AN: So this is the Christmas story I mentioned in my Amelia Lane and Later updates. It is not meant to be a long story, the chapters will be shortish, probably 2000-300 words, and it will be maximum 10 parts, maybe less. It is just meant to be fun. I was inspired by the Netflix film Holidate and I will take some cues from that, but the content will be original. In this story, Lorelai and Christopher married and stayed married, they had no other children. Rory went to Harvard, Logan to Yale. And we are going to pretend that they are 30 and 32 years old respectively in present day. There might be some mild M moments, but I will add that to the A/N or disclaimers in those chapters. Enjoy
Disclaimer: I do not own Gilmore Girls or the characters, or Holidate.
Part One - Thanksgiving
"You've got to be kidding me, baby brother," Honor Huntzberger-Montgomery glared at her brother who was eyeing his date from across the room, "does she charge by the trick or by the hour? Or did you get her for the entire night?"
"Relax Honor," Logan rolled his eyes, "I met her on the weekend with the guys, she's fine."
"Yes, I'm sure she is fine when you are out with the guys, but my children are here. This is a family event."
"Family, plus…what, seventy or so random people Mom and Dad felt the need to give thanks with? There is a coat check, and a valet Honor. This isn't a family event."
"You work with these men, Logan…do not do this at Christmas. Christmas is a sacred time, and I do not want to question if the woman my children are talking to with Uncle Logan is actually a hooker."
"I've never paid for sex, Honor. Thank you for your concern. I'm going to go check on Tiffany," Logan pushed himself away from the bar and walked across the expansive formal room at his parents Hartford estate. He was thirty two years old and single, being groomed to take over the family business at a pace that felt much too slow for his liking, but he was sure his father would kick the bucket eventually. In the meantime, every single time he went to a family event, a company party or a holiday, he was hounded with questions about who he was dating, when he would settle down. More often than not, his mother would hound him in the weeks prior with text messages about the daughter of a friend who was recently single and would love to meet him. Of course they would love to meet them. He was young, wealthy, worked out six days a week, was in great shape, more than easy on the eyes and he could carry on intelligent conversation. What he didn't need was a woman who had a stamp of approval from his mother or her society friends trying to hook up with him to advance her own status. He had only brought a date in an attempt to keep people at bay for the evening, but he saw Honor's point, this probably wasn't the right girl to achieve that goal.
"Tiffany, of course," his sister rolled her eyes as she watched him saunter across the room to the woman in a dress that barely covered her ass or her boobs.
"Hey there," Logan smiled as he stepped beside his date for the evening, "enjoying yourself?"
"Logan there are like…so many old people here."
"Why don't we grab a drink?"
"Your drink is full," she commented.
"I can get you a drink," he suggested, hating that this woman was almost immediately proving Honor's point, there was no reason he had brought her other than to piss off his parents.
"I'm bored."
"Tiff, you said you wanted to come to this, remember."
"I know, I just…I thought it would be more…fun."
"What can I do to make you think this is more fun?" Logan smiled at her, his intentions clear.
"I think I'm gonna go. Walk me out? If I leave now, I can probably make it back to Manhattan to meet up with some friends. Care to join?"
"Tiffany this is my family Thanksgiving," Logan followed her as she began walking towards front of the house, he certainly wasn't going to beg her to stay, but he also wasn't about to be embarrassed like this.
"Really, it's been fun," Tiffany was on her phone now, he assumed she was requesting an Uber and he stood with her awkwardly while she sent a few messages before loudly sighing, "time to go, call me if you want to get together back in the city?"
Logan watched as she walked away, he waited for a moment before stepping out onto the front porch and leaning back against the brick walls, "fucking bullshit," Logan muttered to himself.
"Logan?" the voice of an older woman brought him out of his own thoughts, "Logan is that you?" she was looking at him now as she walked up the driveway, "Richard, is that Logan?"
"Emily Gilmore," Logan pushed himself against the wall and walked towards the couple, a few steps behind them was a woman he assumed was related to them, she looked to be about his age, brown hair, blue eyes, she looked completely appropriate for this kind of a party, "sorry, I was just…getting some air for a moment."
"That is nonsense, come inside Logan," Richard Gilmore looked at the boy he had known since he was a child, "it can't be that bad."
