a/n: This is just a fun one-shot I wrote taking place at the beginning of my favorite ever Gilmore Girls episode. We all know Jess's little plan succeeds, whether or not he wants to admit it to Rory, but how exactly did he get the idea for such a thing? Your questions are about to be answered! Just a psa gg doesn't belong to me, if it did literati would have been endgame, duh. Please leave a comment and favorite or follow if you enjoy!

"I expect you all to finish the assigned reading and sum up the last of your essays we began Wednesday." The Stars Hollow High teacher's voice rang out in the small classroom. In the back row near the window with a view of the town square sat a messy-haired young man, clearly not paying attention to whatever his English teacher had to say, deeply immersed in the pages of "Raise High the Roof Beam, Carpenters & Seymour: An Introduction". His peers had simply learned to ignore his presence completely, he was absent so often no one seemed to notice his attendance regardless.

He was utterly oblivious to the noise around him, not noticing the other students' impetulant glances and eye rolls in his direction, all the talk being funneled together so they just sounded like all the adults in Charlie Brown. "Mr. Mariano!" Jess finally looked up when an angry red face landed an inch in front of his own and snatched his book from his grasp, awakening him from his deep literary trance.

"Oh, hey, didn't see you there." His signature smirk was alive and well as he leaned back in his chair, partially for show, partially to get away from the surly face with a forehead vein throbbing so hard he reckoned it might implode.

"Yes, I'm sure you haven't, considering you haven't paid in my class once for the last seven months if you even bothered to show up at all!" Obviously infuriated, the teacher's voice echoed off the walls.

"Well, now we can't have that I'll just have to take a peek at my calendar and get back to you time table-wise," Jess answered mockingly, tapping his fingers on the desk and furrowing his eyebrows for added effect. The other student's sighs were more than audible now, and a tall student with a curtain bang haircut sitting at the front of the class let out a groan before speaking up.

"Here we go again," Dean said in a loud whisper.

Laughter filled the classroom, all of them equally sick of this at least once weekly routine. Under his desk, Jess's fists clenched up but he kept his cool. "How," The teacher's booming voice asked as he glared at his most uncooperative student, "Do you ever plan to make anything of yourself if you can't even pay attention much less participate in an hour and a half long lesson?" He snapped. Jess pulled a confused expression.

"Hmmm, good question sir, I don't know how I could make anything of myself if I just didn't get that darn diploma, not like, let's see, mmm, Thomas Edison, Benjamin Franklin, Albert Einstein, Charles Dickens, Harry Houdini." He ticked off his fingers as he listed each famous high school dropout. "I just don't know what I'd do!" His teacher now resembled an overripe tomato, so infuriated he grabbed either side of Jess's desk and shoved his face right up close.

"It may not have penetrated that childish ridiculously thick skull of yours, boy, but those were still no-ti-ble persons of our society, and I will not allow you to sit here and mock their great achievements by comparing your own lack thereof henceforth do you understand?" However, there was no gratification from this speech to be found, for Jess's expression just said "make me" and before his instructor had the chance to get the final word in the bell rang signaling the end of their final class of the day.

Jess grabbed his book back and slid between the row before anyone else had even stood up. As the other students began to collect their books and bags he reached the door and the end of the first row where Dean was packing up. Jess smirked at him. "You were wrong, by the way, what you said earlier. "The Great Gatsby" was published in the spring of 25' not 23'. Maybe you should get that girlfriend of yours to tutor you on it, she didn't seem to have any problem discussing the green light symbolism with me the other day. Then again, maybe smart girls really do like em' dumb."

With that final blow, he sped off campus and back to the diner, knowing Luke would be less than pleased if he started work late especially without a solid excuse. When he reached the front he frowned at a flyer stuck to the door which proclaimed "Come one, come all, to the Stars Hollow annual Bid-a-Basket festival! Ladies bring those baskets and gentlemen, get your wallets ready because this Saturday in the town square we will be hosting the auction! Whoever bids the highest on a basket wins not whatever beautifully prepared lunch is in store but also an afternoon with the baskets original owner! All proceeds go to the Stars Hollow town fund!". At the bottom, it read "We're proud to announce this historical event will be hosted by none other than Star's Hollows very own town selectmen, Taylor Doose!" in even bigger words than the actual invitation.

Jess rolled his eyes, just great, another hockey small town "perk". He just couldn't believe that Taylor had convinced Luke to allow a flyer posted on his diner door, because unless Lorelai had made him that was completely unfathomable. To no one's surprise, Taylor and Luke were in fact having an outright spat right then and there, with Jess walking right in the middle of it. "You are such a hermit Luke, I can't believe your heart is so hard and cold you wouldn't even allow a tiny little poster for an event in a town you've lived in for your entire life! You have a duty to the people of Stars Hollow to-"

Luke cut Taylor off, coming out from behind the counter and serving his customers who were undoubtedly used to the two men's usual bickering over such matters. "To make and serve them food since that is the business I run, yes indeed, and since you are interrupting my dutiful commitment to such matters I must ask you and your flyer to leave!" Taylor was outraged by this, but opened the door and snatched the poster off.

