AN: Thank you, as always for the reviews, they are so fun to read and I do love messaging back and forth. We have a bit of progress here, kind of... but please remember, the goal of this story is not to have them together by the fourth of July. They are going to pine and piss each other off along the way. I actually finished this chapter last night, and then wrote the Amelia Lane chapter that I just posted, so this now means it is time to write more of The Holidate. Easter is coming next

Disclaimer: I do not own Gilmore Girls or The Holidate

Part Four - February

February 11, 2021

Rory was sitting in the offices of one Kate Edmonds wishing she was just about anywhere else as her best friend, Abigail, leafed through wedding invitations. Rory wasn't sure what the rush was, but apparently Abigail wanted to get married in the Hamptons, and it had to be this year. Rory smiled and nodded, her only real commentary was the fact that one of the fonts wasn't very readable, but beyond that, she just smiled, nodded and encouraged her friend. She was after all, thankful, thankful that Kate had agreed to let the bridesmaids wear black, which was a small miracle given that originally she had hoped they would all be in yellow which was not Rory's colour. They had discussed colour schemes, menus, they had opted against a save the date given how soon the wedding would be and instead they would aim to get the invitations out in late April or early May. Kate, the wedding planner had advised that they should block of a bunch of rental properties or hotel rooms with refundable deposits in order to secure locations for their friends to sleep and to say that Rory had zoned out at this point was an understatement. She was happy for Abigail, she really was. She was happy to go dress shopping, and look at venues, taste booze or food or cake, but she wasn't particularly interested in the minutia of picking linens and invitations which seemed to be how this particular meeting was going.

Rory felt her phone vibrating in her purse and without even looking, she excused herself and put it to her ear, "Rory Gilmore," she answered quickly.

"Logan Huntzberger," his voice was warm in her ears and without even meaning to, Rory smiled.

"Logan, hey."

"Hey yourself, Ace," Logan smiled into the phone, he was sitting in his office reading over some financial reports for the company, "how've you been, I haven't heard from you since our lunch…"

"I know, I'm sorry," Rory told him as she stood in the sterile hallway, "I've just been really busy with helping Abs with wedding stuff. I know they just got engaged, but they've decided to get married in the summer, so it's just been super chaotic."

"I know, Nick told me, pretty wild."

"Nick told you?" Rory repeated, she was leaning against the wall now, her free hand running through her hair.

"Yeah we have hung out a few times with the boys since New Years, fun guy."

"The best," Rory agreed. "So uh… what can I do for you today Logan?"

"Wanted to see what you were up to Sunday?"

"Sunday?" Rory repeated, "isn't that…"

"Yes."

"Well, if you must know, I was planning on buying some chocolate, some cookie dough ice cream, and ordering enough takeout for a family of five, and watching movies that my mom would mock me endlessly if she knew I watched…"

"Wow, that almost sounds like you're looking forward to that?"

"I am," Rory shrugged her shoulders even though he couldn't see her. "Do you have a party or something?"

"No," he admitted, "I just thought if neither of us were doing anything…"

"If you want to come over, come over," Rory told him nonchalantly.

"You sure, I wouldn't want to crash your big plans…"

"We're friends, or whatever, right? So if you have people who think we're dating, then come over and you won't be lying when you say you spent the night on the couch with me."

"Can I bring the food at least?"

"I'll order it, you can pick it up. I'll text you the details. No later than five, k?"

"If you insist, don't go too crazy with Abigail, Ace."

"You're too kind," Rory rolled her eyes and hung up before heading back into the office, relieved when she saw they seemed to have moved on from invitations.

"Who was that?" Abigail asked.

"Logan."

"Huntzberger?"

Rory nodded her head in response and it wasn't lost on her when she saw Kate's head perk up. "We're going to hang out on the weekend."

"You and Logan are going to hang out on the weekend," Abigail repeated, "where?"

"Just at my place," Rory shrugged, "it isn't a big deal."

"Sure," Abigail nodded, "so do you think we should do cake or cupcakes or both?"

"Both," Rory told her, "but we're not like…deciding that today. Right?"

"No," Abigail assured her, "just making a plan for the room. So what is the deal?" she asked, "with you and Logan."

"What deal?" Rory shrugged, "we're friends. We hang out sometimes and sometimes we do events together."

"And that is it?"

"That is it," Rory nodded. "He's not interested in me, I'm not interested in him. He doesn't find me attractive, he is very attractive."

"Well I'm glad you're not blind," Abigail laughed. "How long has it been anyway?"

