, and, you know, eating on a regular basis.

He squinted up at the sky. It was a gorgeous, clear blue day. The sun was beating down a little hotter than he would have liked, but he was hardly about to complain about it. The beautiful afternoon was the only thing keeping him from hopping in his Lexus and driving home to drown his sorrows, before jumping into another assignment for another course he should have finished months ago.

Had he mentioned he hated summer school? Because he really hated summer school.

He looked away from the sky and tried to blink the sun out of his eyes. He spotted an empty park bench and decided to take a rest and bask in the heat for a little bit. He carefully laid his blazer and tie out beside him before slipping into the free space where he went about rolling up the sleeves of his shirt so his forearms were bare. A part of him wanted to just take the shirt off too, but it was mid-afternoon and there were kids around.

He pulled out his phone and began playing Angry Birds.

“It’s 95 degrees and you’re still playing on that stupid phone.” He squinted up to see the culprit who had interrupted his game.

“It’s 95 degrees and you’re still wearing a cardigan,” he threw back. Annie grinned and peered to the spot next to him.

“Blazer and tie on a dirty bench, open collar, sleeves rolled up... you just came from an interview.”

“Good extrapolation,” Jeff said, turning back to his phone. Annie slid into the seat next to him, shrugging off her cardigan and reaching across his lap to place it on top of his discarded clothes.

“Didn’t go well?”

“Another good extrapolation.” He dropped his phone onto the pile next to him with a sigh.

“What happened?” Jeff bit the inside of his lip and looked down at his lap, which was uncomfortably warm beneath the dark fabric and searing sun.

“Same as usual,” he divulged. He peeked over at her. Her concern was, as usual, plastered all over her face. “This might not happen for me, Annie.” She shook her head and reached into his lap, grabbing one of his hands encouragingly.

“Of course it’s going to happen. You just need to keep going to interviews and keep showing people how great you can be.” He frowned down at her their entwined hands.

“I don’t think “community college changed me” is going to work with this crowd, Annie. I think they’re more interested in what’s on paper: ex-lawyer caught cheating and lying, soon to be disbarred.” Annie wrapped her arm around one of his and gave it a little squeeze.

“It’s going to work out Jeff. I promise.” He looked back at her.

“How do you know?” She offered a small smile.

“Because I know you. And I know it’s only a matter of time before someone else sees how great you are.” Jeff’s lips quirked up slightly.

“You’re a good liar.” She rolled her eyes.

“I’m not lying.” She pulled herself to her feet. “But I am going to get ice cream. Interested?” She held her hand out to him. Jeff groaned.

“Ugh, all the carbs!” She rolled her eyes.

“Come on! Throw your coat and everything in your car, and come spend the day with me. You can sulk and drink yourself to sleep later.” Jeff winced.

“You really do know me too well.” She giggled and grabbed her cardigan, then held her hand out insistently to him again.

“Come on, Jeff. You know you wanna. That nice, cold ice cream is just taunting you.” He groaned and grabbed her hand, allowing her to pull him up. Together, the two walked across the street and stowed their discarded clothes in the back seat of his car (his, on a wooden hangar that he kept there for emergencies), before heading back out to the pathway that looped around and through the public gardens where a vendor was selling ice cream.

“If any of this gets on my white shirt, I’m holding you personally responsible,” he said once they both had cones. Jeff’s held a heaping scoop of chocolate while Annie’s was nearly toppling over with strawberry. She licked a drip away and stuck her strawberry tongue out at him. “Mature,” he teased.

“Says the guy holding a third party responsible for his ice cream disasters,” she shot back. He just chuckled and took a lick, catching a drip just before it had a chance to cause real damage.

Together, the two walked and talked amiably as they ate their ice cream. If Jeff was being totally honest, he would admit that this was kind of nice, especially after the terrible time he’d had at his interview. Annie was fun and free and didn’t mind being a little bit silly. She was also beautiful in her flowered sundress with her hair pulled back in a high ponytail and her tongue darting out every-so-often to capture more of the sweet snack. Jeff tried to put the kibosh on those particular thoughts, but it became difficult when a drip made its way over her hand and wrist, forcing her lick it off of her own skin. He barely suppressed a groan at the sight.

As the two wandered deeper into the gardens, Annie became easily enamored with the flowers that were now in full bloom.

“It’s so beautiful in here,” she gushed. “I never come here. I don’t know why not.” Jeff smiled at the way she was talking more to herself than to him. It was a cute little habit she had when she completely let het guard down, and it was more than a little endearing. He popped the end of his cone in his mouth and crunched it away, feeling full and cooled down, and significantly more jovial than he had been just twenty minutes earlier. Annie tended to have that effect on him. Well, Annie and a beautiful summer’s day spent outside.

But yea, it was mostly just Annie.


Thursday, June 28

 “Okay, first rule: nobody knows about this. Cool?” Annie rolled her eyes.


“Good. Second rule: if I suck, and I will suck, you do not get to laugh at me.” She giggled this time.

“Jeff, it’s not a big deal!”

“THIRD RULE,” he interrupted. “If I hurt myself, we’re coming up with an alternate story, and you are not allowed to stray from it. Deal?”

“Fine, Jeff. Geez. Would you calm down a little? This is supposed to be fun!” Jeff sighed and acquiesced, slightly.

“I know—but it’ll be more fun if we both follow all of my rules. Capisce?”

“Capisce?” she teased. “What, are we in the mafia now?”

“Well, you did make me an offer I couldn’t refuse,” he said with a smirk.

“Alright, alright—fine with the rules. If it’ll make you stop being such a girl!” Jeff shook his head.

