Not Unlike Ross and Rachel
Rory and Nate. Nate and Rory. It's a mess. Obviously.
Note: Spot the Political Animals nod!
"Most surreal New York moment?" said Nate. "The earthquake."
"Or Paz de la Huerta," suggested Serena.
He posed the question, "How about our illustrious Gilmore girl?" with a large grin spreading across his face.
Nate got up and shook hands with his newest employee. Serena squinted as she sharpened her vision. His arms twitched in a way that suggested he was going to hug her but thought better of it.
"Rory, hey, how was your flight?" asked Nate.
Rory let a dramatic exhale escape her and flipped her hair. "You mean the helicopter flight after the first-class plane trip after the town car ride from my hotel room in Washington to New York –"
"But …"
"– all of which you paid for?"
"Well …"
"With the company budget?"
"I …"
"That's some irresponsible spending, boss, if I must say so myself."
"Boss?" Serena, amused, raised her eyebrows. "We're co-workers?"
"As of approximately two minutes ago." Rory succinctly nodded. "I just handed in my first story to Tina."
"She works fast," said an impressed Serena.
"It's the coffee," Nate and Rory said in unison.
Rory Gilmore slowly raised her head, sore and exhausted, despite the painkillers. She groggily watched Nate Archibald from the sweaty, rumpled hospital bed as he held their newborn daughter. He gently cradled the pink bundle of baby to his chest in his smock-like hospital gown, and she had never seen him so happy. He was grinning as if the wriggling thing in his arms was the solution to all the world's problems. And maybe she was. She was a Lorelai Gilmore, after all.
On her birth certificate, it read: Lorelai Amelia Gilmore Archibald. No hyphen. Very Hillary, if Rory said so herself. She and Nate had agreed to call her Isla. She suggested the name Ivy – as in IV, as in the fourth Lorelai – somewhere around her second trimester, impressed with her wit, but he had shot that idea down instantly, and then she remembered Ivy Dickens, the lying blonde rat that somehow managed to survive the sinking of its self-made ship. So a big fat NO to Ivy. No Lola, because they already knew one of those as well – nice girl, though. And then there were vetos against Lori, Laura, Laurel, Ella, Elle, Ellie, Riley … The No List was long.
There were a lot of no's until Serena said, "Hey, how about Isla?" at brunch one Sunday morning in Chuck and Blair's beautiful new townhouse. Rory liked it. Nate liked it. And, most importantly, High Priestess of the Upper East Side, Blair Waldorf-Bass liked it, and her word was law. It was impossible for Rory to have known her grandmother back when she was Emily Laurent, young and terrifying tyrant at Nightingale, but since meeting Blair, Rory felt like she had.
Blair and Serena, and Blair's husband Chuck, and Serena's boyfriend Dan were sitting in the maternity ward waiting room, a family Rory wouldn't have chosen for herself – and she wasn't entirely sure Nate had either – but a family, nonetheless, cultivated out of necessity, habit and (at times, reluctant) unconditional love over a quarter of a lifetime and counting. They were insane and dysfunctional and almost literally incestuous.
Serena van der Woodsen and Dan Humphrey shared a half-brother, and were step-siblings for a time. Rory's addition to the group had been interesting when Blair grilled her over lunch, imperiously stating that it was "for Nathaniel's own good, given his past paramours." She and Blair eventually realised they themselves were distantly related by marriage through Emily Gilmore and Blair's mother, Eleanor Rose, formerly Waldorf, née Laurent. They weren't close enough relatives to even really call themselves cousins with a second or a third and a few tacked on however-many-removed's, but the coincidental link was there.
Then there was the fact that most of these people had slept with each other. Nate had dated Blair for almost half his life, when they were kids, and lost his virginity to Serena when they were teenagers. Blair also had a relationship with Dan, though it was obvious to blind, deaf and dumb aliens that she and Chuck were fated by the cosmos.
Rory was stunned to discover that her college boyfriend, Logan Huntzberger – who she had absolutely no contact with, should anyone ask – had slept with Serena on a number of occasions, and that Stephanie and Tripp Van der Bilt were Nate's cousins. Her history with Tripp was … well, it was embarrassing. She had still attended his wedding to Maureen, and was surprised that she hadn't met this obscene gang of overprivileged children playing adults sooner.
These people were unwholesome in a way Rory hadn't been prepared for – which included her experiences with Yale's outrageous super not-so-secret society, the Life and Death Brigade – but it was fine because they were uncompromisingly protective of their own, which now included Isla.
Rory observed Nate's deep blue eyes, obscured by that fetching thousand-yard stare of his, him almost squinting from smiling so widely in his apparent happiness that it had to hurt at least a little. He was so happy, and she felt …
Rory didn't really know what she was feeling, to be honest. She had kept the baby, so that was something. She couldn't have been raised by Lorelai Gilmore and taken the other option. Though if she hadn't been, Rory was fairly certain that she would have booked an appointment at Planned Parenthood. She had never been comfortable with the idea of pregnancy, or pregnant people, or the tiny humans that resulted from impregnation.
