A Gilmore's Return

Chaoter Twenty-Three: Late Night Conversations

Alessia wrapped her arms around herself, glancing out over the water as she settled in beside Jess. For a moment, neither of them said anything; the silence was almost comforting, like a language they both understood. Finally, she spoke, her voice low but carrying easily in the quiet.

"So... Stars Hollow, huh?" Alessia tilted her head, looking at him with a half-smile. "Figured you'd still be in New York. Living it up, causing trouble."

Jess gave a faint chuckle, blowing out a thin line of smoke. "Yeah, I thought I'd be there, too. But... here I am." He shrugged, the leather of his jacket creaking slightly. "The city's great, don't get me wrong, but sometimes... sometimes you just need a break from all that noise."

Alessia nodded, her gaze drifting down the street lined with lampposts casting a warm, golden glow. "Yeah, I get that. Harvard's been... loud lately. Or maybe I've just forgotten how to turn the volume down."

Jess glanced over, catching the faint tension in her face. "You? Struggling? Come on, Gilmore," he teased, but his voice softened as he continued, "Didn't think anything could get to you. You were always the one who kept it together, even when... well, even when everything was falling apart."

A flicker of surprise crossed her face, followed by a slight, sad smile. "Guess I'm not as unbreakable as I thought. Harvard's just... intense. And sometimes it feels like I'm the one out of place there." She didn't know why she was admitting this to him, but maybe it was just easier with Jess. He had always seen through her, past her sarcasm and half-truths.

"Tell me about it." Jess's gaze turned distant, his mouth pressing into a line. "I was always the one out of place here. Guess we've both been there."

Alessia looked at him, remembering all the years he spent here, bristling against a town that never seemed to understand him. "You know, I never saw you that way. Maybe everyone else did, but... I got it. Feeling like you don't fit."

"Yeah?" He raised an eyebrow, a faint smile playing on his lips. "Maybe that's why we worked. For a while, at least."

A warmth filled her chest at that, softening the ache from earlier. Their relationship had been turbulent, filled with arguments and silences as much as laughter and whispers in the dark. But sitting here now, it was easier to remember the good moments, the times when it felt like they were the only two people who truly understood each other.

"So," she said, turning back to him with a curious look. "What exactly brings you back? I doubt you just dropped in to give Luke some company."

Jess chuckled, taking another drag before flicking the cigarette butt into a trash can a few feet away. "He called me, actually. Apparently, he's dealing with some supply issues, and he's short-staffed. And, you know, I figured it couldn't hurt to help out. He's done a lot for me."

Alessia felt a pang of something—a strange mixture of envy and admiration. Luke had always been there for Jess in a way that Lorelai... well, hadn't always been for her. "Guess that's one thing Stars Hollow's good for. People here have a way of sticking around, no matter how much you try to push them away."

Jess nodded, a slow smile tugging at his lips. "Yeah. People here, they're stubborn like that. Kind of hard to shake them."

For a while, they sat in easy conversation, memories and stories from their years apart trickling out, filling the spaces that had once been left empty. She told him about Harvard, about the late nights and the endless essays, about how every corner felt like it was pressing her to be someone bigger, smarter, more perfect. He listened, nodding, as if he could see through every word and understand exactly how she felt.

Jess shared stories from New York, too, of the people he'd met and the books he was working on, the gritty energy of the city and how it had its own way of making you feel both alive and utterly lost at the same time.

They laughed about old memories—fights over music choices, their stolen kisses under Stars Hollow's dim streetlights, arguments about books that turned into hours of discussion. And somewhere between reminiscing about the past and trading stories about their lives now, Alessia felt something within her start to ease, like a weight she hadn't even realized she'd been carrying.

Eventually, the conversation lulled, and they both sat quietly, letting the sounds of the night fill the gaps. Jess glanced over at her, something almost hesitant in his eyes.

"You know, you look... better," he said, his voice softer than usual. "More... you. Not that girl trying to please everyone else."

Alessia's heart skipped, the comment both unexpected and piercing. She looked down, a small smile playing on her lips. "Guess I finally realized it's exhausting trying to be someone else. Harvard, Lorelai, even Rory... none of that really gets me. But you... you always did."

Jess didn't respond, but the understanding was there, written in the small, unguarded look he gave her. They sat in silence for a while longer, and she found herself almost reluctant to break the moment.

When the cold finally started to creep into her bones, Alessia shivered, drawing her jacket closer. "I should probably head back," she said, a hint of reluctance in her voice.

Jess nodded, a slight smirk returning. "Yeah, don't want you catching pneumonia out here just for my sake."

As she stood up, Jess straightened too, stuffing his hands in his pockets as he looked at her. "Listen, if you ever need to escape again, I'm around. Probably helping Luke scrape by, but... I'm here."

"Thanks, Jess." She paused, then gave him a soft smile. "It's good to know some things don't change."

Without another word, she turned and walked back toward her car, feeling lighter, like the pieces of herself she'd been struggling to hold together had found a way to settle, even if just for tonight.