“I’m adding an addendum to number two—no teasing.” She scoffed.

“You teased me the moment you got here.”

“Okay, no teasing me.

“Do you want to do this or not, Jeff?” she asked. Jeff hesitated a moment. “Jeff...”

“Yes!” he said quickly. “Yes, I do. Please.” She watched him critically for a moment to see if he was planning on making any more last-minute additions to his list. Satisfied that he really was done, she reached down and picked up the ball laying at her feet.

“Okay. Then let’s learn how to throw a ball.” Jeff offered her a small, thankful smile before backing away a few steps to create some space.

The group had known for some time that Jeff, while good a number of things, was painfully hopeless when it came to throwing balls. He couldn’t throw a baseball, or a football. He could sort of pass a basketball, but that’s because it was only ever thrown short distances. When it came to long-distance throwing, he was useless. He’d never played on any sports teams as a kid, and he blamed having a sport-phobic mother for his inability to do anything other than dribble a ball and occasionally, if he was lucky, get it in a basket.

That summer, Annie casually let it slip that she used to play competitive softball. Now, baseball (or softball) was not a sport that interested Jeff in the least. As far as he was concerned, it was generally just a bunch of old fat guys standing around and scratching their balls, waiting for a ball to come vaguely in their direction. But they did need to throw... and he figured asking Annie for help would be less embarrassing than, say, asking Troy, the former quarterback (a fact that definitely did not intimidate Jeff at all).

Annie, naturally, had jumped at the opportunity, prefacing their lesson with the disclaimer that she hadn’t played since high school, so she was probably a little bit rusty.

But now that they were actually on the ball field (and Annie was dressed in a cute pair of capri pants, an old baseball jersey and cap), whatever skills she’d lost over the years were quickly returning to her. For a moment, Jeff thought he might have actually preferred to be there with Troy and a football. At least then he wouldn’t be getting showed up by a girl.

Jeff had a catcher’s mitt on his right hand, which only helped him catch the ball some of the time. Apparently he was an even worse catcher than he was a thrower.

“Okay, just ease your arm back and throw,” Annie instructed. “Not too hard, you don’t want to hurt your arm.” Jeff rolled his eyes.

“I’m sure I’ll survive,” he said with about as much machismo as he could produce while holding a softball. He followed her instructions though, and lobbed the ball as well as he could in her... sort of, almost, general-ish direction. She ran the twelve feet to her left where it landed to retrieve it.

“That was good!” she praised him as she collected the ball. Jeff grimaced.

“That was awful,” he dished. She shook her head adamantly.

“No it wasn’t. Your distance was good, it’s just your aim that needs a little work.”

“A little?” he asked, incredulous.

“Okay, maybe more than a little—but it was a good first attempt. Let’s try again.”

The two went back and forth like this for well over an hour, Jeff’s attempts getting better and better each time, both at throwing and catching. Jeff had to admit that Annie was kind of a good teacher when it came to this sort of thing. She was endlessly patient, she talked about technique and how not to hurt yourself, and she was encouraging even when she probably didn’t need to be.

Jeff was almost surprised to realize that he was actually having fun. Having fun throwing a ball. This was one hell of an unexpected progression for him.

As Jeff and Annie finally grew weary of tossing the ball back and forth, they both met in the middle.

“You’re doing such a good job!” Annie gushed. “I’m so proud of you.” Jeff couldn’t help the small smile that found its way onto his lips. As much as he wanted to be sarcastic and ruin the moment, he just didn’t have it in him to do that. Instead, he flopped down onto the grass and laid on his back. Annie did the same, laying beside him with the ball in the middle.

“You’re a good teacher,” he said once she was settled. She peered over at him with a brilliant smile that warmed Jeff from the inside out. They didn’t say much else, just content to let the wind flow around them and sun beat down on their lightly tanned skin, working to make it darker.

It was the first time Jeff had ever put a concerted effort into learning how to throw a ball. Something told him, it wouldn’t be the last.


Saturday, July 14

Jeff blinked awake at the sound of an endless banging on his door. He squinted over at his clock and groaned. It was only 9:30. Who the hell was knocking on his door at 9:30 on a Saturday?

He groaned and dragged himself out of bed, grabbing a pair of sweats from his hamper and pulling them on before achingly making his way out to the living area. He inwardly cursed his body for the aches and pains, reminding him endlessly that he wasn’t such a young man anymore; although if 40 was the new 30, then 34 had to be the new 24, right? But then that would make 21 the new 11, and that was just something he didn’t want to get into... especially when he pulled open the door.

“What are you doing here?” he asked, peering out at the woman on the other side. Annie stepped past him, a cheerful smile on her face and a tote bag on her arm.

“Get dressed, we’re going out,” she demanded. Jeff groaned and shut the door.

“But it’s 9:30.”


“It’s 9:30 on Saturday. Bed,” he pointed pathetically toward his bedroom. “I wanna be in it.” Annie rolled her eyes.

“Stop whining. Come on, this’ll be fun!” He gave her a dirty look for the ‘whining’ comment.

“What is this exactly?” He crossed his arms, waiting impatiently for her explanation.

“We’re going on a little road trip.” His brow creased.

“A road trip.”

“Yes! So go get dressed and we’ll go!” she exclaimed. “And pack a bathing suit and towel.”

“Why me?” he whined again.

“Because you need to do more fun things.” He gave her a pointed look. “AndIWasHopingToTakeYourLexus,” she added quickly.

“Aha,” he said with a small smirk.

“C’mon, Jeff,” she attempted. “The open road, tunes, wind blowing in your hair, salty road food...”