Rory had wanted a c-section, to be unconscious during the disgusting ordeal, but her mom had insisted that the miracle of life was something she needed to experience. She regretted her decision to do it the old-fashioned way, except for the drugs – thank medicine, for the drugs. Although, she had liked that she got to feel the joints click and the small bones strain in Nate's hand as she squeezed the hell out of it. There was definitely a welcome catharsis in that. This was his fault, too.
They weren't married. They weren't even really together. Never really had been.
Rory used to work at The New York Spectator, and Nate was her boss when they started not-quite-dating. He had just gotten out of a relationship with a teenager – a teenager in high school! – and she hadn't had dared much of a dip in the dating pool since the mess with Tripp – before he went to prison, for the sake of specificity.
There was a glimmer in Nate's hand, and Chuck cocked his head. "What is that?"
"Huh?"
"In your hand. What is it?"
"Oh … I guess it's nothing, really."
"Come on, Nathaniel," said Chuck, his patience beginning to wear thin. "Tell Chuck what's going on. Is that what it looks like?"
"Sure."
Chuck arched an eyebrow the instant he recognised the item that he had been handed. "Why do you have your mom's ring?" It was a question to which he already knew the answer – the eventual marriage of Nate Archibald and Rory Gilmore was expected by practically everyone who knew them – and of them – after all. But it didn't make sense in the context of Nate's obvious depression.
"I still have it because … because she said no."
"Hey!"
Lorelai gasped as her daughter lightly plopped down on the gazebo stairs next to her. "Just land in Teterboro?"
"That's how you say hello?" said Rory, unable to keep the grin off her face. It had been an unbearably long time since they'd seen each other.
"You're still using one of the corporate jets, aren't you?"
"No."
"Yes, you are!" accused Lorelai. "You're still using one of the corporate jets!"
"The corporate jet, as in there's just the one," objected Rory. "And no, I'm not."
"No you're not still using 'the' corporate jet?" she rebutted with emphasis.
"No, I'm not using any jets of the corporate variety. We're the Spectator, not the Times."
Lorelai frowned in disbelief. "So that's how you look when you get off a commercial plane?"
"You're very obsessed with how I got here today." Rory was smiling at her, amused. "I'll have you know I drove myself in my own car from Tweed-New Haven."
"Not JFK or LaGuardia?" Lorelai put on a frown, which Rory quickly matched, so she quickly moved on in her usual manner. They weren't as close as they used to be, which was a shame, and there were certain subjects they couldn't touch without it getting sticky, which was a disappointment Lorelai tried to keep down for fear that her daughter might stop speaking to her again.
"No more chauffeurs and town cars?" continued Lorelai lightly. "That's one heck of a hard knock life you live there, Annie. I'd say something to van der Granddaddy Warbucks before your fancy Upper East Side penthouse gets downgraded from a triplex to duplex."
"My actual life in New York and the life you envision me living in New York do not belong in the same reality."
"Did I imagine the black cars and big penthouse?" Lorelai lifted a mildly judgemental eyebrow – mild.
"… No," Rory said after a palpable pause.
Lorelai made a triumphant "Hah!"
"You really need to stop calling Nate's grandfather that," backtracked Rory, picking up the Annie reference.
"William doesn't mind," said Lorelai, shrugging.
"Nate does."
"So, the husband, how is he?"
"You've gotta stop calling him that."
"Well, he is one." Lorelai looked at Rory pointedly. "Yours."
"Not for long."
"So you're actually going to go through with it?"
"Um, yeah," said Rory, no-nonsense.
"Sometime this century?" needled Lorelai.
"We have the lawyers and the paperwork."
"You've also been sitting on your asses and twiddling your thumbs."
"It's not that bad."
"Kid, I think there's a reason why you still haven't gone through with it."
"We are getting an annulment – well, divorce. Apparently we're too Ross and Rachel, all tangled up in each other's business –"
Lorelai interrupted, "You mean with a child –"
"– and can't just get an annulment," continued Rory.
"– and a house?" finished Lorelai.
"Which is why this is taking so long," said Rory.
"Uh-huh."
"Nobody's twiddling any thumbs!"
"Sure."
"And it's a condo, not a house," Rory corrected.
"Ah, yes," said Lorelai, poorly feigning sage wisdom. "And that makes it a little less complicated.
Sunlight had started spilling through the thicket of high-rises and black cherry trees, but the early morning air still stung their nostrils as they heavily breathed through them. Father and daughter had wound down from their heated sprint through a clear stretch of Central Park, slowing to a relaxed stroll, amiably shoulder-to-shoulder.