"Has what been?"

"Since you…"

"Since I what…"

"Since you had sex," Abigail whispered loudly.

"Abigail!"

"Oh come on Rory, it's not healthy. Can that thing close up from lack of use?"

"You are being crass," Rory rolled her eyes. She imagined that if her own mother didn't think she was dating Logan, Lorelai would have asked a similar question by now. "It hasn't been that long."

"How long."

"Since Jess," she admitted.

"Ok, so what, you did it and he broke up with you two days later or…"

"Abigail!"

"Rory, you need to lighten up, it is just sex. Everyone has sex. I'm sure Kate here has sex too, don't you, Kate?" The wedding planner awkwardly shrugged her shoulders as Abigail continued her rampage, "Rory I'm just worried about you."

"Don't worry about me."

"Then tell me."

"You have to promise not to react, not to make a face, not to say a single word or else I will put blue dye in your shampoo or something!"

"I won't say a word."

"It's been since Labour Day," Rory exhaled and glared when she saw Abigail flinch ever so slightly, "don't!"

"I didn't!" Abigail countered quickly, "well…that is…fine…but what do you think about macarons? Do you think macarons, cupcakes and a cake are too much?"

"There is no such thing as too many sweets," Rory retorted, thankful that Abigail had kept her promise and not brought up her drought.

xxx

February 14, 2021

Rory was furious. Actually, furious may not have fully described her current mood. Of course Mr. I don't do Valentine's Day had texted her that morning and declared he needed to swing by and look for a USB drive that he couldn't find and needed for work. Rory, being Rory, didn't have the heart to say no to him, so instead she had texted Logan and asked him to come over earlier and bring a couple of sweatshirts, which he couldn't help but find odd. Logan had however, complied and he was knocking on her door a little before two that afternoon.

"Thank you," Rory pulled him into the building, "did you bring them?" she asked as she frantically grabbed the bag out of his hands.

"What the hell is going on, Ace?"

"He's coming over."

"Who is coming over?" he asked, she had managed to get the sweatshirts out of the bag and now he was following her to her bedroom.

"Jess! Jess is coming over because he can't find a USB drive and he thinks he left it here!"

"You guys broke up months ago, and he just realized he needs a USB drive today of all days?"

"Jess isn't a guy who does Hallmark holidays," Rory explained, "he probably doesn't realize what day it is, and he called wanting to come yesterday but I couldn't because I was out, and so I just casually said today without remembering, and now…here we are."

"So you want my clothes because…"

"Because I don't want to look like a pathetic loser who doesn't have sex with anyone," Rory was frantically tossing things around in a bedside table right now, "here, take these," she handed him three or four condoms.

"Look, Rory, respectfully…I don't need these."

"I know you don't, but if he goes in here looking for his stupid fucking USB drive, he will see that some are used and he won't think that the unopened box of condoms he left in October is still unused!"

"Alright, so we're off the deep end here," Logan exhaled as he took the sweater from Rory's hands, before she could protest he mussed up the bed so it looked like it hadn't been freshly made, and he absently tossed his sweater on the ground. "Out," he declared.

"This is my bedroom!"

"Out."

"Fine," Rory rolled her eyes and turned around.

Logan smiled as she left and he quickly removed his jeans and boxers, tossing them on the floor. When Rory had told him to bring his sweatshirts, he had over prepared and brought sweatpants as well, thinking that it was completely possible she just had a weird mandatory dress code for the evening, but she also would have known him well enough to know he wouldn't be caught dead wandering around Manhattan in sweatpants. "Come back," Logan called, he casually tossed his pants and boxers on the floor given that he was now wearing fresh bottoms and Rory smiled as she came back into the room.

"Thank you."

"It's what I'm here for," Logan shrugged. "Do you have any yoga pants or just like…comfortable shorts that maybe you sleep in sometimes?"

"Do you have a thing for crossdressing?"

Logan laughed and tossed a Yale t-shirt at her, "put this on, and put on a pair of pants or shorts that will drive him nuts."

"You're good at this."

"I have probably been on the receiving end of a scheme like this before," Logan laughed.

"Thank you," Rory blushed, "you must think I'm pathetic."

"You're a lot of things Ace, I know that much, but pathetic is not on that list."

Logan returned to the kitchen and opened the fridge, he could hear Rory moving around in her bedroom as he helped himself to a beer and searched her drawers for a bottle opener as he cracked the lid off of the long neck bottle of Stella Artois. He took a long sip and heard a knock on the door. "Ace?" he called, no answer. She must've gone into the washroom. Logan held the bottle in his right hand and walked to the doorway, swinging the door open to see a dark haired man standing in front of him, "hey."