“No to the salty road food,” he said firmly.

“Okay, healthy road food,” she bargained.

“It’s not the type of food that I’m concerned about, it’s the food in general. You should know by now that no food enters the Lexus... besides, there’s no such thing as healthy road food.”

“Carrot sticks!” she supplied.

“Okay, there’s one.”

“Snap peas, celery sticks, apple slices...” Jeff shook his head at her and wandered away as she continued her list.

He returned a few moments later dressed and with his shades on his head, bathing suit and towel in hand.

“You got any room in that tote bag?” he asked. Her face opened up with a wide grin and she opened her bag for him, allowing him to stuff his belongings inside before the two headed out.


“So where exactly are we going?” Jeff asked once they were on the road.

“It’s a surprise,” Annie said cryptically.

“But I’m driving,” he argued. She shrugged.

“I’ll tell you where to go.” He sighed deeply and opted to let it go. He knew once Annie had a plan in place, it was pointless to try and sway her. He turned up the volume on the old rock station blaring from his radio and the two raced down the highway, singing badly along with Lyndard Skynard.

They drove for nearly an hour and a half before Annie directed him to an exit, and then another twenty minutes before he was told to take another street. He frowned when the street was unpaved, clearly more concerned about the well-being of his tires and paint job than the opportunity for adventure.

But eventually they did arrive. Annie jumped out first once the car was in park, running forward slightly and through to a clearing where the road ended. Jeff killed the engine and followed her out.

“What do you think?” she asked, gesturing out to the space before them. Jeff took in the scene: incredible cliffs about twenty feet above a lake filled with the clearest water he’d ever seen. From what he could tell, there were easily navigable foothills heading up the sides that they would be able to take up and down. Beneath the clear, cloudless blue of the sky, Jeff had to admit that this was one of the most beautiful places he’d ever seen.

“Okay, this was worth getting up at 9:30,” he admitted. Annie smiled widely up at him and reached down to the hem of her sundress, pulling it over her head. Jeff didn’t even bother trying to hide his leer as she did so. He’d seen Annie in a bathing suit before, but the experience never got old. One she was undressed, Jeff jogged back to the car to put on his own swimsuit.

Once dressed, he rejoined her where she’d come to sit at the edge of the cliff, feet dangling over.

“No fear of heights here, huh?” he asked, standing back a little.

“Naw, no point,” Annie said, swaying her feet over the twenty-foot gap.

“Well, there is some point,” Jeff argued. “You could always fall and die.” Annie peered back at him, noticing his distance.

“Jeff, are you afraid of heights?” she teased.

“Pfft. No,” he scoffed. “I’m just a realistic, rational person who doesn’t go near dangerous ledges.” Annie laughed out loud at this and shuffled herself a little closer to the edge. “What are you doing?!” he exclaimed.

“I think I’m gonna jump,” Annie said, a wicked smile on her face. Jeff’s eyes widened.

“Are you sure that’s safe?”

“Of course it’s safe. We’re not even that far up.” Jeff looked at her incredulously.

“It’s like 50 feet!” he exclaimed. Annie rolled her eyes and got to her feet, standing at the edge.

“It’s only 20 feet. Don’t be dramatic,” she said. She peered over and Jeff felt his stomach lurch.

“Seriously, can we just walk down?” She shrugged.

“You can.” He groaned.

“Annie, I’m serious, this is way too high.” She peered over her shoulder.

“Then walk down, Jeff. You can meet me there.” She shuffled forward a little more.

“Is this going to take a dark turn?” Jeff asked, his heart now firmly implanted in his throat. Annie scoffed at him.

“Count me down!” exclaimed.

“No!” Jeff protested.

“Come on, Jeff.”

“No way,” he said firmly. She rolled her eyes and took a few steps back from the edge. Jeff sighed in relief. “Thank God,” he muttered.

And then Annie was running full-tilt toward the edge, flinging herself over it. The air was cut with an ear-piercing scream as she fell. Jeff raced to the edge, his heart hammering painfully in his chest as he saw the giant splash beneath him. He waited with baited breath for five, ten, fifteen seconds, his entire body shivering.

And then she resurfaced, first with a gasp of air, and then a loud, almost hysterical laugh that reached his ears just before he lost all composure.

“Are you freaking insane?!” Jeff called over the edge. Annie peered up at him, treading in the deep water, a wide smile on her face.

“Jeff, that was amazing!” she yelled back. “You have to do it!”

“What? No way!” he called back.

“Come on, Jeff. Don’t be a chicken.”

“It is not chicken to not want die, Annie,” he bit back. Annie’s laughter filled his ears once again and he watched her swim around a little bit. She didn’t look broken, bruised or battered. She didn’t even look sore from what had to be a painful landing, she just looked... happy. Thrilled, even. Like she’d accomplished something.

“You know you want to,” her voice reached his ears, a little quieter this time. He looked over the edge again, his heart thumping incessantly, his ears ringing with adrenaline. Holy crap. He was going to do this. He was going to jump off a cliff... what the hell?

He backed up and tried to steady his breathing. He took a good ten seconds to do so, and offered a prayer of, “God, I don’t know if you exist, but please don’t let me die,” before setting himself into motion and carelessly flinging himself over the edge.

He wasn’t sure if the high-pitched scream he heard was emanating from his own throat, but it was a little embarrassing. That was his last thought before he hit the water and descended a good ten feet below the surface. He swung his arms and legs rapidly, trying to reach the bright surface as quickly as possible in search of that ever-elusive oxygen. When finally he surfaced, he gasped for air, his lungs clamoring for every breath.

