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As a kid, Rory Gilmore had always dreamed of traveling the world. She plastered her walls with posters of far-off lands, pored over outdated guidebooks in the library, and dreamed of museums and castles and cliffs over the ocean.
Of course, reality has a way of twisting those childhood dreams. Sure, she travels for work, but it’s to places like Dallas or Portland or (oh god, never again) Boise. She’s gone to London a few times, hopped over the Channel to see Paris again, but that’s about the extent of her travels.
Luckily, she gets sent to New York a lot. She loves the city, even though every time she passes the Times office, she feels a little bit sick.
She has the same basic routine for her trips there: hit the bagel place on the Bowery, wander through the New York Public Library, cut through Central Park to get to the diner with incredible burgers that’s right next to the Museum of Natural History (a childhood favorite), and then a quick subway ride to Washington Square Park.
It’s a tradition with her: every solo trip to the city leads her to the park, from the very first terrifying journey in an unfamiliar city to now, when she walks the streets like a native, even though any real New Yorker would know she wasn’t.
She came after her interview at the Times , the one for the fellowship that she pinned every hope and dream on. The interview had gone well, but she was still nervous and she hated the way everyone in her life was so sure she’d get it. Her mom wouldn’t hear any of Rory’s worries, her grandparents were already checking real estate listings in Midtown, and Logan…..once she finally got ahold of him on the phone, she knew he would just grin and say “You knocked ‘em dead, Ace. They’re probably gonna skip the fellowship and just offer you a full-time position.”
And yeah, it’s nice to hear that people have faith in you, but sometimes you need the truth. You need reality. You need someone to look at the situation from the outside and give you an honest evaluation. For Rory, that meant Jess. It always had, even though it wasn’t like she could call him up to chat, not after the way they’d left things in Philadelphia.
She had left the Times office and, without really realizing it, her feet led her through the streets, down the subway stairs to catch a train, and then she was there. Washington Square Park. It took her a little while, but when she finally found the bench, his bench, she was almost surprised to see that there was no one there. He wasn’t there.
And why would he be? It was ridiculous, but a small part of Rory’s brain had frozen this place in time and for her, there would always be a dark, tousle-haired boy sitting on this bench, eagerly devouring The Electric Kool-Aid Acid Test .
Even though Jess wasn’t there, and probably hadn’t been for years, Rory still sat down. Her feet hurt; the interview shoes she picked for today are not walking shoes, not even a little bit. She sits and she thinks.
Yes, the interview went well, but she’s not delusional. She knows that getting this gig is the longest of long shots, and that’s okay. Sometimes you need to take the long shot. But she’s worried about what her mom and her grandparents and Logan will think and then suddenly a voice in her head says, “ Who cares? They love you and, geez, you tried, it’s not like you didn’t try. If you don’t make the cut, I’m sure everyone will find a way to go on, including you .”
It’s exactly what she needed to hear and exactly what Jess would say if he was there, so maybe that’s why she keeps going back.
Every trip to the city means another hour or so on the bench, reading and listening for that little voice in her head to help her untangle the perpetual knots in her stomach.
When she starts missing Logan and wonders if maybe she should’ve married him after all: “Aw, come on, Gilmore, are you insane? Have you lost the last of your marbles? Married? At, what, 23? That’s too boring for a Christiane-Amanpour-in-the-making .”
When she gets a job offer at a small paper in Santa Fe: “ You’d never make it through a southwest summer .”
When she worries that journalism might not have been her calling after all: “ As soon as you stop loving something, it’s time to quit, but you totally still love being a journalist, so don’t hang it all up yet. ”
It’s funny because she knows that if she really needed his advice, she could get it. She’d be well within her rights to shoot him an email and reestablish a proper, grown-up friendship with him, but she’s scared. Sure, they’re both adults now (even though she feels awfully young for 26), but with all the drama that transpires between them every time they meet, it’s just easier to keep things imaginary.
She’s in New York today for a meeting with The Observer tomorrow morning. She thought she’d get there a day early, think things over on her bench, and then wander through the Met for a few hours.