"Rory here?"

"She's just in the bathroom," Logan moved to allow Jess access, "I'm Logan Huntzberger."

"Jess Mariano," he nodded as he walked into the kitchen. Logan followed, a smirk on his lips as they came to an awkward stop, "I just need my USB drive, I must've forgotten it when I moved out and I need it for work."

"Sure, just uh…chill here for a sec?" Logan told him as he put his beer down on the counter, "I'll go get Rory."

"Sure."

Logan disappeared down the short hall to the master bedroom and knocked quietly on the washroom door, "Ace?"

"One minute," Rory hissed, not knowing anyone else was there.

"He's here," Logan told her, his voice remaining in a whisper.

"He's here?" Rory swung the door open in a panic as she pulled his Yale t-shirt over her head, "how did he get in?"

"I let him?" Logan looked at her with a laugh. "You look good."

"I look good?" she looked down at herself, a ratty old t-shirt and a pair of overpriced Lululemon pants she hadn't done yoga in since she bought them.

Logan grinned and lowered his voice, moving his lips towards her ears, "you look like you've just been fucked senseless and you threw on some clothes in a rush. That is the goal, right?"

"That's the goal," Rory smiled, appreciating his help at this particular moment.

"Hold on," Logan saw that she had put lipstick on, he brought his thumb to her lips and began smudging it ever so slightly on her lips, "there you go, you've got this Ace."

Rory laughed as she left the bedroom and went to the kitchen where her ex boyfriend was now sitting on a barstool, "hey," she gave him half a smile.

"Hey," Jess stood up, "I uh…sorry."

"Oh, Logan?" Rory smiled, "no problem," she assured him. "So you said a USB? I looked around a bit, but where do you think it could be?"

"It's either in our," Jess fumbled for words, "sorry, your room, or in the other bedroom I think. Maybe the crap drawer?"

"For something so important you certainly have that nailed down," Rory rolled her eyes, "you go look, I'm going to have a drink."

"Sure."

Logan was exiting Rory's bedroom just as Jess was entering, the two men awkwardly shuffled at the door and Logan joined Rory in the kitchen, taking a sip of his beer as he did, "so that is Jess?"

"It is," Rory nodded.

"I see what you meant about rough around the edges," Logan told her, they could hear him opening and closing drawers, "he's good in there?"

"He's harmless," Rory assured him.

"Come here," Logan nodded, from his spot in the kitchen he had a view of the doors to both bedrooms and he watched as Jess moved to the guest room/ office and drawers again opened and closed. Rory complied and looked at him with confusion as Logan positioned her so that she was standing directly in front of him, "trust me?" he asked, she was facing him and she smiled and nodded her head in response. "Just wait," Logan put both of his hands on her shoulders as he listened to the sounds of footsteps, and just a few seconds before Jess left the bedroom, Logan pulled Rory towards him for a kiss. He could feel her freeze, just for a moment before her hands found his chest and his tangled in her hair. He waited a moment, until he knew that Jess would not only be standing right behind them, but also when he knew that Jess would have been forced to watch their little show for a moment to pull away slowly, placing a couple of soft kisses on her lips as he did. "Oh, man…hey, sorry, we got a little carried away there," Logan rubbed his lips as Rory turned to face Jess.

"Di…uh, sorry…did you find it?" Rory managed to ask as she took Logan's hint and leaned her body back against his.

"Guest room," Jess lifted a hand, "sorry for uh…interrupting your date."

"Oh this isn't the date," Logan gave him a smile, "first Valentine's and all, we're just getting started."

"I'll bet," Jess nodded, "Rory has never really been much of a Hallmark holiday kind of girl, have you, Ror?"

"Amazing what a fresh perspective will do," Logan winked at him.

"Alright," Rory moved away from Logan and took Jess by the arm, leading him towards the exit, "glad you got what you needed. I'm sure you have plans tonight, so…have a good night…"

"Yeah, you too," Jess paused for a moment after Rory had opened the door to let him out. "Really, Ror?"

"Really what?"

"That guy."

"Logan?"

"No, George Bush, yes, Logan." Jess shook his head and stared at her, "that is who you're with?"