And then his heart settled down, and his breathing slowed, and he came to the slow realization that he was still alive. He had jumped off a cliff, and lived to tell about it.

He felt Annie’s arms wrap around his neck before he realized she was in front of him.

“I’m proud of you,” she whispered in his ear. He grinned and wrapped his arms around her, the two treading water out in the middle of the tiny sanctuary Annie had brought them to.

Yea, he was pretty damn proud of himself, too.


Sunday, July 29

“I can’t believe I let you talk me into this,” Jeff grumbled as he parked the car along the side of the road. There were about six other cars there too, and a group gathering at the mouth of the trail just up ahead.

“You’re going to have a blast,” she reassured him for the hundredth time. “Besides, it’s for a good cause.”

“Is that cause the “Annie Makes Jeff Do Awful Stuff Foundation?” Because I’m thinking of pulling my support.” Annie unbuckled herself and turned in her seat toward him.

“You know it’s Big Brothers Big Sisters. Those kids,” she said, pointing to the group, “need mentors. A lot of them come from single parent families in rough neighbourhoods, and it’s the least we can do to take them out for a hike.” Jeff rolled his eyes.

“I had a single parent household—no one took me for a hike, and I turned out fine.” Annie fixed him with a glare. “Mostly fine,” he amended. Annie grabbed his hand and gave it a little squeeze.

“Just try to have a good time, Jeff. This is going to be fun.” He sighed deeply.

“Fine. But if this turns out to be the disaster I think it’s going to be, you owe me. You owe me big time, sister.” Annie giggled and leaned forward, placing a chaste kiss on his cheek.

“Thanks Jeff. Let’s go!” Jeff waited a moment as she extracted herself from the car before following, gathering his wits. Spending a day hiking in the woods was one thing. Spending a day hiking in the woods with 12 hyper kids and teenagers was another entirely.

Again, he had no idea how he let Annie convince him to go with her on this one.


The hike started not long after Annie and Jeff joined the group. Every adult was assigned three kids to keep watch over as they embarked on the four mile journey. Jeff’s kids were Jacob, Kyle and Lisa. He knew who Lisa was; it was a toss-up as to which was Jacob and which was Kyle.

As expected, he was extremely awkward with all three of them when they started. He didn’t know how to talk to kids, or act around them, or what to do to keep them entertained. He settled for walking a few steps behind them to make sure they were all still with the group. He figured keeping them from getting lost was probably his primary function anyway.

The first mile passed by like this, just walking, with Lisa and one of the boys (Jacob, maybe?) talking amongst themselves while Kyle wandered a little further away from them, his hands in his pockets, his head down. Jeff frowned at the boy, wanting to help make this a more enjoyable experience for him, but not knowing exactly how to do that.

He peered further ahead at Annie. She had three girls, and all three of them were excitedly talking her ears off. One of them was even holding her hand and peering up at her like she was totally amazing. Jeff smiled a little at that. He could relate—he spent a lot of time staring at Annie and thinking she was totally amazing too. He looked over at Lisa and Jacob. They were getting along great. They didn’t even need him. He thought he smelled puppy love, which kind of warmed the cold, dead cockles of his heart, just a little.

But then a quick glance back to Kyle told him this still wasn’t going as well as it should have been. He picked up his pace, stepping into stride with the boy who only came up to Jeff’s shoulder.

“So, Kyle,” Jeff started. 

“It’s Jacob,” he corrected quietly. Jeff groaned inwardly.

“Right, sorry. Jacob,” he said again. “What’s your story?” he winced at his own insensitivity. He was so not good at this. Jacob just shrugged and said nothing, keeping his head down. “Well... how old are you?” he attempted again.

“Fourteen,” Jacob said. Jeff nodded.

“Fourteen, huh? Got a girlfriend?”


“A... boyfriend?” Jeff attempted. He inwardly kicked himself when the kid looked up at him, a little confused

“What are you doing?” Jacob asked. Jeff’s brow furrowed.

“What do you mean?”

“Why are you trying to talk to me?” he clarified. Jeff shrugged.

“I dunno. I’m your leader... that’s what leaders do.” Or at least he thought that’s what leaders did... he wasn’t 100% sure.

“Not here,” Jacob clarified. “I’ve been on six of these hikes... no one’s ever said anything.” Jeff frowned.

“Well... that’s stupid.” Jacob shrugged.

“I guess.” Jeff bit his lip, not sure what else to say, but kind of relieved that the kid was actually talking to him.

“So you’re on the waitlist?” he asked. Jacob looked up at him. “For a Big Brother,” he clarified.

“Yea, I guess.”

“How long have you been waiting?” Jeff asked. Jacob shrugged.

“Two years, maybe? I don’t really know. My mom signed me up.” Jeff was a little surprised by this.

“Why so long?”

“I dunno. They matched me once by the guy didn’t stick around. Said we were incompatible,” he explained. Jeff rolled his eyes. What a jerk.

“So what now? You just go on a lot of hikes, huh?” Jacob laughed lightly. It was the first time Jeff had seen the kid crack a smile. He felt a small amount of pride for that.

“Yea, a lot,” Jacob said. He turned to look at Jeff. “My mom likes to have me out on these things.”

“Why’s that?”

“I don’t know. Probably because she feels better when I’m not at home.” Jeff’s brow furrowed. Jacob explained: “We live in a pretty shitty part of town. It’s not really safe.” Jeff nodded slowly.

“What about your dad?” he asked. “What does he think about all of this?” Jacob huffed.

