Summer was sneaking over Stars Hollow, little by little painting the town in warm golds and lush greens. Rory waddled—there was no other word for it—toward the bookstore, feeling the heat cling to her like a second skin. The temperature wasn't even that bad yet, but every movement she made and every degree the temperature climbed - it felt five times worse for her than everyone else. She was eight months pregnant, and even her go-to jersey dress barely felt decent anymore.
"Rory!" Babette commented as she passed - "You're glowing! Or sweating. It's hard to tell."
Rory laughed, fanning herself with some random leaflet she'd been handed along the way. "Definitely more of the second one," she replied, appreciatively.
She smiled as she moved along the street, catching snippets of town life. Miss Patty lounged on a bench, sipping iced tea and giving everyone who was single, or looked like it, unsolicited advice on their summer wardrobes and how to improve them with dating in mind. Some things never changed.
Life here hummed along, being all bright and vivid, but Rory felt the weight of her pregnancy more acutely with each passing day. Her feet ached, her back protested any prolonged movement, and the baby seemed determined to dance on her bladder at the most inconvenient times. To anyone who'd been pregnant in their lives, like most of Rory's female friends and family, this was no news hence Rory found mostly recognition but not a whole lot of compassion from them. Not that they didn't mean well.
Right now, however, she had every intention of spending the next couple of hours thinking about something other than her pregnancy. She was making her way toward her favorite writing spot—a small desk she'd set up by the window at her apartment, eager to do something more meaningful with her evening than she had had time for until now, visiting her mom at work.
The hardest part of starting to write again had been putting those first few words. The words had come slowly at first, halting and uncertain, but soon they began to flow. With the Stars Hollow Gazette on its annual summer hiatus - an unexpected paid perk of the job - and energy to give her book another try, Rory was allowing herself to feel a sense of cautious hope.
The second hardest part of this process had been agreeing to let Jess read her work. She'd opted for handing him chapters as soon as they were written, old-school printed pages still warm from the printer. Doing it this way spared her from dwelling too long on what she'd already put down, endlessly revising the words in a perfectionist spiral. The setup reminded her of serialized Victorian novels, where each chapter stood on its own yet built toward something greater. Jess seemed to appreciate the arrangement, though he never rushed to give her feedback. Instead, he read thoughtfully, waiting for the right moment to bring it up in conversation. He'd casually mention a phrase he found striking, or linger on a scene that felt particularly vivid, offering just enough insight to keep her momentum going without overwhelming her.
One afternoon, she handed him her latest chapter over some chilled fresh lemonade at Luke's. "Here you go," she said, sliding the pages across the table. "Your weekly installment."
Jess took the pages, smirking. "Do I get a subscription discount?"
"Just read," Rory said, rolling her eyes but smiling. She felt incredibly relieved that they'd been able to push their dangerous situation back in Boston to the back of their mind and just stayed friends. Thinking back she was grateful for Jess having turned her down., despite still feeling a hint of embarrassment. But blaming her hormones had become second nature by now. Perhaps that was just an excuse of poor judgement, but at least she had that option right now.
As if it was no big deal, Jess put the pages into his messenger bag, and they focused their attention on Jess' own book that was beginning to be in its final form. Oddly enough, on some days, he seemed less enthusiastic about it than she did. But she knew how to push him to polish it to be the best she believed it could be.
Later that evening, Jess sat in his study, Rory's latest pages spread out on the desk before him. From the adjacent living room, the sounds of Moana drifted in through the open double doors, along with occasional bursts of laughter. Rory had made a habit of hanging out with them—just for fun, blending her editing work with the easy companionship of friends and lending a hand with things Jess struggled to manage for Doula.
At that moment, Rory was practicing braiding Doula's hair, her fingers fumbling slightly as she tried to mimic a tutorial she'd watched earlier. She'd realized recently how few hairstyles she actually knew, and with a daughter of her own on the way, she figured it was a skill she'd soon need on a daily basis. Sure, Doula was far from conventional, her upbringing all quirky and independent, but spending time with her gave Rory an intriguing glimpse into what her own future as a mother might look like.
It wasn't until later, after Doula had scattered off to her room to work on some crafts projects, that Jess joined Rory on the couch, a couple of pages in hand. Rory took a deep, tactical breath, bracing herself for whatever critique might come. While Jess usually offered plenty of praise, he'd learned that Rory responded better to constructive criticism. Compliments tended to make her squirm, so he didn't overwhelm her with them. Instead, he focused on what could be improved, knowing that for Rory, dissecting her work was as rewarding as perfecting it.
The chapters usually unfolded like a mosaic of Rory's memories—her college years at Yale, her struggles with imposter syndrome later on, feeling lost between two worlds, and the moments she'd had with the people in her life - most of all her mother, her friends, and also the men in her life. Time jumps were common. And even with some of the names changed, it was often still assumable for Jess who she was talking about.
"Okay, so… I find this bit interesting…," Jess pointed out, having circled a section on one of the pages, and continued to read out the excerpt:
"Whenever it all became too much—deadlines looming, expectations crushing me—I'd find myself whisked away. He had a way of making the world feel small and manageable, of turning even the worst day into an graspable adventure.
There was one particular night when the weight of it all came crashing down. I hadn't slept in two days, not to mention had a full meal and my desk was buried in crumpled notes. And then there he was, all the way from half across the world, leaning against the doorframe with that infuriatingly charming smirk.