"Nice try, old man!" chuckled Isla, victoriously tossing her wavy brown ponytail. Streaked with gold, it perfectly matched the sweaty, wind-swept hedge atop her dad's head, save for the distinguished streak of grey in his hair.
They had spent July building a sailboat with her grandfather up in Maine, until Governor Archibald had to return to New York, being a grown-up with a grown-up job with grown-up responsibilities. Isla came home a little tanner, frecklier and blonder than her dad when he did, spending the rest of her summer out on the ocean.
Nate laughed heartily. "Maybe next time."
Isla peered at her dad, her large, vividly blue eyes alight with curiosity. "The endorphins?"
"Hm?"
"You don't look like you wanna tear your hair out," she said simply, and then made of show of yanking her long ponytail.
Nate appeared amused, mostly, though a definite smattering of bemusement had swept over his apparent amusement. "You think I usually look like I want to tear my hair out?"
"I would say 'only when you're up for re-election' –"
"Which I am," he said, frowning slightly. Isla knew that was his least favourite aspect of public service. Kissing hands. Shaking babies. Putting on a show. Personally, she didn't mind it. She had always loved the circus.
"– or 'when Ms Shafai-Koç-Cashman is in between husbands' …" Isla unsubtly trailed off, a cheeky grin tugging at the corners of her mouth.
Nate sighed, this time the heavy gush of air had been expelled from his long-suffering.
"But I think you've looked like you want to tear your hair out since I discovered boys."
He turned his expression of suffering on her, and Isla grinned. She wasn't wrong.
She then added, "Who weren't practically my brothers," thinking of Tim and Henry and Milo. Because, gross.
Isla slung a careless but no less affectionate arm around her dad's shoulders – something she had proudly been able to do since she'd shot up to a skyscraping six foot at the age of fifteen. "So … why the happy?" she pressed.
Nate sighed again, somehow deeper, and she suspected for entirely different reasons. "Your mom –"
Isla's expression flashed through incredulity to anger to resignation in rapid succession, like a malfunctioning traffic light. "She's back." She nodded harshly, her annoyance obvious. "I'm not even gonna bother asking 'for good this time?' I feel like I'm five again – no, wait, I feel like a street urchin asking for 'more' every time I do. How long's she gonna be here for?"
"Dunno," said Nate, his eyes fixed on some undeterminable point ahead of them. "She's in the city. She's not alone. They're going to be at brunch."
"There's a 'they're'? Who's the they?"
"Just her and Emma."
She began chuckling hollowly. "So she's started dragging Emma into her messes. Great."
"Isla …"
"Great parenting. Really," she thickly laid on the sarcasm. "I don't know how you raised me without her."
"Hey, you know it wasn't like that," Nate defended her mother.
"I'm not trying to make this about me, but – I just – I feel bad for Emma, you know?"
Emma was supposed to have the proper two-parent thing Isla didn't.
"And you," said Isla quietly.
Nate's eyebrows skyrocketed. "Me?"
"Just …" Isla chewed on her bottom lip. "Just don't let her hurt you again, OK?"
Sweatshirt hood up and head bowed, Emma was intently doodling on her forearm with a black pen and ignoring a room full of people she didn't know enough to dislike but knew if she did, she probably would.
The room immediately grew louder with sudden appearance of the smiling, ten-foot swimsuit model who could only be Emma's older, better, brighter half-sister. No, that wasn't bitterness. Isla had entered the room in an angelic ring of light, radiating real smiles and kind words and oodles of that damn Archibald charm.
Gabriela Geller-McMaster sighed. "We leave you alone for a minute –"
"One minute –" reiterated Henry Waldorf-Bass.
"I can't believe we got arrested," grumpily interrupted Gabriela's brother, Tim.
"I can't believe I couldn't talk us out of getting arrested," Isla Archibald said incredulously.
"I can't believe your rack didn't get us out of getting arrested," stated Milo Sparks, puzzled.
"What?" Henry asked sharply.
"She flashed the cops who handcuffed us."
"WHAT?"
"I smiled at them, too, if that makes you feel any better."
It was Thanksgiving in the year 2029, and things were remarkably the same, for all that they had changed. Chuck was CEO of Bass Industries, whereas Blair had stepped back from the design aspect of Eleanor Waldorf Designs, focusing solely on the business side of her company while also launching her own fashion magazine, The Waldorf-Bass Book, under the publishing umbrella of Spec. Inc.
Spec. Inc. AKA Spectator Incorporated AKA The Humphreys' Time-Shared Multimedia Empire. Dan had taken over the news outlets and Serena all things infotainment. Nate still owned the company, but he hadn't had the time to run it years, nor had he been allowed to have any kind of hand in private interests since January.