“You’d have to find him and ask him yourself. I haven’t seen the guy since I was five.” Jeff frowned. Now he knew why he was so drawn to this kid—he was him.

“I haven’t seen my dad since I was a kid either,” Jeff informed him. Jacob’s eyes shot up, surprised.


“Yea,” Jeff confirmed. “He was just there one day, and gone the next.” Jacob nodded slowly as he digested this new information.

“So you kind of... know what it’s like then,” he said slowly. Jeff offered a sympathetic smile and clapped Jacob on the shoulder.

“I know all too well, Buddy. But you know, it gets better. After a while you stop worrying about what he’s doing, and start worrying about what you’re doing—where your life is going.” Jacob nodded slowly.

“Like you’re finally free of him?”

“Exactly,” Jeff agreed. Jacob offered him a lopsided smile.

“Thanks for talking to me, Jeff.” Jeff grinned down at him.

“Thanks for letting me, Jacob.”


As Jeff and Annie pulled away from the roadside where his car was parked, Annie turned toward him in her seat, a smile on her lips.

“So how was it?” she asked, excitedly. Jeff offered a small smile.

“It was good,” he said. “Really good, actually.” She grinned.

“Oh, I’m so glad!”

“Yea,” Jeff agreed. He peered over at her for a second before returning his eyes to the road. “Hey, do you know anything about becoming a Big Brother?”


Thursday, August 16

Jeff and Annie walked through the central part of Greendale. It was now mid-August, and the weather was hotter than ever. Annie was dressed in her typical sundress, although this one had slimmer straps and was shorter than most. Jeff had given up on his designer jeans and turned them in for a pair of khaki shorts and a tight white v-neck t-shirt. He still looked like a Gap ad, but now he featured their summer collection.

This was probably the tenth or fifteenth time the pair had taken off together for one of their much-loved days off from Greendale. The rest of the group didn’t seem fazed by their sudden closeness, which Jeff took as a blessing. He wasn’t interested in answering questions about whatever it was he had going on with Annie. He wasn’t even sure there was anything going on with Annie. Sure, they spent a lot of time together, and occasionally, like at this particular moment, they held hands... but they never went further than that. There was no kissing, no heated lovemaking on humid nights, no candlelit dinners (or, well... no romantic candlelit dinners), no frantic hands or hushed moans... there was just time. Lots and lots of time spent together, doing everything and nothing.

And so today it seemed perfectly natural that they would, together, head downtown to enjoy the Busker Festival. Each year in August a group of street performers made their way to the middle of downtown Greendale and performed. They were flanked by small shops selling things made by local artisans, trucks selling greasy food, and lots of other fun, interesting things that one could only find during a one-week period in the middle of the summer. It was one of Annie’s favourite times of year—a fact she had made clear to Jeff when she was begging him to join her the night before.

The two wound through crowds of people surrounding various acts. One man was break dancing, another was throwing knives, a woman was doing contortion and another was doing acrobatics on stilts. It was all very bizarre, but undeniably entertaining. Annie stepped forward in one crowd to watch a man play a complicated concerto on the cello. Jeff stepped up behind her, wrapping his arms around her middle and allowing her to rest against him. He could have argued away their proximity as being due to the large crowd around them, but if he was being honest, he just liked having her near him.

“He’s incredible,” Annie said, her head craned so she could see him. Jeff just smiled down at her, placing a quick kiss on her cheek. He saw her smile before she turned her head back to watch the performer finish the song.

They moved on after that, visiting various pup tents and looking at what the artisans had to offer. There were seas of homemade jewelry, of which Annie picked up two or three bracelets and necklaces. Jeff plucked a purple geranium from one vendor while Annie had her back turned and presented it to her as she swung back around, tucking it into her hair behind her ear. He was met with a smile that was well worth the $2.95 the flower had cost.

As they ventured further, they passed by a tent where a few guys were applying airbrushed tattoos to customers. Annie pulled Jeff to a stop and pointed excitedly.

“We should get tattoos!” she exclaimed. Jeff chuckled.

“You a badass now?” She rolled her eyes.

“Tattoos aren’t just for badasses, Jeff. They’re a way of expressing your individuality.” He huffed.

“Yea. I can’t tell you how many women I’ve slept with who expressed their individuality with butterfly tramp stamps.” Annie made a face.

“One, gross, and two, it could be worse. They could have gotten your name tattooed on them. Then they really would have looked like idiots.”

“Ouch,” he joked, putting a hand over his heart. Annie giggled and pulled him toward the tent. “Oh wow, you’re serious about this.”

“Duh doy,” Annie said. Jeff winced at the use of Britta’s favourite nonsense term. “Come on, Jeff. Live dangerously!”

“It’s not really dangerous to get a fake tattoo that only lasts a week, Annie.”

“Oh, I’m sorry, did you want to get real tattoos? I’m sure there’s a parlor open around here somewhere,” she teased. Jeff rolled his eyes.

“You have at it. I’ll just stand back and watch you mutate.” She pouted a little.

“Come on, Jeff. It’ll be so much more fun if we get them together. Oh! We can get matching ones and be like bosom buddies!” she exclaimed. Jeff shook his head.

“Nuh uh. I don’t do bosom buddies unless I actually get to enjoy the... bosoms.” Annie scoffed and wrapped her arms over her chest.

“Pig,” she said, although she had a small grin on her face that belied her disgust. Jeff smirked.

“But hey, if we can somehow work the bosoms in though, I might be swayed.” She giggled lightly and dropped her arms to just under her breasts, pushing them up a little and laughing at the way Jeff groaned.

“That enough bosom for you?” she asked. Jeff shook his head.

