The Forgotten Gilmore

Chapter Nineteen: Rooftop Confessions

Alessia walked into Luke's and Jess's apartment above the diner without knocking, feeling at ease in the familiar space. Jess glanced up from the book he was reading, eyebrows raised but a smirk playing on his lips.

"Hey, Gilmore. Make yourself at home, why don't you?"

"Don't mind if I do," Alessia replied, tossing her bag onto a chair and plopping down on the couch. She pulled out a well-worn copy of "The Catcher in the Rye" and waved it at Jess. "Finished it."

Jess sat up, eyes gleaming with interest. "And?"

"And, Holden Caulfield needs a serious attitude adjustment, but I get it. He's relatable, in a messed-up kind of way," Alessia said, tossing the book to him.

Jess caught it and chuckled. "Welcome to the club. What's your favorite part?"

"The bit about the museum. I like how he finds comfort in things that never change, even if he doesn't admit it."

"Figures you'd latch onto that," Jess said, leaning back and lighting a cigarette. "You're more sentimental than you let on."

"Please," Alessia scoffed, snatching the cigarette from him and taking a puff. "I'm as sentimental as a rock."

They shared a laugh, the easy camaraderie evident. Jess took the cigarette back, nodding approvingly.

"Not bad, Gilmore. You've got potential."

"Potential to what? Develop a smoking habit?"

"Potential to be more than just Rory's sister," Jess said, a hint of sincerity in his voice.

Alessia rolled her eyes. "Yeah, because that's what I'm aiming for. Anyway, what's new in the world of Stars Hollow's resident bad boy?"

Jess smirked. "Not much. Just trying to avoid becoming a permanent fixture at Luke's. It's a full-time job."

Alessia laughed. "Sounds exhausting. How do you manage?"

"Lots of coffee and sarcasm," Jess replied. "Speaking of which, want to head up to the roof? It's a nice night."

"Lead the way," Alessia said, grabbing the pack of cigarettes and following him up the narrow staircase.

They stepped out onto the rooftop, the cool evening air a welcome change from the stuffy apartment. Jess leaned against the railing, lighting another cigarette and handing one to Alessia.

"So, what's the plan for tonight? Any more deep dives into classic literature?" Alessia teased.

"Maybe later," Jess replied. "For now, I'm more interested in hearing about your latest adventures in Stars Hollow."

"Adventures? Please. My life is a series of mundane events strung together by coffee breaks," Alessia said, taking a drag and coughing.

Jess laughed. "You make it sound so glamorous. Come on, there's got to be something interesting going on."

"Well, there was the great frog incident," Alessia said, smirking.

Jess groaned. "Please, I'm trying to forget detention."

"Fine, fine," Alessia said, waving a hand. "How about the time Isabella and I decided to give the town square statue a makeover?"

Jess raised an eyebrow. "Go on."

"So, Isabella and I were bored one night," Alessia began. "We decided the statue of the town founder needed a little sprucing up. We dressed him up in a feather boa and sunglasses."

Jess snickered. "That's a classic."

"Oh, it gets better," Alessia said. "The next morning, Taylor freaked out and called a town meeting to discuss the 'vandalism'. Isabella and I sat in the back, trying not to laugh while Taylor went on about respect for town history."

Jess laughed, a genuine sound that echoed in the night air. "I wish I'd seen that."

"It was glorious," Alessia said, grinning. "And the best part? No one ever suspected us. They thought it was Kirk."

Jess shook his head, still chuckling. "Poor Kirk. Always the scapegoat."

"Hey, he's got it coming most of the time," Alessia said, laughing. "But yeah, that's the kind of high-stakes excitement I'm dealing with."

"You're a real rebel, Gilmore," Jess said, smirking. "Next thing I know, you'll be organizing a town-wide prank."

"Don't give me ideas," Alessia said, playfully nudging him.

They shared another laugh, the tension between them simmering just beneath the surface. Jess took a step closer, his gaze intense.

"You know, you're not bad company," he said softly.

"Thanks, I think," Alessia replied, feeling her heart race.

Before either of them could say anything more, they heard the sound of footsteps on the stairs. They quickly put out their cigarettes and tried to look nonchalant as the door opened.

Rory and Lorelai stepped out onto the rooftop, looking surprised to see them. Earlier, Rory had been chatting with her mother about an upcoming school project and suggested they stop by Luke's for some pie. Lorelai, never one to refuse an opportunity for coffee and banter, agreed. When they arrived, Luke mentioned Jess and Alessia were upstairs, so they decided to say hi.

"Hey, what's going on up here?" Lorelai asked, her eyes narrowing suspiciously.

"Just hanging out," Jess said casually. "What's it to you?"

Lorelai rolled her eyes. "Just making sure you're not getting my daughter into trouble."

"Relax, Mom. We're just talking," Alessia said, trying to keep her cool.

Rory smiled at Jess, her eyes sparkling. "Hey, Jess."

"Hey, Rory," Jess replied, his voice softer.

Alessia watched the interaction, feeling a pang of jealousy but trying to ignore it. She knew Rory had a boyfriend, but there was something about the way Jess looked at her that made her uneasy.

"Well, don't stay out here too late," Lorelai said, giving Jess one last warning look before heading back inside.

Rory lingered for a moment, her gaze lingering on Jess. "Goodnight, Jess."

"Goodnight, Rory," Jess said, his eyes never leaving hers.

Alessia watched the exchange, feeling a mix of emotions. She knew she wasn't the only one who felt something for Jess, but she also knew she couldn't compete with Rory.

As they watched Rory disappear back inside, Jess turned to Alessia with a smirk. "Well, that was fun."

"Yeah, a real blast," Alessia replied, rolling her eyes. "Let's just get back to talking about Holden Caulfield, okay?"

Jess laughed. "You got it, Gilmore."

And so they continued their conversation, the night stretching on as they shared stories, laughs, and a growing connection that neither of them could deny.