"What do you care who I'm with Jess?" Rory rolled her eyes, "last I heard, you have a girlfriend and you're perfectly happy. So do me a favour and go. If I find anything else of yours, I will have it sent by courier. Don't come back here." She could see him open his mouth as she closed the door in front of him and locked it. She took a deep breath before returning to the kitchen where Logan had now grabbed his beer and moved to the couch. "What the hell was that about?"

"You're welcome…"

"You seriously thought that was a good idea?" Rory raised an eyebrow as she began opening and closing cupboards until she pulled out a wine glass and then pulled an open bottle of white from the fridge.

"I seriously thought that this was essentially what you asked me to come over early for was," Logan told her as he grabbed the television remote from the coffee table and turned on the TV. "Do you still want me to go pick up dinner or will they deliver?"

"I didn't ask you to come over to kiss me," Rory countered, "and certainly not like that!"

"I kept my tongue to myself, and my hands off your ass," Logan smirked, "look, I'm sorry. I thought the point here was to make Jess think that you had moved on. If I misread that situation, my apologies."

Rory exhaled and sat down on the opposite side of the couch so there was a full cushion in-between them. "Dinner will be here soon," she answered his previous question, "and I'm sorry for yelling. You did me a favour, and this shirt, aside from the fact that it is from Yale is really comfy."

Logan smirked as he pulled up an old episode of Dateline, "nothing says love like watching people who probably murdered their spouses or lover, right?" he asked her and she nodded her head in response, "and I'm not sure where else you expect my sweatsuits to come from if not my college days."

"I have an entire drawer full of Harvard stuff," Rory admitted.

"So how did that work out?" Logan asked, finishing off his beer as he kept his eyes focused on the television. "I'm surprised that you weren't at Yale. Your grandparents both went to Yale, your great grandparents…"

"I know, trust me, I heard a lot of that when I was deciding. I got in, at Yale but…I had always wanted Harvard, I don't even know how else to explain it. Since I was a little kid, all I wanted was to go to Harvard. My mom, she had wanted to go to Harvard, but she couldn't."

"Why not?"

"You really don't know anything about me, do you?" Rory laughed.

"I know what you've told me about yourself," Logan told her honestly, "but if you're asking if I have been sleuthing for information, then no, I don't know unless you've posted it on Instagram in the last couple months."

"My mom got pregnant when she was still in high school, she was sixteen. So she and my dad got married, and then until I was about one, we lived at my grandparents house. But then…one day I guess my parents just decided that was enough, and they left. They moved to this little town about half an hour from Hartford, and they rented a little shack that was on the property of an inn. My mom worked at the inn, and my dad worked and went to school at the same time to try to finish. He managed to go to college, so I think my grandparents helped him out, but I've never actually asked. My mom had wanted to go to Harvard, I remember her telling me when I was young. Not in a 'you must go to Harvard' way, but she wanted me to have options. So it became my dream. She gave up so much for me and my dad, the least I could do was fulfil the dream in the only way I could. So eventually she managed the inn, and my dad got a pretty good job working with my grandpa in insurance, they bought the house in Stars Hollow, things kind of levelled out with my grandma and grandpa and they helped when I got into Chilton. When it was time to apply to college, I applied to all of the schools you would expect, and I got into all of them. Harvard gave me a bit of financial aid, and it just…it was what I wanted. My grandpa was disappointed, but they came around. I see them as often as I can, and I know they are so proud of me…but going to Harvard was just something I wanted to do for my mom, and for me."

"So if you and your mom are so tight, why do you have to lie to her about having a boyfriend?"

Rory laughed, the way he said it made it sound so simple, but she knew it was nowhere near that simple. "It is way more complicated than that, but I think she just feels better thinking I'm not alone in Manhattan. I have my friends, I have my work…I'm perfectly happy, she just worries that I'm missing something."

"Did you tell her we had plans tonight?"

"I told her the truth."

"Which is?"

"That we were having dinner and hanging out," Rory stood up as the doorbell rang. She walked quickly to retrieve the Chinese food she had ordered and began spreading it on the counter. Logan joined a moment later and began searching the cupboards for plates which he quickly found and put two down beside the food while Rory got utensils out.

"This is just for us?" Logan looked at the pile of food.

"I'll eat it for a few days," Rory shrugged, "it's a Gilmore thing…or maybe a Hayden. I'm not actually sure, but this is what my parents used to do, well…they still do…"

"I don't think I've ever seen my parents eat Chinese food," Logan laughed as they began putting food on their plates, Rory gave him a horrified look. "I mean other than actual Chinese food, in China…but not this kind of Chinese food."

"They haven't lived."

