Chapter Seventeen: A-Tisket, A-Tasket

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The Stars Hollow town square buzzed with energy as the annual picnic basket auction kicked off

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The Stars Hollow town square buzzed with energy as the annual picnic basket auction kicked off. Brightly colored blankets dotted the grass, and townsfolk milled about, eagerly eyeing the various baskets lined up for bidding. Alessia, Isabella, and Rory stood together, baskets in hand, excitement and a hint of nervousness lighting their faces.

"Okay, remind me why we're doing this again?" Alessia asked, adjusting the ribbon on her basket for the hundredth time.

"Tradition," Rory replied, giving her own basket a final check. "And it's fun. Plus, it's for a good cause."

"Yeah, and who doesn't love a little friendly competition?" Isabella added, her eyes twinkling.

Alessia rolled her eyes good-naturedly. "Right. Friendly. Sure."

As they chatted, the auction began, with Taylor Doosey serving as the lively auctioneer. The crowd cheered and laughed as baskets were presented and bids were called out.

"Next up, we have a lovely basket prepared by Rory Gilmore!" Taylor announced, holding up Rory's basket.

Dean immediately started bidding, his determination clear. Jess, standing off to the side, watched with a smirk, and then surprised everyone by entering the fray.

"Twenty dollars," Dean called out.

"Twenty-five," Jess countered, a mischievous glint in his eye.

"Thirty!" Dean quickly countered.

"Forty," Jess said without missing a beat, his eyes locked on Rory, who looked surprised but intrigued.

The bidding war continued, the price climbing higher with each exchange. Finally, with a dramatic flair, Jess made the winning bid. "One hundred dollars."

The crowd gasped, and Dean's face fell as Taylor declared, "Sold! To Jess Mariano!"

As Jess sauntered over to collect Rory's basket, Taylor muttered into the microphone, "Never thought I'd see the day a hoodlum like Jess Mariano would outbid the fine young man Dean."

Jess ignored the comment and approached Rory with a smug grin. "Looks like I'll be having lunch with you, Gilmore."

Rory managed a small smile, trying to hide her mixed feelings. "Looks that way."

Alessia watched the interaction, her eyes narrowing slightly. As the next basket was announced—her own—she felt a knot of anxiety in her stomach.

"And now, we have a delightful basket from Alessia Gilmore!" Taylor's voice rang out.

Dean, still smarting from losing Rory's basket, jumped in immediately. "Twenty dollars."

The bidding was less intense this time, and soon enough, Dean had won Alessia's basket. He walked over with a triumphant grin, but Alessia could barely muster a polite smile.

"Guess we're lunch buddies," Dean said.

"Yeah, guess so," Alessia replied, her tone flat.

As they dispersed to their picnic spots, Rory found herself sitting with Jess under a large oak tree, spreading out a blanket and unpacking the basket's contents. Jess leaned back against the tree, watching Rory with amusement.

"So, what culinary delights have you prepared for us?" he asked.

"Nothing too fancy," Rory replied, pulling out sandwiches, fruit, and cookies. "Just the essentials."

Jess picked up a cookie, examining it. "Essentials, huh? Looks pretty good to me."

They settled into a comfortable rhythm, eating and chatting. Jess's sarcastic comments were met with Rory's quick wit, creating a lively banter that drew a few curious glances from passersby.

"So, you really wanted my basket?" Rory asked, taking a bite of her sandwich.

Jess shrugged. "Seemed like the thing to do. Plus, I figured I'd get some free food out of it."

Rory rolled her eyes. "Well, I hope it's up to your high standards."

"It's not bad," Jess said, his tone teasing. "Could use a bit more seasoning, but it'll do."

Meanwhile, Alessia and Dean sat awkwardly together, the atmosphere strained. Dean tried to make conversation, but Alessia's responses were clipped and unenthusiastic.

"Is everything okay?" Dean asked, looking genuinely concerned.

"Yeah, just peachy," Alessia replied, not meeting his eyes. In truth, she found Dean insufferably dull and couldn't understand what Rory saw in him.

As they ate in uncomfortable silence, Alessia's thoughts kept drifting back to Jess and Rory. She glanced over and saw them laughing together, a pang of something she couldn't quite identify tugging at her heart.

Back under the oak tree, the tension between Jess and Rory was palpable. They sat closer than necessary, their hands brushing occasionally as they reached for food. At one point, Jess leaned in, his voice low and teasing.

"You know, Gilmore, you're not half bad company."

Rory blushed, looking away. "Thanks, I guess."

Jess's gaze lingered on her, and for a moment, it seemed like he might kiss her. The air between them crackled with unspoken possibilities. But then, Rory pulled back slightly, a reminder of her loyalty to Dean flashing in her mind.

"I should probably get back," Rory said, her voice tinged with regret.

"Yeah, sure," Jess replied, his expression unreadable.

As they packed up their picnic, Dean and Alessia approached, the contrast in their experiences stark. Dean immediately noticed the closeness between Rory and Jess, his jaw tightening in irritation.

"Ready to go, Rory?" Dean asked, his tone sharp.

"Yeah, let's go," Rory said, avoiding Jess's gaze.

As they walked away, Jess turned to Alessia with a knowing smirk. "So, how was your picnic?"

"Thrilling," Alessia replied sarcastically. "Dean's quite the conversationalist."

Jess chuckled. "I can imagine."

The day ended with a mix of emotions, the events of the picnic leaving a lasting impact on everyone involved. Alessia's disdain for Dean grew, Rory's feelings for Jess became more complicated, and Jess's flirtatious charm continued to stir things up in Stars Hollow.

As Alessia and Jess walked back towards town, she couldn't help but feel a strange sense of camaraderie with him. Despite his rough edges and sarcastic demeanor, there was something about Jess that made her feel understood.

"See you around, Gilmore," Jess said as they reached the edge of the square.

"Yeah, see you," Alessia replied, a small smile playing on her lips.

As she headed home, Alessia couldn't shake the feeling that things were about to get a lot more interesting in Stars Hollow.

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