She’s feeling a little unsure about her next move and wants to see if that little inner voice has any advice. It’s a good plan, a plan that she’s carried out a dozen times before, and she doesn’t anticipate anything unexpected.
So when she arrives at the park entrance closest to her bench and sees someone sitting on her bench, the back of their head somehow looking smug, she marches over, ready to fork over twenty bucks for a little peace of mind.
“Excuse me,” she begins, but as the head starts to turn, she recognizes the messy hair and the scar on the back of his hand and oh God, he’s reading Out of Africa .
He doesn’t look surprised to see her. Just like the first time she found him here, he smiles up at her and closes his book.
“Well, of all the gin joints,” he drawls and Rory feels like she’s on the verge of hysterical laughter because he’s here, he’s here, oh my God, he’s actually here .
“This feels familiar,” she finally chokes out and Jess’ smile widens just a little bit more.
“It certainly does. Shouldn’t you be in a plaid skirt and saddle shoes?”
“It’s not a school day,” she says primly, taking a seat next to him.
“Ah, of course. For us high school dropouts, there’s no such thing as a school day, so you understand my confusion.”
“What are you doing here?” She blurts out, bringing the banter to a crashing halt.
“I live here,” he raises an eyebrow. “Luke didn’t tell you?”
“He probably didn’t think it was important,” Rory bites her lip. “I’m not in the city that much, so….”
“No need to warn you about the big bad wolf?”
“Jess,” she sighs and it feels so familiar, that tone of exasperated fondness, that it scares her.
“Luke still thinks you’re an innocent little girl and, even though I’m respectable now, he still thinks I’ll hurt you somehow.” Jess is smiling as he says all this and it surprises her because the old Jess would be so incredibly frustrated that no one seems to trust him.
“Are you still with Truncheon?” She wants to gloss over any mention of the past, worried it will only end in more heartache for the two of them.
“Yeah, but we’re thinking about opening a New York office. I was chosen to come up early and scope the place out, find us an office and everything.”
“And have you?”
“We’re about to start paying a king’s ransom for a brownstone in Brooklyn.” He rolls his eyes. “I’m gonna have to write another book just so we can break even this year.”
“I’ll make sure to buy a copy. Can’t have you out on the mean streets of Brooklyn with all those hipsters and vegetarians.”
“Ugh, don’t remind me,” he groans, shaking his head sorrowfully. “Take my mind off of it. Tell me what you’re doing here.”
“Job interview.”
“Where?”
“ The Observer ,” she blushes a little. “It’s not exactly hard-hitting journalism, but-”
“But it’s something,” Jess finishes. “And if it’s something you love doing, then who cares about the rest of it?”
And there it is. That little voice inside her head, except this time it’s coming right out of Jess’ mouth. Rory just barely stops her own from dropping open.
“Um, yeah,” she smiles quickly, tucking her hair behind her ears. “Yeah, you’re right.”
“Don’t sound so shocked.”
“I’m not!” She laughs, leaning forward slightly. “You’re just weirdly good at the whole advice thing.”
“I’ve made a lot of mistakes,” he shrugs. “Seems like someone should learn from them.”
“But not anymore,” she says quietly. “At least, not really.”
“Rory,” he’s laughing and it makes her feel like a kid again. “Just because I’m not stealing garden gnomes and getting in fistfights behind the bleachers anymore doesn’t mean I don’t still make mistakes. ‘To err is human’ and all that.”
“‘To forgive, divine,’” Rory finishes the quote. “Alexander Pope. One of my grandfather’s favorites.”
“Eh, a little dry for me, but I guess I can see the attraction.”
“Well, they can’t all be Ginsberg and Thompson.”
“More of a Lester Bangs man, myself.”
“God, again with Almost Famous !”
They both laugh because it’s a conversation they’ve had a million times before but it seems almost silly to be doing it as adults in New York City. It’s nice, though. Rory missed this, missed him. She thinks he might have missed her, too.
“You got any free time in that schedule of yours?” he says suddenly and it makes Rory’s mouth stretch into a blinding smile.
