A Thousand Tomorrows

Summary:

It's been four years since Rory left Logan on that rainy night outside her graduation party. Now, a chance encounter in New York forces them to confront their past—and their unresolved feelings.

Rory Gilmore never expected to see Logan Huntzberger again.

It wasn't that she had forgotten him—how could she? Some people leave imprints too deep to fade. But life had a way of pushing her forward, and she had let it. The campaign trail had been a whirlwind and now she was back in New York, freelancing, bouncing between deadlines and coffee shops.

She told herself she had moved on. She even believed it, until she saw him.

It was just another Tuesday afternoon. She was at the Strand, cradling a stack of books, lost in the scent of old pages, when she heard a voice behind her.

"Ace?"

Her breath caught. She turned slowly, heart pounding.

Logan stood there, hands in his coat pockets, looking every bit as devastatingly familiar as he had years ago. The same sharp jawline, the same twinkle in his hazel eyes, but there was something different, too. A weight. A hesitation.

For a long moment, neither of them spoke.

Then Rory found her voice. "Logan."

His lips curved into a half-smile. "Of all the bookstores in all the cities in all the world…"

She swallowed, tightening her grip on her books. "You're in New York?"

"Just for a few days. Meetings." He gestured vaguely. "What about you?"

"Living here now. Writing."

He nodded, as if he already knew. Maybe he did. Their worlds weren't so far apart.

She should have ended it there. She should have smiled politely, excused herself, and walked away before old wounds reopened. But she didn't. Because no matter how much time had passed, this was Logan.

And some things were unfinished.

They ended up at a coffee shop down the block, wedged into a corner booth. The air between them crackled—half nostalgia, half something more dangerous.

"So," Logan said, stirring his espresso. "Are we going to pretend that wasn't awkward as hell?"

Rory huffed a small laugh. "I thought we were doing a pretty good job."

"Right. Because running into your ex-fiancé after four years is totally casual."

She looked down at her cup. "You—uh—you look good."

"You too, Ace." His voice softened on the old nickname.

Silence stretched between them, filled with all the words they hadn't said that night in New Haven.

Finally, Logan leaned forward. "You ever think about it? About us?"

Rory inhaled sharply. "Logan—"

"Because I do," he continued, voice low but steady. "More than I should, probably."

She met his gaze. "It was the right decision."

"Was it?"

Rory hesitated. She had spent years convincing herself it was. But now, sitting across from him, she wasn't sure anymore.

Logan watched her, then exhaled, leaning back. "You know, I told myself that if I ever saw you again, I wouldn't bring it up. Wouldn't push."

"And yet, here we are," she murmured.

"Here we are," he agreed.

For the first time in years, Rory wondered if maybe, just maybe, it wasn't too late.

The coffee shop hummed with quiet conversation, but for Rory, the world had shrunk to just this booth, just this moment.

Logan Huntzberger was sitting across from her, looking at her like no time had passed at all—and yet, everything had.

She should have left by now. She should have made an excuse, avoided the what-ifs. But she didn't.

Instead, she asked, "Are you happy?"

Logan exhaled, running a hand through his hair. "Loaded question, Ace."

"You always had answers for loaded questions."

He smirked. "Not this one."

Rory let that sink in. She wanted to ask more—if he ever thought about her, if he regretted the proposal, if he was still the same Logan who once made her heart race and break all at once.

But before she could, Logan flipped the conversation.

"What about you? Living the journalist dream?"

Rory sighed. "Something like that. Freelancing. Some travel pieces, some political stuff. I'm working on a book, but it's slow."

His eyebrows lifted. "A book? That's incredible."

She shrugged. "It's terrifying."

"You? Terrified?" Logan grinned. "Come on, Ace, I've seen you stand up to Mitchum Huntzberger."

Rory laughed softly. "That was different. That was me being young and idealistic."

"And now?"

She thought about that. "Now I'm older and… still figuring it out."

Logan nodded, as if he understood that more than she realized.

For a moment, neither of them spoke.

Then Logan leaned forward, fingers tracing the rim of his coffee cup. "Do you want to get out of here?"

Rory's heart skipped. "Go where?"