“Not by a long shot.” She just giggled and dropped her arms.

“Well that’s all you get... unless you get a tattoo with me.” She slid into the seat next to the artist and pointed to the picture she wanted. As he searched through his pack of stencils, she looked back up at Jeff, waiting patiently for a response.

“So... wait... do you mean I get more boobs if I get one of these stupid things?” he asked. “How much boobage are we talking about here?” Annie giggled and put her arm out for the man to start stenciling.

“Oh, I don’t know. Are you a gambling man, Jeff Winger?” she asked, a flirty grin thrown over her shoulder at him. He contemplated this.

“Depends on the odds.” She grinned.

“Well, the odds are in your favour... IF you get a tattoo, and IF you let me pick it.” Jeff’s eyes widened.

“That wasn’t in the original deal.” She shrugged her free shoulder.

“I just added it. I can do that, because I have the boobs.” Jeff’s eyes narrowed.

“You’re becoming dangerous, Annie.” She giggled.

“Is that a yes?” she asked. Jeff hesitated a moment before nodding.

“I can’t believe I’m doing this. Yes,” he said with finality. He slipped into the seat next to the other artist. “What’s the damage?” he asked. Annie motioned for the artist to come over to her, and whispered something in her ear. “Seriously? You’re not even going to tell me?”

“It’s an even cooler surprise,” Annie said with a giggle. Jeff frowned.

“Somehow I doubt that.” He pushed his sleeve up and looked away as the artist placed the stencil against his arm and began airbrushing black ink over it.

A few minutes later, both of them were done.

“I’m afraid to look,” Jeff groaned. Annie giggled and peered down at her arm and moved so Jeff could see it. He smiled lightly. “Wings, huh?” She grinned and nodded.

“Now look at yours.” He looked down at his arm and his brow creased.

“A light bulb?” he asked. He looked up at her for clarification. She grinned.

“Invented by Edison,” she explained. A small grin spread across Jeff’s face.

“You’re even a nerd when it comes to tattoos,” he teased. Annie giggled. “Okay, we had a deal,” he said, pointing to her boobs. Annie laughed lightly and grabbed his hand, pulling him along with her away from the tents and vendors. Jeff let her pull him along, but was starting to feel a little uneasy about the whole thing.

“Okay,” she said once they were hidden from view. “You get one flash—if you don’t get a good enough look, that’s your problem.” Jeff shook his head.

“I was kidding about the boob thing, Annie. You don’t owe me anything.” She raised an eyebrow.

“You sure?” he nodded.

“I’m sure.” She smiled and fingered the top of her sundress. “Annie...”

“What?” she asked.

“Annie, you don’t have to.” She shrugged and pulled it away from her body a little, peering down.

“I don’t know. They’re pretty spectacular—you sure you don’t want a peek?” she teased. Jeff groaned.

“You’re the worst, you know that?” She giggled and let the top snap back in place.

“I know. You’re just too easy.”


Monday, August 27

It was the end of August and classes were over, giving the group a one week reprieve before the fall semester started up. Jeff took that time to continue to look desperately for a job that would keep him housed and fed for the next year.

He was currently sitting in the offices of a small local start-up that Annie had shown to him in the classified ads (yes, the actual newspaper classified ads). The new firm was run by some notable lawyers; notable enough that Jeff had heard of them, and had even defended against one of them years earlier. He was nervous sitting before the two partners, feeling scrutinized and believing fully that they would send him away empty handed once again.

“Mr. Winger, your record speaks for itself,” said one of the partners, peering down at his rap sheet. He shifted uncomfortably in his chair.

“I know it looks bad, but I’ve done a lot to turn that around in recent years,” he attempted meekly. The man peered over the edge of the sheet.

“I’m not talking about that record. I’m talking about your caseload. You’ve got a pretty impressive list of improbable wins here.” Jeff sat up a little straighter, surprised.

“Oh, yea. They used to call me a litterbug because I put so much trash back out on the street,” he joked. The other two men in the room laughed along with him. Leave it up to lawyers to find that funny and not just gross.

“I remember you,” said the other man, pointing at Jeff. “You were a spitfire in the courtroom.” Jeff smiled.

“Thank you sir. It was a tough battle.”

“A battle you won,” he clarified. Jeff nodded slowly.

“Yes sir.”

“Jeff, call me George,” the man corrected. The other man jumped in.

“And call me your boss. That is, if you’ll accept a position with Schuester & Simon,” he said. Jeff looked at them incredulously.

Really?” he asked.

“Of course, it will only be on a contract basis until you finish your bachelor degree.”

“Of course!” Jeff said enthusiastically.

“Great! So we’ll see you next Monday?” asked George. Jeff grinned widely and stood up, reaching forward to shake their hands.

“Monday it is,” he said excitedly. “Thank you George, Mr. Simon... you won’t regret this, I promise.”


Back in his car, Jeff was nearly vibrating out of his seat. How was it possible that after so many interviews and so many horrible let downs, it took a guy he had absolutely obliterated in the courtroom to give him a job.

He had to tell someone. He was too excited to keep this in. He reached over to his hands-free device and punched in a number by heart, before putting the car into gear and pulling away from the curb.


“Annie, it’s Jeff,” he said, as though he still needed to announce himself.

“Hey! What’s up?” Jeff could hear a commotion in the background.

“What’s going on over there?”

“Oh, Troy and Abed are having a waterless water balloon fight.”

“... I don’t get it.”

“Neither do I. Suffice it to say, THEY ARE GOING TO BE CLEANING THIS UP,” she thankfully screamed the last part away from the telephone receiver. Jeff just chuckled.