"You never change Luke! You would steal Christmas from little Cindy Lou Who!" Luke went back behind the counter and yelled back

"If she tried to get me to hang patriarchal event flyers on my place of business I just might!" Taylor slammed the diner door and chatter rearose. When Jess slipped behind the counter and reached for the coffee pot to start his shift refilling cups Luke stopped him. "You're late! Where have you been?" He demanded, clearly not in good spirits after the blowout. Jess looked down at his watch.

"By two minutes! And mind you it was only because of the dispute I was actually here right on time." Luke frowned but dropped the topic, not in the mood to argue the point.

"Fine. I need you to go and pick up hamburger buns since my shipment got dilated and won't be in till Monday, and all any of the cholerics in this town have wanted all day was cheeseburger after cheeseburger when the entire town dies off from heart disease they won't come crying to me."

Jess resisted the urge to point out that if everyone was dead they wouldn't be able to bring their complaints to him regardless, instead just grabbing some money from the cash register and heading out again. He swore this town got more psychopathic by the hour, tons of women gathered around Dooses showing each other their baskets and ingredients they'd picked up for tomorrow. As he approached the front entrance he spotted Lorelai Gilmore conversing with Miss Patty inside and quickly made his way around back to avoid a "Hello Jess, how are you doing today?" with a cold stare, pursed lips, and raised brow. This way he might also be able to spot out the daughter of the founder of the "I Hate Jess Mariano" club without the elder Gilmores presence.

Coming in through the side door he slipped into the second aisle searching for the hamburger buns when a recognizable voice echoed from the aisle next to him. "You get no say on the basket." A girl's voice and laughter drifted over.

"I have to bid on it." Another familiar voice, but this one male and belonging to the cofounder of his club.

"And you have to eat what's inside it and you get no say on that either." He started around the corner as he heard Rory answer. As he turned around he found the culprits lip-locked at the end of the aisle by a stack of wicker baskets. He leaned against a wall of soft drinks, the crackle of a chip bag making his presence known.

They broke apart, Dean asking her "What? Taylor?" before spotting Jess standing there. His face immediately formed a look of anger and disgust, snapping "Jess." Jess pulled his favorite bored expression, perfect for all situations in which you want to annoy someone but that someone is also a good two heads taller than you so you don't want them getting so mad they crush you to a pulp.

"Sorry to intrude." He responded, voice matching expression perfectly.

"Then why did you?" Dean growled back.

"Well," he said, spotting a pack of glue sticks behind their backs and quickly thinking up a convincing story. "You were having your vertical From Here to Eternity moment right in front of the super glue."

Dean roughly grabbed a package as Rory met Jess's eye and muttered "Oh." seemingly slightly embarrassed.

"Not that it isn't an appropriate place to be doing it in front of but…" Jess started before Dean cut him off.

"Here's your glue." Said Dean, shoving the package into Jess's hand.

"Thanks, as you were," Jess said, before heading to the other side of the store to continue the hamburger bun search.

After another fruitless minute of searching, he decided to give up, and headed back to the aisle to put back the superglue, but stopped as he heard the former occupants. "I might be baking," Rory said jauntily.

"I'll pick you up at 7:00," Dean said, seemingly in a much better mood than minutes previous, that guy really could run so hot and cold on you, Jess thought with a smirk. "Get that one. It's nice and small."

She let out a small sigh before saying "Bye." Jess waited a second so he wouldn't catch them again before approaching Rory who was watching Dean head off to another part of the store. He leaned over her shoulder. "God!" She yelled, spinning around where she'd been standing.

"Sorry, two for one sale." He gave her a mischievous smile before grabbing another pack of glue sticks and heading for the checkout. A worker who thankfully was not Dean checked him out quickly and he grabbed the unnecessary packages before heading back to the diner to meet a surly disgruntled Luke since he hadn't even gotten what he'd come for and instead spent the money on unnecessary products.

But as he tried to come up with an excuse for it (the prospect of announcing his newfound fondness for scrapbooking wasn't exactly convincing), the conversation he'd overheard kept slipping through his thoughts. They'd been discussing baskets and she'd joked about baking, this must mean she was participating in that contest tomorrow. Suddenly it didn't seem so ridiculous after all. In fact, the idea hit him like a ton of bricks, nearly stopping him in his tracks as he was walking down the sidewalk.

What if he was to bid on her basket? Sure, she'd obviously been making it for her precious boyfriend but from the looks of it the baskets were simply auctioned off to the highest bidder and it was up to the guys to make sure they had enough money to win it. And if the sign was correct if he did win her basket that meant an entire afternoon with Rory, just the two of them, something that was worth all the pennies he'd spent grueling hours making at the diner. Yes, this was it, it had to be. With the next day's wonderful prospect in tow, a slightly evil grin passed Jess's face, he was ready to pull out his savings and participate in his first-ever Stars Hollow town event.