'Pack a bag,' he'd texted me ten minutes earlier from the car. That was all the warning I'd gotten.
'I can't just leave,' I replied, arguing with him in person. Yet, I had, in fact, already by then, casually, packed my toothbrush and a change of clothes into my purse.
'Sure you can,' he said, assuringly, already grabbing my coat.
And just like that, we were gone — hours later standing under a canopy of stars in some tiny town I didn't even know existed. He'd brought me there to see a meteor shower, much like we had watched on a rooftop a long time ago. I hadn't even known it was happening - yet it was apparently one of these things that happened once in a decade. But he did. He always knew. He always remembered. Despite his own busy life, his family, his work… his fiance.
Sometimes I berated myself, thinking that letting him do those things to me made me seem flaky or easily swayed. But it was never about that. He never forced or manipulated me into anything. It was as if he instinctively understood what I needed — even when I didn't — and simply removed the option for me to deny myself. Just like he did during our final goodbye, our real goodbye, when he unknowingly left me with the most significant parting gift of all. A new purpose."
Rory swallowed hard. She'd fought with herself for hours, thinking whether to put that bit in there or not. It was a part she'd written earlier, back in fall, but only now decided to put into the chapter as it seemed to fit so perfectly for pacing purposes. Sometimes the heaviest parts were the hardest to place.
"So," Jess began, sitting at the edge of his chair as Rory settled onto the couch. "You've nailed the emotional weight of the moment—it feels raw, vulnerable, and deeply personal. But…" he paused, tapping the edge of the page thoughtfully, "I think you might be overexplaining in a couple of places. Like here," he pointed to 'thinking that letting him do those things to me made me seem flaky or easily swayed.' "It's honest, but it feels a little clunky, like you're circling the idea instead of just landing on it. You could simplify it—let the emotion carry the moment. Readers will get it without needing every detail spelled out."
Jess leaned back, his expression soft. "You've got a real knack for capturing the bittersweet—like that line about the parting gift. That one lands perfectly. It sticks with you. I know this might be a discussion for a later date - but you might want to consider leaving it as the very final paragraph of the whole book," Jess explained, trying his best to remain constructive in a way Rory expected him to be.
Rory sighed slightly, mostly from relief.
"I guess I could look it over," Rory exhaled. "Anything else?" she asked, bravely.
"Not right now…, but…" Jess stretched out, thinking.
"What?" Rory asked, just needing him to come out and say it.
"The guy in your book—the one who keeps whisking you away," Jess said, his eyes narrowing slightly. "It's that Yale guy, isn't it? The one who proposed to you?"
Rory froze, then shifted uncomfortably, avoiding his gaze. She'd never knowingly discussed the proposal with Jess, but he was family, so perhaps it was Luke or Liz that had mentioned something.
"Why does it matter?" she asked, feeling defensive.
Jess sighed, rubbing the back of his neck. "It doesn't. Not really. I just… Rory - is he the father?" he asked, hitting the nail on the head.
Rory's uncomfortable silence, along with her avoiding his gaze, was answered enough.
"I know it's not my business.. But a part of me believes... You wouldn't have included this in here if you didn't want me to know… or at least ask. You knew I might, right?" Jess added.
"That's why I didn't tell you," Rory said, her voice defensive but not unkind. "I knew how much you always disliked him. I didn't want that to color how you see me. Or how you see my daughter," Rory added.
"Sure, I'm no fan," Jess replied, snorting slightly, that being the understatement of the century. Jess wasn't going to point out how he'd also managed to google the guy and by now also knew how Logan was married and expecting a child very publicly, having briefly cast eyes on some red carpet photo of Logan and Odette.
"He was my escape for a long time," Rory admitted, her tone measured. "He made it easy to forget the things I resented or struggled with in my life. And it wasn't as bad as it sounds—he and his fiancée had an agreement. If anything, I was the one who wasn't handling my relationships well back then." She paused, hating how the explanation felt like another lecture on her mistakes, as if she were the villain in her own story. It wasn't untrue, of course—she had her share of blame. But it all sounded too much like she was making excuses for him, which wasn't her intention. It was about reckoning with her own reasons for choosing the easier path, for not saying 'no' to him when she should have.
Jess leaned forward, his expression softening. "Rory, I'm not judging you. I get it - things happen. But you deserve better than being someone's second priority," Jess spoke, softly.
Rory looked down, her hands resting on her belly. "I know. Believe me, I know. And I'm not expecting much from him. He's… trying, in his own way, but I'm not counting on him."
"Well, for what it's worth," Jess said, his voice steady, "you don't need him. If you ever need anything—anything at all—I'll be here. I'll be the best father supplement a friend can be."
"You're a lot more like Luke than you think, you know, right?" Rory replied, making this into a joke. It was too touching to take it seriously, she just couldn't let herself fall apart right now.
"Oh, yeah? What way?!" Jess teased back, lightly, having been caught by surprise himself how touching it had sounded, coming out of his mouth.
Pushing through the emotional moment with jokes, Rory stood to leave, the night getting late already. Her messenger bag slipped off the couch, landing on the floor with a soft thud. Rory bent down to grab it, but froze a second later, straightening slowly
"Oh no," Rory's voice stuttered.
Jess looked up, alarmed. "What? What's wrong?"
Rory's eyes widened as she stared at the growing damp spot on her shorts. "Either I just peed myself or my water just broke. I'm not sure which is worse…," her voice shook.