"I don't know. Walk. Talk. See if we still drive each other crazy." His lips quirked. "For old times' sake."

She should say no. She should end this here before she fell into something dangerous.

But instead, she said, "Okay."

And just like that, Logan Huntzberger was back in her life.

The New York streets buzzed around them as they walked, side by side, neither rushing nor hesitating.

"So," Logan said, stuffing his hands into his coat pockets, "do you hate me?"

Rory glanced at him. "For what?"

"For the way things ended."

She swallowed. "I didn't hate you, Logan."

"Past tense."

She sighed. "I was angry. Sad. But I didn't hate you. I think I hated how much I wanted to say yes."

Logan stopped walking.

Rory turned to face him.

"You wanted to say yes?" His voice was unreadable.

She hesitated. "A part of me did. But I was scared. I wasn't ready. And I couldn't be what you needed me to be."

Logan studied her for a long moment. "I never wanted you to be anything other than you, Rory."

She looked away, biting her lip. "It doesn't matter now."

"Doesn't it?"

The way he said it—soft, careful, but full of meaning—made her heart ache.

She could feel it happening. That pull, that gravitational force that had always existed between them.

It would be so easy to fall back in.

Too easy.

But before she could think too hard about it, Logan spoke again.

"Come to dinner with me."

Rory blinked. "What?"

"Just dinner." His lips twitched. "No proposals, no strings. Just two old friends catching up."

Rory searched his face.

Dinner was dangerous. Dinner meant time, memories, possibilities.

But wasn't that what she wanted? Wasn't that why she was still standing here instead of walking away?

Against her better judgment, she found herself nodding.

"Okay," she whispered.

Logan smiled. "Good."

And just like that, the door to their past cracked open again.

Rory had no idea why she was nervous.

It was just dinner. Just Logan. Just the man she had once loved—maybe still loved—sitting across from her in an intimate little corner of a candlelit restaurant in the West Village.

No big deal.

"So," Logan said, lifting his glass of bourbon, "is this the part where we awkwardly pretend this is a normal, casual dinner?"

Rory smirked, swirling the wine in her glass. "You mean it's not?"

"Well, that depends." Logan leaned in slightly, his voice low, teasing. "Are you planning on rejecting any marriage proposals tonight?"

Rory groaned, covering her face with her hands. "You are never going to let me live that down, are you?"

Logan chuckled. "Probably not."

She peeked at him through her fingers. "You're enjoying this way too much."

"Guilty as charged." He took a sip of his drink, watching her carefully. "But in all seriousness, Rory… I don't regret asking you."

Her stomach flipped. "Logan—"

"I don't," he said, cutting her off gently. "I meant it then. I still mean it now."

Rory's breath caught. "You still—"

"I still love you," he admitted, voice steady but soft.

Her heart slammed against her ribs.

Logan Huntzberger had just told her he still loved her. In a dimly lit restaurant. Over dinner. Like it was the most natural thing in the world.

And maybe, for them, it was.

Rory set her wine glass down, suddenly needing both hands free. "Logan…"

"I know," he said quickly, almost like he was trying to save her from panicking. "I know things are complicated. I know we've been apart a long time. But I also know I've never stopped thinking about you."

She swallowed hard. "Logan, I don't—"

"Have an answer?" He tilted his head. "I don't expect one. Not tonight."

She exhaled, relieved and terrified all at once.

Logan gave her a small smile. "I'm just saying… if there's even a small part of you that wonders if we could have another chance, I'd like to find out."

Rory stared at him, her mind racing.

Did she wonder?

Yes.

Did she want to find out?

Maybe.

And maybe was dangerous.

But as she looked at Logan—really looked at him—she realized something.

Maybe wasn't as terrifying as never knowing.

So instead of running, instead of overthinking, she reached across the table and took his hand.

Logan's eyes flickered with surprise, then something warmer.

"Okay," she whispered.

Logan squeezed her fingers, a slow smile spreading across his face. "Okay."

And just like that, the past wasn't the past anymore.

The night air was crisp as Rory and Logan stepped out of the restaurant, their fingers still loosely intertwined. She wasn't sure who had held on first—him or her—but neither of them seemed in a hurry to let go.