“I think I can carve out an hour or two between the Guggenheim and the Frick.”
“The Frick?” Jess makes fake puking sounds. “The guards in there always yelled at me when I was a kid and the art is just so-so.”
“I take it you’re a MOMA fan,” Rory rolls her eyes as they both get up and start meandering towards the street.
“Nah, I’m all about the Met,” he shoves his hands in his pockets. “The American wing with that huge glass room, you know, with the front of the house in it? Great place to hang out and read.”
They keep talking about everything and nothing as Jess leads them down the street and Rory doesn’t even think about where they’re headed until they come to a stop in front of-
“The Strand!”
“Don’t tell me you’ve never been here before,” Jess groans as he notes the unusually strong tone of excitement in her voice.
She punches him lightly on the shoulder. “Yes, I’ve been here before, Mr. True Blue New Yorker.”
“Good,” he grins. “Now come on.”
They wander through the stacks, upstairs and down, and by the time they decide to call it quits, they both have an armful of books.
“Here,” Rory holds out Inherit The Wind and The House of the Spirits . He accepts them as he hands her The World According to Garp and The Bonfire of the Vanities . It was always their regular book shopping routine and Rory likes that they both fell back into it so easily.
From there, they take a train that spits them out at 72nd Street and Jess lets Rory drag him into a Thai place for lunch.
It’s here that Rory hears about the second book that was published last year (the one he sent her in the mail with no return address or name at all, but she knew it was him) and how it’s gaining some traction, which is why Matt, Chris, and their accountant are urging him to start a third.
It’s here that Rory tells Jess about Logan proposing to her right before graduation and, to his credit, he only snickers a little bit.
“Married? At, what, 23?” he snorts. “Imagine how bored you would have been.”
It’s here that Jess casually mentions that he’s been dating people, but no one’s stuck yet. Rory, a blush rising in her cheeks, says, “Me, too.”
“Huh,” Jess grins, leaning back in his chair. “Well, aren’t we quite the pair.”
After a few solid minutes of haggling, they end up splitting the check (Rory wore him down) and heading off again.
“The Met?” Rory guesses as the palatial building comes into view. “God, you’re predictable.”
“You were totally planning on coming here, even before we ran into each other.”
“Maybe.”
“You’re more and more like Lorelai every day.”
“You sound like my grandmother.”
“Hey, take that back!”
They join the stream of tourists jostling their way through the doors and quickly make their way to the Charles Engelhard Court (Jess tells her only tourists and docents refer to it like that, but Rory likes the regal sound of it). Rory hadn’t told Jess, but this is her favorite part of the Met, too. They wander among the sculptures, both stopping in front of a bronze statue of a woman pointing a bow and arrow off into the distance.
“Diana,” Jess points to the plaque in front of them.
“Yeah, the bow and arrow sort of tipped me off.”
They stand in silence for a beat longer before Jess speaks again.
“Rory?”
“Yeah?”
“Why were you in Washington Square Park this morning?”
She turns to face him slowly, unsure of how to put it all into words. His gaze is strong and steady, which reassures her somewhat.
“Because….” she presses her lips together in a nervous smile. “Because I always go there when I’m in town.”
“To the park, or to that bench?” There’s a light in his eyes that Rory thinks might be hope. That, or suppressed mirth at the inanity of her actions.
“The bench,” she shrugs and then the dam inside her breaks and the words start flying out. “I started going after I had this interview at the New York Times , back when I was still at Yale, I mean. I was worried about how it had gone and I wasn’t sure I would get the job, but I couldn’t talk about it with anyone because they were all so sure I was in, and it was sort of driving me crazy, and before I knew it, I was in the park and sitting on the bench and then I heard this voice!”
“Don’t tell me,” Jess looks close to laughing, but Rory can tell he’s fighting the urge, for her sake. “You finally find God, Rory?”
“No, you don’t need to send me to the funny farm quite yet,” she nervously tucked her hair behind her ears. “It was….it was you. Kind of.”
