Imagine Book 2

Books Books Books- Jess Mariano (Gilmore Girls)

Fem Y/N

It was another dreary day in Stars Hollow, at least as far as Jess Mariano was concerned. The quirky little town, with its eccentric residents and endless supply of small-town charm, felt stifling to him. Perhaps he would run away soon, just to stir up some drama... but, for now, he leaned against the counter in Luke's Diner, flipping through a well-worn copy of Catcher in the Rye. It was his go-to for moments like this: when the diner was quiet, the town felt too loud, and he was desperate to escape, even if only into the pages of a book.

Jess wasn't expecting anything remarkable to happen that day. The morning crowd had thinned, leaving the diner with only a few regulars nursing their coffee. The sound of clinking dishes and Luke's occasional gruff mutterings formed the soundtrack of his solitude. Jess was about to retreat further into his book when the bell above the door jingled.

He looked up, more out of habit than curiosity, and there she was.

Y/N walked into the diner like she belonged, though Jess was pretty sure he hadn't seen her around before. She had an effortless air about her: confident but not ostentatious. A satchel hung at her side, and when she slipped it off, he noticed a book peeking out from the flap. Intrigued, Jess watched as she scanned the room, her gaze eventually settling on a small table in the corner. She headed there, took a seat, and pulled out her book.

Jess couldn't help but smirk. It wasn't every day someone his age came into Luke's and sat down with a book, especially not a book that looked as well-loved as hers. From his spot behind the counter, he strained to see what she was reading. It wasn't clear from the cover, but whatever it was, it was enough to completely absorb her attention.

After a few minutes of silent deliberation, Jess closed his book and slid off the stool. He didn't know what possessed him, but something about her—her quiet focus, the way she tucked her hair behind her ear as she read—made him want to strike up a conversation. He grabbed a basket of fries from the counter as a makeshift excuse and walked over.

"Hey," he said, standing by her table. She glanced up, her expression curious but not unfriendly. "What're you reading?"

She tilted the book slightly, revealing the title. Pride and Prejudice. Jess raised an eyebrow, impressed. "Not bad," he said. "Jane Austen, huh? Is it your first time, or are you one of those people who reads it every year like it's some kind of ritual?"

Her lips quirked into a smile, and Jess felt a flicker of satisfaction at having elicited it. "It's one of my favourites," she replied, her voice warm and self-assured. "I've read it a few times. What about you? You seem like the kind of guy who has strong opinions about books."

Jess chuckled, pulling out the chair across from her and sitting down without waiting for an invitation. He set the fries between them. "You could say that. I'm Jess, by the way."

"Y/N," she said, her smile lingering. Her eyes flicked to the fries, and Jess nudged the basket toward her. She took one, and he decided it was a good sign.

"So, Y/N," Jess began, leaning back slightly in his chair, "what makes Pride and Prejudice one of your favourites? Is it Mr Darcy? The witty dialogue? Or are you just a sucker for long walks in the English countryside?"

Y/N laughed, and Jess felt a strange, warm satisfaction at the sound. "It's the characters, mostly," she admitted. "Elizabeth Bennet is brilliant. She's strong and opinionated but not perfect. And, okay, maybe a little bit of it is Mr. Darcy."

Jess nodded, pretending to be thoughtful. "I get it. Brooding guy with a mysterious past. Classic move. Austen knew what she was doing."

She raised an eyebrow. "And what about you, Jess? What's your favourite book?"

He hesitated for a moment. This wasn't the kind of conversation he usually had with people. But there was something disarming about Y/N, something that made him want to share. "On the Road by Kerouac," he said. "It's... messy, but honest. It's about finding freedom, you know? Figuring out who you are."

Y/N nodded slowly, her gaze thoughtful. "I can see the appeal. It's on my to-read list."

"Well, if you ever get around to it, I'll warn you now—it's not everyone's cup of tea," Jess said, his tone teasing but genuine. "Austen and Kerouac are pretty different vibes."

"Maybe," she replied, a playful glint in her eye. "But I bet we'd find some common ground."

Jess grinned. "Oh yeah? Care to test that theory?"

For the next half hour, they did just that. They traded book recommendations, debated the merits of plot-driven versus character-driven stories, and shared their favourite lines from novels they loved. Jess found himself captivated not just by Y/N's intelligence but by the way her eyes lit up when she talked about something she was passionate about. She was sharp, quick-witted, and didn't back down from an argument—qualities Jess hadn't realized he'd been craving in a conversation partner.

As their fries dwindled, Y/N glanced at the clock on the wall and sighed. "I should get going," she said, though she didn't make a move to leave right away.

Jess felt a pang of disappointment but tried not to let it show. "Big plans?" he asked.

"Not really," she admitted, standing up and slinging her bag over her shoulder. She hesitated, then leaned down and pressed a quick kiss to his cheek. Jess froze, completely caught off guard.

"I'll come back tomorrow," Y/N said softly, her face close enough that he could see the faintest hint of a blush on her cheeks. "Same time. Maybe we can talk about more than just books."

She straightened and walked out of the diner, leaving Jess sitting there with the empty fry basket and a feeling he couldn't quite name. For the first time since he'd moved to Stars Hollow, Jess didn't feel quite so out of place.