"You have no idea," Logan shook his hand before turning to the woman who was now standing beside them, "Logan Huntzberger, nice to meet you."
"Oh, hi, I'm…Rory Gilmore. I'm just here with my grandparents tonight. They found out I had no Thanksgiving plans and insisted that I join them."
"Can you believe that, Logan?" Emily wrapped her arm into Logan's, "no plans for Thanksgiving? Well, we just couldn't leave her home alone for the night, could we?"
"No, I'll bet you couldn't," Logan smirked, glad to see it wasn't just his family who pulled this kind of crap.
"So I called your mother a couple of days ago, and you know your mother, of course she was more than happy to accommodate us when I explained how my beautiful, granddaughter, a New York Times reporter I might add was going to be home alone on Thanksgiving. Rory even joked about just ordering a pizza!"
"The Times," Logan gave her a glance, "impressive."
"Features," Rory told him.
"Our Rory has had quite a few bylines this year," Emily boasted as Rory wished the ground would swallow her up. This kind of attention had made her uncomfortable as a teenager and it hadn't gotten any better as she got older. She was never one to take a compliment.
The four of them walked into the foyer and Rory excused herself quickly to the powder room after she gave her jacket to the coatcheck, Logan for his part had disappeared back inside the room full of people while Emily and Richard made their presence known to Shira and Mitchum Huntzberger. Rory exhaled and looked at her appearance. Her grandmother hadn't told her they were going to Mitchum Huntzberger's house, arguably one of the most influential players in her business, she certainly hadn't expected the first person she would meet to be Logan Huntzberger, heir to the empire and much better looking in person than he was in photos she had seen, if that was even possible. She was glad that she had managed to find an appropriate dress in her closet, the cost of living in Manhattan was outrageous, and she wasn't in the market to buy a new dress on top of that, so she had pulled out an Alice + Olivia dress that her grandmother had gifted her the year before, she had only worn it twice, it had a high mock neck and cut just to her knee. Rory smoothed her dress and fixed her hair, reapplying her lipstick before heading back out to find herself a drink. "Gin and tonic, please," Rory smiled at the bartender.
"I don't think I've seen you at one of these things before, in fact, I'm not sure I knew Richard and Emily and a granddaughter?" the blonde haired man appeared beside her once more.
"Well they keep me hidden most of the time," Rory smiled at the bartender as she accepted her drink and took a small sip, "I'm not normally in Hartford for Thanksgiving. I was actually coming home to visit my Mom, but the joke was on me because she and my Dad decided to go on a vacation…a second honeymoon or something, I don't know, but here I am being dragged to a party with my grandparents like the girl who had to take her third cousin to prom because no one else wanted to go with her."
Logan grinned, it was a lopsided smirk really, "you didn't really take your third cousin to prom, did you?"
Rory laughed, "is that what you got from my pitiful story? No, I did not take my third cousin to prom, I'm not even sure I have a third cousin."
Logan scanned the room, he saw his mother and father talking to an old business acquaintance, he saw his sister scolding one of her three children and threatening to call Santa Claus, and he saw a sea of middle aged men and women who he had absolutely no interest in talking to. "Well, I'm glad to hear that this isn't your first choice for tonight. I would be alarmed if someone like you wanted to spend your night with this crew," he used his drink to gesture to the crowd.
"Someone like me?" Rory raised an eyebrow and smirked.
"Well, you're decent looking, you have a good job, you seem to be able to string sentences together. If I heard correctly, you ordered a gin and tonic, and while not my poison is much better than alternatives such as a strawberry daiquiri or a polar bear shot, which trust me, I have seen ordered by many a woman at a party in this house."
"Well, you certainly like to make assumptions, don't you?" Rory scoffed ever so slightly, "and I appreciate the compliment, decent looking, I really don't hear that as much as I would like…so if you'll excuse me, I'm going to go find my grandpa, and at least I know he won't be trying to marry me off while I'm here, and I will get in my car and leave after an appropriate amount of time has passed. Grandma said this isn't a sit down event…that is true, right? No one will notice me if I slip out?"
"I wouldn't say no one would notice," Logan countered. He wasn't used to this. This woman, Rory Gilmore, didn't seem remotely interested in him, if anything, she seemed annoyed by him, which was odd because more often than not it was him who was annoyed having to listen to women at these parties talk. He supposed these women weren't entirely to blame, they would have been told that they had a chance with Logan Huntzberger. The problem however, was that no one really had a chance with Logan Huntzberger, because the last thing that he was interested in was dating a woman who his parents approved of.