“Me?” The smile on Jess’ face isn’t as wide and he looks confused.
“I was worried about what my mom and my grandparents and Logan and everyone would think when I didn’t get the job and suddenly I hear this voice in my head that sounds an awful lot like you telling me I tried and that’s what matters and they love me and they’ll get over it.”
“Well, I was right, wasn’t I?” He snorts, and Rory can tell he’s still trying to understand all this. Hell, so is she.
“So whenever I’m in town and something’s really bothering me, I go sit there and read and wait for that little Jess voice in my head to help me figure things out.”
She’s finally done rambling and she looks at Jess, waiting for him to say something.
“You know, I have this thing called a telephone,” he smirks. “I’m pretty sure you do, too. If you really needed my advice-”
“Shut up,” Rory groans. “It’s different.”
“No, no, I get it,” Jess chuckles. “I’m the voice of your conscience. Like Jiminy Cricket, but with a little more cynicism.”
“A little?”
“Okay, a lot.”
“God, I sound like a total psycho, don’t I?” Rory buries her face in her hands. “I should have never told you.”
She feels his hands on her own, tugging them away from her face. They are still as warm and rough as she remembered.
“You’re not psycho,” he says, his dark brown eyes so close to her face she feels like she’s drowning in them. He’s still holding her hands. She tries not to notice. “You think I never heard your voice in my head? Telling me to write? To take out the chapter with the weird dream about Gore Vidal in it? To call Luke every couple weeks?”
“So,” she says slowly. “I’m your Jiminy Cricket?”
“Sure,” he snorts. He lets go of one of her hands, but keeps holding on to the other, his grip loose but reassuring. “Now come on, I know you’re dying to do the When Harry Met Sally scene at the Temple of Dendur.”
“It worries me that you know what it’s called.”
“I told you, I came here a lot as a kid!”
“Nerd.”
“Hello, pot? This is kettle. You’re black.”
They spend another two hours in the museum and Jess doesn’t let go of her hand once and Rory would wonder if this was a dream, except for the fact that she’s never dreamed anything like this before because she always thought she had opened and shut that door for the last time in Philadelphia. She had thought there was no future for the two of them, beyond being sort-of cousins and making polite small talk at holiday gatherings.
But it turns out there is a future and this future is bookstores and Thai food and the Met and ice cream from a cart in Central Park and when Jess jokingly says “In cones ,” Rory thinks her heart skips a beat.
She kisses him on Bow Bridge and, even as her lips are pressed against his, she thinks, oh my God, what a cliche but he doesn't seem to mind because he wraps his arms around her waist and pulls her closer and Rory stops thinking about anything but the feel of his hands on her skin.
When they finally pull apart to catch their breath, Jess smiles, the same smile he used to give her when he thought no one was looking.
“Careful, Gilmore,” his eyes crinkle up at the corners. “You’re gonna have the tourists thinking romcom junk like this happens every day here in the Big Apple.”
“Only tourists call it the Big Apple,” Rory grinned back. “God, you’re embarrassing, Jess-”
And then he’s kissing her and Rory is falling headfirst towards something that isn’t quite love, not yet, but give it a day or two, and she’ll be head-over-heels.
They pull apart again and continue walking, both with dopey smiles on their faces. They don’t talk about the kissing because, really, what needs to be said? This moment, this sunny spring day in New York, is as close to perfect as either one can imagine, so who needs to discuss the details?
“Hey, Jess?”
“Yeah?”
“What were you doing in Washington Square Park this morning?”
“Would it be cheesy to say I was waiting for you to come find me again?”
“Unbelievably so.”
“I was reading Out of Africa .”
She takes the job with The Observer and this time, she doesn’t need to make the pilgrimage to Washington Square Park to hear Jess’ voice say, “ You’re gonna love it here, Gilmore ,” but she does anyway because it’s tradition.
This time, she walks into the park with his hand clasped in her own and when he says she’s gonna love living in New York, she just smiles and says, “I know.”
For the first time in a long time, Rory is sure of what she’s doing.
It feels good.