“Okay, it sounds like you need an escape route... you interested in coming over for dinner tonight? I have some news.”

“Dinner?” her voice squeaked a little.

“Yea, at my place.”

“You mean like just us? Or should I ask Beavis and Butthead to come too?”

“No, just us this time. Cool?” There was a moment of silence on the line.

“...okay. What time?”

“7:30?” he asked.

“Okay. I’ll see you then.”

“Oh!” Jeff remembered. “Annie, dress nice, okay?”

“Dress nice?”


“For dinner at your apartment?”

“Yea!” Jeff said again. He heard her laugh lightly on the other end and smile.

“Allllllright,” she drawled. “I’ll see you at 7:30 in my Sunday best.” Jeff chuckled.

“Well, I hope not your Sunday best.” He could hear her scoff on the other end.


“Yea, but you like me that way.”

“Goodbye, Jeffery.” Jeff chuckled.

“See you later, Annie.”


Around 6 o’clock that evening, Jeff skittered around his apartment, putting dinner in the oven and tidying up as much as he could. He knew Annie had seen his apartment in all states, especially over the past several months, what with her penchant for dropping by unannounced, but he really wanted this to be something special. He had gotten a job—a job that she had made him aware of. As far as he was concerned, that was a win on both of their parts, and he was fully intending to celebrate that win to the hilt with her that evening.

And yea, maybe he had some ulterior motives too. Maybe.

But mostly he was just eager to see her face light up when he gave her the news. Maybe she would give him a huge hug and offer endless words of encouragement about how she knew he could do it. Maybe she would throw caution to the wind and just kiss him already. Maybe she would do that adorable little bouncy thing she did when she got excited.

Or maybe she would just beam up at him, and the warmth of her smile would be enough to make him weak in the knees all over again.

Whatever she did, he knew it would be the absolute perfect reaction. Annie was good at getting things right. Hell, she had even predicted months earlier that things would work out for Jeff, at a point when he wasn’t so sure of that himself. She’d been so ceaselessly supportive of him all summer, not just as he made his way through the aggravating world of job applications and interviews, but also during their little adventures. She pushed him to do crazy things, like cliff diving, learning to throw a baseball, getting temporary tattoos, eating carbs in the afternoon and going on a hike with a dozen kids (Jacob was now his official Little Brother—something Jeff never would have anticipated, but he was more excited than ever about having that kind of bond with someone).

She’d pushed him hard, and he’d come out of it, he thought, a better man.

And that’s what this dinner was really celebrating. He was a man who had faced and overcome his fears that summer. He’d overcome obstacles that had been in his way his entire life, and he never could have done that without her help. Sure, throwing a baseball might have seemed silly and unimportant to most, but his inability to do so had always taunted Jeff. The same could be said for his fear of heights. He’d always stayed back from the ledge, both literally and metaphorically. Annie pushed him over, and he lived to tell the tale. He was ready now to take one more leap for Annie. One more leap that was a long time coming, but if she would have him, he knew it would be his most impressive one yet.

So as the chicken was cooking and the pasta was boiling, Jeff pulled on one of his nicest suits and ties, his buffed black shoes, styled his hair just-so, and broke out his most expensive bottle of champagne, setting it in a bucket of ice on the counter so it would be sufficiently cooled when she arrived. He set the table using all of the proper fork/knife/spoon regulations, and set tall champagne flutes along with each place setting, with a pair of tall candles in the centre.

And then when dinner was prepared he set it in the oven to keep it warm, lit the candles, and began pacing nervously, waiting for Annie to finally knock on his door.

Which she did, at 7:30 sharp.

Jeff’s breath left him in a whoosh when he opened the door and saw Annie for the first time. She was wearing a royal blue dress with spaghetti straps that hit about mid thigh and a pair of tall black pumps that made her legs look seven miles long. Her hair was slightly curled and spilled over her shoulders, contrasting the dark chestnut strands with the slightly tanned skin that could be found there. Everything was so simple and elegant, and yet so incredibly beautiful. Jeff honestly wasn’t sure what to say or do next.

“Hey,” she said a little breathlessly. It was then that Jeff realized she was also giving him the once-over. It made him swell a little with pride.

“You look gorgeous,” he said quickly, before his brain could clamp down on that thought. She beamed up at him.

“You look pretty good yourself, Mr. Winger.” Jeff grinned and stepped aside, allowing her to enter. He couldn’t see her face, but he heard her gasp as she took in the scene he had set, with just flickering candlelight brightening the centrepiece for the room. She swung around to face him, a look of awe on her features.

“You did all this?” she asked. Jeff offered a slightly bashful shrug.

“Yea,” he said meekly. She cocked her head to the side.

“What’s the occasion?” He smiled lightly and stepped forward, surprising her by putting his hands on her hips.

“Well, there are a couple reasons,” he stated slowly. She peered up at him from underneath her eyelashes, obviously waiting for his explanation. Her hands came to rest on his biceps, which he wasn’t about to complain over. “The first reason, is to say thank you.” Her brow furrowed.

“Thank me? For what?”

“For having faith in me this summer. Your support has really helped me through this whole job thing. I couldn’t have gotten through it without you.” She shook her head.

“Jeff, you can do anything you set your mind to, you know that.” He shook his head.

“Not this. When you found me on that park bench back in June, I was ready to give up. You didn’t let that happen.” Annie bit her lip, but nodded slowly.

“Okay... what else?”

“Well,” Jeff said slowly. “It’s also a little celebration, of our summer of adventures,” he explained. Annie grinned widely.