Chuck's lips curled into an open smile as he re-entered the dining room. "I found something of ours at the front door."
Two tall figures languidly loped in behind him.
"Isla!" exclaimed Serena, joyously clapping her hands together. "Nate!" She got up to hug them both, and then warmly ushered them to their usual seats across from her and Dan, with Henry to Isla's left and Jenny to Nate's right.
"We were starting to worry you wouldn't be able to make it," said Dan.
"You can thank Elaine for winning the nomination," said Isla cheekily, earning an uncalled-for hair-ruffle from her dad.
Nate shared a self-depreciating smile with everyone as he sat down. "I'm just our humble VP and thankfully don't shut down the entire city every time I visit."
"Here, here!" said Eric, raising a glass.
"Here," said Blair, primly pointing to specific spots on the table, "and here." As had become Waldorf tradition, she relegated Dan to the waitstaff despite hiring professional servers, happy to boss him around more than usual.
Dan laid the dishes down exactly where Blair had specified and sat down next to Serena before she got the chance to add yet another task to his pretend job for the day.
"It's so nice to be needed," said Dan flatly.
Serena shot Blair a joking glare. "And thanked for it."
"I don't know what you're talking about, Humphreys," addressed Blair lightly as she daintily sat at her head of the table.
Henry sensed six feet of sugarplum-scented sunshine filling the empty seat next to him.
"H!"
He hadn't been in the mood for sun lately.
"Henry!"
He pursed his lips and resolutely kept his gaze fixed on his empty plate.
"C'mon, H," hissed Isla Gilmore Archibald exasperatedly, "you're gonna have to talk to me eventually."
Henry Waldorf-Bass was seventeen years old and – justifiably! – angry at the world. Or maybe just at his best friend, who had moved away in the middle of the school year because her dad got some dumb new job.
Inconsiderate and totally unacceptable, the pair of them.
Isla would be turning seventeen soon herself, and was determined to have Henry's forgiveness before she celebrated another year. It wasn't the best situation, but she was glad to have something to do.
A goal. A distraction.
Because she was currently in the sticky predicament of being in love with her dad's boss's incredibly beautiful but very gay son.
TJ Hammond had asked to sleep with Isla because he wanted to "make sure" and Isla, the love-struck idiot that she was, told him it was "OK." Afterwards, he said he liked her boobs but was "definitely gay." She kept to herself that she was definitely in love with him.
Isla had no idea what she was doing or what she should do.
"You may as well give up, Archibald." Holiday rolled her eyes. "He's been sulky all year – I think he's stuck this way now."
Holiday Waldorf-Bass was ten years younger than her elder brother, infinitely smarter than him – should anyone ask her – and an absolute terror to everyone except Delilah Humphrey and, occasionally, Isla.
Isla was the undisputed favourite child of the Archibald van der Humphrey Waldorf-Bass clan. Everyone liked Isla.
Except apparently Henry right now and TJ Hammond in the only way that mattered.
Almost everyone liked Isla, but Isla didn't like everyone.
Notably absent was Rory Gilmore, estranged mother to Isla and separated wife of Nate. She and Nate had eloped on Chuck's yacht a few years after Isla was born and immediately regretted it. They had only been dating a few months when the "happy accident" they named Lorelai Amelia Gilmore Archibald happened, and despite the necessary friendship they needed to cultivate as co-parents, they never put any further work into their relationship and had divorce papers drawn up within days of exchanging vows.
The papers, all unsigned, remained in the bottom drawers of their respective home offices.
Nate placed a fresh, steaming cup of coffee in front of Rory.
"Wh― Oh, hi, Nate. Thank you. You didn't have to do that."
Nate left, only to quickly return and place a stack of legal pads in front of Rory.
"Um … thanks for these too, I guess. A writer can never have too many legal pads at their disposal."
Nate left again, came back again, and placed a handful of different coloured pens on top of the legal pads.
"Uh, Nate, not that I don't appreciate all this, but why?"
Nate didn't leave this time, just reached into his jacket pocket and recovered a small velvet box – the kind of velvet box that Rory had been all too familiar with before.
"Nate … what's going on?"
Nate looked serious.
"A proposal."
"What kind of proposal?"
"I think you know what kind of proposal this proposal is."
"OK."
"A real one this time."
"Well."
"A real proposal for a real wedding and, hopefully," he said earnestly, "a real marriage."
"Um, the coffee? OK. The coffee, I get. Great incentive. Good job, there." Rory shook her head, baffled. "But the legal pads?"
"I know you, Rory."
"OK …"
"I know you'll probably want to make several pro-con lists before giving me an answer," he smiled warmly. "To my proposal." He nodded gently at her. "So, I'll just leave you to it, and …"
Rory exhaled deeply and crossed her arms. "You do know me," she harumphed good-naturedly.