"Did you go to Yale? Richard and Emily are both Eli's."
Rory shook her head, "I didn't. I assume you did?"
"I did," Logan nodded, "I had a legacy to uphold."
"You seem to be managing."
"You don't like me, do you?"
"I don't know you."
"So get to know me?" Logan countered.
"Nice meeting you, Logan was it?" and off she went, Rory left her glass on the bar and walked away to chat with her grandfather. She spent the next hour and a half laughing and chatting with her grandparents, being introduced to a few friends and colleagues and after she had made it through an appropriate amount of mingling she told her grandmother that she was going to head back to Manhattan. She would drive her black Lexus IS 300 back to Manhattan and park it where it would sit probably until Christmas when she came back to Hartford to visit with her family again. Richard had tried to encourage her to spend the night in town, he worried, of course, about his granddaughter driving back so late at night, but Rory had assured him, she had one drink when she got there and had been drinking Coke ever since, she would call them when she was safely in her apartment. She said her goodbyes and headed towards the exit. Rory almost didn't notice him, noticing her, as she made her way to the coat check, "are you lost?" Rory asked absently as she was handed her black pea coat, she had bought it at Old Navy the year before and it was definitely not something she thought she would ever wear to a party like this, but like the dress, she was working with what she had.
"Am I lost?" he repeated with a smirk, "I grew up here."
"So you're just stalking me?"
"I came to say goodbye."
"How kind," Rory retorted quickly. "It was wonderful meeting you today, I hope you enjoy your holidays, and maybe I'll catch you at a funeral one day."
"Harsh," Logan put a hand on his chest dramatically. "But here," he handed her a business card.
"What am I supposed to do with this?" she held it up as she buttoned up her coat.
"After my parents saw us together…no one bothered me… no one introduced me to someone else…no one told me I just had to meet their daughter, or granddaughter as the case may be."
"How nice for you?" Rory slipped the card into her clutch and walked towards the door, Logan followed a few steps behind.
"I'm just saying. You seem nice, you're certainly easy to talk to…and seemingly my parents will leave me alone if they think I'm talking to you."
"And…?"
"I just think maybe we could both benefit from that."
"What makes you think I don't have a boyfriend?"
"You don't seem like the kind of girl who would have come here tonight if you had a boyfriend."
Rory nodded, "and what kind of girl do I seem like?" she bought herself some time, she didn't want to discuss her personal life. Four weeks prior, she did have a boyfriend. She had been dating Jess for three years when he broke up with her. They had first dated in high school, but that hadn't worked out. They had bumped into each other in Manhattan on Labour Day three years earlier and they had begun dating a few weeks later. Four weeks prior to this fateful evening though, Jess had unceremoniously dumped her and moved his things out of the apartment that she had been living in for five years. He had lived there for about two, and she couldn't help but notice after he left that even though he took everything he owned, the place didn't look any different. But she supposed the truth was, Jess had brought a few books and the clothes on his back when they moved in together, it wasn't as though he had a Picasso to take with him. He had moved back to Brooklyn, he had hated Manhattan, he had hated the doorman in the building, he had hated the elevator ride and the ultra modern finishes that he had deemed to be too rich for his blood. The truth was, Rory paid rent, but it didn't matter. Her father had bought the apartment and rented it to her, she knew as well as anyone that he was just putting the money aside for her to have later, but she still felt better believing that she was paying her own way. If she didn't make her payment, he wouldn't care, but she hadn't missed a payment yet.
"You look like the kind of girl who wouldn't be at a party like this without her boyfriend if she had one. Anyway, whatever. Humour me. I have the HPG Christmas party in a few weeks and I need a suitable date. Come with me."
"I don't know anything about you."
"You know your grandma likes me, so at the very least I think it would be fair to say I'm not an axe murderer. You almost know, or at least you should by now, that I'm persistent, and I won't try to sleep with you."
"Yes, because I am after all, decent looking, right?"
"Might not've been my best choice of words," Logan shoved his hands on his pocket and rocked back and forth on his heels, "think about it, my personal cell is on there. Text me, call me, e-mail me."
"Don't hold your breath."