“You mean all of those adventures I had to drag you kicking and screaming to do?” He chuckled.

“Yes, all of those ones.” She giggled.

“Okay, that’s a good one. Is that it?” Jeff shook his head.

“Nope, there’s one more thing.” She raised an eyebrow, waiting for him to continue. “Tonight, we’re celebrating my official employment with Schuester & Simon, a job I wouldn’t even know about if not for you.” Annie’s eyes widened and she stepped back, a little bounce in her step.

“You got the job!?” she exclaimed. Jeff laughed.

“I got the job.” She bounced a few more times.

“YOU GOT THE JOB!” She raced forward and wrapped her arms tightly around his neck, a feat made easier by her four-inch heels. Jeff laughed joyously and wrapped his arms around her, picking her up. She swung her feet up and they both laughed at the sound of her shoes hitting the floor.

Carefully, after a moment, Jeff set her down (allllll the way down) onto her bare feet, but continued to hold her tightly to him.

“I couldn’t have done this without you Annie. You’ve been so amazing to me all summer.” She beamed up at him, her hands playing with the hair at the nape of his neck.

“You did this yourself, Jeff. You deserve it.” He smiled down at her, his hands splayed across her lower back as the two just watched each other for a moment. All summer they’d been leading to this, with stolen glances, hands held, days shared and nights spent anticipating their next moments together. Jeff knew he had to do it. It was the only fitting way to cap off the summer of “Jeff and Annie.”

“Would you be totally freaked out if I kissed you right now?” His voice was a little weaker than he’d hoped for, but he felt a flood of relief when Annie bit her lip to quell her grin.

“I’d be pretty disappointed if you didn’t,” she answered honestly. Jeff smiled broadly and leaned down, capturing her lips in a soft, searching kiss. It had been such a long time coming that he was impressed with his own restraint.

It lasted only a moment before Annie’s gurgling stomach interrupted them. They both broke away laughing.

“I should probably feed you, huh?”

“Yes!” she exclaimed, an incredible smile on her face. Jeff led her to the table and got her situated before serving dinner.

Of all of her possible reactions, he never expected that he would get all three.


Dinner passed like all of the other times they’d spent together that summer. The conversation was easy and enjoyable, and Jeff could hardly believe how comfortable they both were in this new space their relationship seemed to occupy. No words had been said to solidify what they both knew to be true, but it seemed at that moment that words were the last thing they needed. Their relationship was all talked out. It was time for action, and he knew it.

And so when dinner was over, he and Annie retired to the couch, where cheerful conversation gave way to stolen kisses in the dimly candlelit room, with hands roaming freely over all of the places they’d each dreamed of for months. Jeff shifted them so he was laying on his back with Annie splayed out on top of him, both of their nice clothes becoming wrinkled between bodies in search of touches, friction, ecstasy, everything. It was only when Annie began unbuttoning his shirt that he realized he didn’t want to do this on the couch that Chang had called home for months.

“Annie,” he said in between heated kisses. She dipped her mouth to his neck. “Annie,” he tried again, pushing her up slightly. She backed away, looking down at him with her swollen red lips parted, her sweet breath falling across his face as she lightly panted.

“Don’t stop,” she whispered quietly, a hint of uncertainty clear in her eyes. Jeff reached up to tangle his hand in her hair, bringing her lips back to his for a quick peck.

“Never,” he mumbled against her lips before creating space again. “Let’s just change up the locale, okay?” She peeked behind her at his knees bent awkwardly to fit his large body to the couch and slowly, sluggishly pulled herself away. Once she was to her feet, she grabbed the hem of her dress and in a swoop, pulled it over her head. Jeff sat up and watched her unabashedly as she did so, revelling in the reveal of her deep purple bra and panty set. He put his hands on her hips and pulled her body closer to him, placing a lingering kiss on her stomach, just above her belly button. He peeked up at her.

“It’s stupid how hot you are,” he said. Annie giggled and brought her hands to his face, holding it upward so she could see him, her thumb casually sweeping over his cheekbone.

“Make love to me, Jeff,” she whispered. “I don’t to want to wait anymore.” Jeff felt a shiver at her words and raised himself to full height, shrugging off his jacket and pulling his tie off, leaving them on the couch before taking her hand and silently leading her through his apartment to his bedroom.

It was a rapid escalation once they were tangled in the sheets of his bed. The remainder of their clothes quickly found the floor as they desperately learned every inch of each others’ bodies, first with hands, then with lips and tongues. Jeff slipped into Annie soon after, finding her warm and wet and ready for him in a way he’d only dreamed of in the past. Her body wrapped around his and they moved together, finding their own rhythm. It was a slow, steady burn that matched the rhythm their relationship had taken over the course of the summer. It started tentative, and soon escalated to places that neither had expected when they began.

When they finally reached their climax, Annie once again went first, leading Jeff over the edge just as she had been doing for three months. Their bodies rocked together in time to their rapid heartbeats and intermingled gasps of pleasure and necessity as Jeff drained himself inside of her, his body becoming stiff and then slackened above her.

And then Annie just held him. She held him as she had so many times before, only without the barriers of clothes, or the pretense of friendship standing in the way of their absolute need for each other.

As they both sunk under the covers, eyes closed, limbs heavy and hearts pounding, Jeff felt himself finally and completely give over to the inevitable. The summer of Jeff and Annie was never going to be just a summer, and he had an inkling that Annie had known that simple truth all those months ago when she found him down and out on a park bench in June.

He was unsurprised to find that he didn’t care. He just wrapped her up in his arms and followed her lead once again as he fell into a dreamless sleep.