"So," Logan said as they strolled down the quiet street, "how does this work?"

Rory arched a brow. "How does what work?"

"This." He gestured between them. "Us. Do we pretend we're just old friends catching up? Do we call it a fresh start? Or do we acknowledge that we're basically two people who have been stuck in a four-year-long unresolved cliffhanger?"

Rory huffed a laugh. "You always did have a way with words."

"I do my best."

They reached a crosswalk, and Rory hesitated. Her apartment was to the left. Logan's hotel—wherever that was—was probably in the opposite direction.

This was the moment. The easy out.

She could smile, thank him for dinner, and walk away with nothing but a nostalgic memory.

Or—

"Do you want to keep walking?" she asked, surprising even herself.

Logan glanced at her, a slow smile curving his lips. "Thought you'd never ask."

So they kept going.

They ended up on the Brooklyn Bridge.

It was almost empty at this hour, just a few late-night wanderers scattered along the pedestrian walkway. The city sparkled around them, a thousand tiny lights stretching into the distance.

Rory leaned against the railing, inhaling the cool night air. "I used to love coming here when I first moved to New York."

Logan stood beside her, hands in his pockets. "Why's that?"

"It made me feel small," she admitted. "In a good way. Like no matter what was happening in my life, the city just kept going. It reminded me that nothing was permanent. Not success, not failure. Not even heartbreak."

Logan was quiet for a long moment. Then he said, "Did I break your heart, Rory?"

She turned to him, startled by the rawness in his voice.

"I—" She swallowed. "I think we broke each other's."

His jaw tightened, and he looked away, staring out at the skyline.

She could have left it there. She probably should have.

But instead, she reached for his hand again. "Logan."

He turned back to her, eyes searching.

Rory inhaled deeply. "I don't know what this is. I don't know where we go from here. But I do know I don't want to walk away from you again."

Logan studied her for a moment, then exhaled a small laugh. "Ace, you have no idea how long I've been waiting to hear you say that."

She smiled. "I think I do."

And then, as if it were the most natural thing in the world, Logan leaned in and kissed her.

It wasn't rushed or desperate. It wasn't clouded by uncertainty or hesitation.

It was slow, familiar, and full of every unspoken word they hadn't said over the years.

When they finally pulled apart, Logan rested his forehead against hers. "So, what now?"

Rory grinned. "How about we figure it out together?"

Logan chuckled. "Now that's a plan I can get behind."

And for the first time in a long time, Rory Gilmore wasn't worried about what came next.

Because whatever it was, Logan Huntzberger would be right there beside her.

One year later…

Rory Gilmore sat in her tiny Greenwich Village apartment, staring at the blinking cursor on her laptop screen.

Chapter One.

She exhaled, glancing at the stack of notes beside her—half-finished outlines, character sketches, a mess of scribbled ideas. She had spent years writing other people's stories, chasing deadlines, trying to prove herself. But this? This was different.

This was hers.

The apartment door opened, and Logan stepped in, carrying two coffees and a paper bag. "Ace, tell me you've at least written one sentence."

Rory smirked. "I wrote 'Chapter One.'"

Logan grinned, setting the coffees down. "A masterpiece in the making."

"I'm just warming up."

"Uh-huh." He handed her a coffee, then pulled a croissant from the bag and took a bite. "So, am I allowed to ask what this book is about?"

Rory hesitated, fingers hovering over the keyboard.

It was strange—she had spent months working on this, shaping it, questioning it. But now, with Logan standing in front of her, it was real.

She looked up at him. "It's about a girl who thought she had everything figured out. And a boy who made her question everything."

Logan raised an eyebrow. "Sounds familiar."

Rory smiled. "Maybe a little."

He leaned down, pressing a soft kiss to her temple. "Then it's going to be brilliant."

Rory watched as he walked into the kitchen, rummaging for plates, humming to himself like he belonged here.

Because he did.

She glanced back at the screen, fingers finally moving across the keyboard.

Chapter One: Some stories don't end. They just find new ways to begin.

She smiled to herself, took a sip of coffee, and kept writing.

The real beginning.