"Are you telling me that you think Emily Gilmore has eaten a chicken ball with sweet and sour sauce, because if that has happened, I really wish there was photographic evidence."

Rory could appreciate where he was coming from because seeing Emily Gilmore eat like that was a rare occurrence, in fact it happened typically once a year. "There is a rule with my parents that for your birthday, you get your favourite food, or well, I get my favourite food. My mom sacrifices. So for my birthday, every year, my grandparents ordered Chinese from this fancy place in Hartford that is expensive enough that they are still Richard and Emily, but is also very traditional American Chinese food. So it comes, the maid plates it and they eat it…"

"But you said your mom sacrifices?"

"The trade off is that on her birthday, my grandma puts together a menu that she genuinely thinks is full of things my mom loves, but in fact, my mom doesn't really like fancy food, but she tolerates it so that I can have my yearly Chinese with them."

"How are the two things related? Why can't you have Chinese and your mom still have what she likes? Do you have birthdays a week apart or something?"

Rory laughed as they both made their way back to the couch, Logan having got another beer, and Rory brought the wine bottle out and topped up her glass. "No, I'm in October and my mom is in the spring, but it's just how her and my grandma work…if mom complained about the food my grandma would hear that she was complaining about all birthday food and everything would fall apart. It's a balancing act."

"Sounds almost as complicated as the Huntzberger circus."

"Did you have to tell your parents what your plans were for tonight?"

Logan laughed, "my Dad just asked that I not show up on Page Six, so I think I should be good. I was out last night with friends, but nothing salacious. My mom asked if I was seeing you and I kept it vague. I don't want to draw you into that mess by making this seem like a bigger deal than it is."

"I get that," Rory nodded. She was hesitant to bring Logan around her own family more than she needed to, even if it was to her benefit because they left her alone. They seemed to have hit a middle ground, she knew that Logan would be expected at major holidays, but she dismissed his absence on other weekend visits by simply saying they were keeping it casual or that he was busy with friends, work, family or all of the above.

"Which reminds me," Logan paused as he chewed his lo mein. "Are you free on Easter Sunday?"

Rory shrugged her shoulders, "I doubt I have plans…"

"Can you come to a thing with me?"

"A thing?" Rory repeated.

"My family goes to a brunch every year at Tumble Brook in Hartford," Logan referred to the country club where his parents had been members his entire life, they had gifted him membership when he turned eighteen, he wasn't sure if it was a joke or not, but fourteen years later, he still had his membership and a couple of times a year he played an obligatory round of golf with his father, and attended various events.

"Sure," Rory shrugged.

"That easy?"

"My family goes too," Rory explained, "two birds, one stone. Plus it would be awkward if I said no and then we saw each other there, don't you think?"

"So it is a not-date date."

xxx

"Let me get this straight," Finn Morgan sat in Logan's office despite being asked at least twice already to leave. "You spent most of the day, and into the wee hours of the morning with this girl, Reporter Girl, last night…and you didn't have sex? On Valentine's Day…"

"Correct."

"But on Saturday, you went home with…"

"I didn't go home with anyone on Saturday. I spent some time with Ashley, but that is all above board. Rory and I aren't dating. Rory and I see each other for mutual benefit at events."

"And you and Ashley…"

"Ashley and I saw each other for twenty minutes in her car, for mutual benefit," Logan laughed.

"And Reporter Girl is alright with that?"

"Rory and I aren't dating, Rory and I are just friends."

"Right…this makes no sense mate, and I'm not even drunk."

"You usually understand things better when you are drunk, Finn."

"Is she nice?"

"You've met her."

"Only briefly," Finn countered, "and it was new years, I met a lot of women."

"She is nice," Logan assured him. "She is smart, she has a good job, and she has absolutely no interest in me, which might be why I don't hate her company."

"Well that makes perfect sense?" Finn cocked an eyebrow at his friend.

"I just mean, whenever I meet someone, they're interested in my money or status or whatever. I haven't had a girlfriend since…"

"Laura," Finn sighed loudly. "I loved Laura."

"I know you loved Laura, I loved Laura too, but if you'll recall, Laura stopped loving me."

"I do remember, it was quite painful," Finn nodded as he thought of the girl who had broken up with Logan two or three years prior. "I think she had a baby with the guy she married though."

"How nice for her?" Logan rolled his eyes. "Anyway, I'm over Laura, but the only comparison is that Laura also wasn't interested in me because of who I was."

"But you're not interested in Reporter Girl?"

"Rory and I are friends."

"Right…because this is going to end well?"