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History Repeats Itself

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note: first jess one-shot!!! (and i'm actually proud of it???) also i say their baby is one but i don't know babies to well so if she's too advanced for a one year old, just cut me some slack

warnings: teen pregnancy, food/eating

word count: 4.7 k

♡ summary: Being a teen mom is hard but without any help it's even harder, after saving up enough she can finally move to Stars Hollow to be closer to her baby's father

♡ Jess Mariano x reader

request ✓

The bus ride down was long, and it only got worse as 1-year-old Caroline woke up from her nap and decided to let everyone know of the inconvenience. Finally after the long months of working and saving up she had enough to move to Stars Hollow, unlike Jess who had a parent to send them and an uncle to stay with, she saved up and made it happen. She wanted Caroline to be around her father, and she wanted to be close to Jess.

And Y/n’s always loved the idea of a small town, a place where you felt safe, a place she would feel safe raising her child in, a place that wasn’t $2,500 a month for a closet. Here she could give her daughter a lot more, here she would have a support system in Jess and Luke. Unlike what her parents would give her.

By this point in the bus route it was only the mother and daughter and a couple strays, she saw the messy haired boy sitting on a park bench close to the bus stop, of course he had his nose in a book. She started packing up Caroline’s stuff, tucking her blanket and toys in the basket of the stroller.

When she got to the bus doors, Jess quickly made his way to help her lift the stroller down the steps, when the stroller was once again on the ground Jess squats down getting face to face with his little girl, “Hey, Care!” “Daddy!” He lifted her up by her armpits. When the little girl was out of her seat and in her dad’s arms, her mom stacked their bags on the seat.

“Hi! You’re so big! Really she is. She’s growing up so fast.” “Well she can walk way more stable now. No more scaring, mommy that you’ll fall if I look away for a second.” She says the last sentence in baby voice while she tickles the girl’s belly to make her giggle and their foreheads to rest on each other’s.

“So you gonna show us around?!” “‘Around’?” They continued their walk around the gazebo area, walking towards Luke’s.

“This is it, that's the record shop, that’s the bookstore, that's Luke’s, and that’s all you need to know.” “Well where’s the bank, I might need to rob it later.” “You’ll find a job. And if you don’t then work at Luke’s, he could do with the time off then maybe he’d get off everyone’s backs.” “He’s probably stressed with you always causing trouble.” “Me? Trouble? Nooo, I’m a peach.”

Jess had the baby today since Y/n was off to find a job, her first stop was the most promising. Luke let her know that a friend of his needed extra staff at their Inn for an event that was coming up, someone who could be an assistant of sorts. So after wearing her most capable looking top, and best fitting jeans. She kissed Caroline’s check and yelled goodbye to Luke and Jess as she began her walk.

When she walked inside she saw a man at the front desk on the phone. Waiting to ask for directions, she hung around the man’s desk, busying herself with some pamphlet. She couldn't help but listen to the man’s angry English in his french accent.

Suddenly he hung up the phone and got back to writing whatever he was writing, without looking up and with an annoyed tone said, “Yes?” “I was looking for Lorelei, I’m here for-” “The assistant job, yes.. Follow me.” He walked quickly to wherever it was they were going, mumbling along the way, “Of course, an assistant. Just what we need around here. Not like I don’t already do most of the work around here.”

He opened the door for them, it ended up being the kitchen they were now in. A tall woman holding a to-go coffee cup that said ‘Luke’s’ on it and a shorter woman in an apron fighting with a scruffy man about vegetables, which look to be parsnips.

“The mini-you is here.” “One little comment, Micheal. I’m not saying you’re incapable. I just want more help with organising events so I focus on planning!” “Whatever.” Turning on his heels, Micheal walked out the doors making his way back to his desk.

“So you’ve met Micheal! Sorry, we usually don’t let him around the new people but we're a little short-staffed. Let’s head to the dining room.”

They sat down at a table in the dining room, Lorelei asked all the important questions, and Y/n was perfect, now she was just asking the things she’ll tell Sookie later when the woman asks about the new hire.

Taking a sip of her sixth coffee this morning Lorelei asked, “So, are you new to town? I haven’t seen you around before.” The girl was stirring milk into her second coffee as she responded, “Yeah, I am. I just moved here with my um- my daughter, closer to her dad so…”

Since it was of course the time most adults got horrified, thought she was a bad kid, and though she didn’t get that vibe from Lorelei, it was at least bound to shock her. “You’re daughter? How old are you? Wait- I know, it’s on your resume. I mean- I’m, deja vu y’know? Abba did say ‘the history books on the shelf are always repeating themselves’.”

She must have seen the confused look on the young girl and explained, “I had my daughter when I was sixteen.. And came here to get a job, so just getting major deja vu. Well then, since I know what you’re going through, I won’t put you through the short mental torture of waiting for a call I was gonna do and just tell you you got the job.” “Oh, thank you! I really need this, I can’t thank you enough.” “Just change her name to Lorelei and we’ll call it even.” “deal.” Those two would get along great, much to Luke’s misfortune.

Y/n sat at the counter with Caroline in front of her sitting on the counter while she played with her mother’s hair. Jess was filling up cups of coffee and serving customers while he listened to Y/n’s words.

“So until you go back to school, you’ll have Caroline during the day here and when I’m done work I’ll take her.” “No, you’ll never have a break. After work you go to your house, relax then grab her after dinner.”

Jess may have this ‘I only care about myself’ attitude but that never included Caroline and Y/n, he’d kill for either of them at any given moment. He always put them first. If thought Y/n needed a break, she was getting a break whether she wanted it or not.

Just as the girl was going to thank him she was interrupted by another girl around their age coming to sit down at the counter, two over from her.

“I have the book you lent me.” She said, unknowingly interrupting the conversation since Jess was facing the coffee machine to make a new batch when she sat down. “Oh, thanks.” He muttered, notably not turning to face her.

On the inside Jess felt guilty. Why did he feel guilty? He didn’t do anything, he and Y/n weren’t together, nevermind the fact that all he did was lend Rory a book. As friends. Because they’re friends. But nonetheless it almost felt like cheating. Jess and Y/n may not be together officially but that didn’t mean that they both didn’t love each other. And not just because they were the parents to a beautiful little girl. Jess had always wanted more, he’d let the girl know that more than a handful of times, and she let him know it wasn’t unrequited, yet something always came between them.

You’d think having a baby together would bring them closer, and in some ways it did; they trusted each other more. But they also fought more and being the dumb teenagers they were, they didn’t have the emotional ability to move past that and build the relationship they both wanted. And then when they felt they were ready to, Jess was sent to live with his uncle. Just another fork in the road. But now they were living in the same town and had a good system, and people to support them. It was the perfect time, everything was going right, they could feel all the feelings that never really left resurfacing.

“Okay, I have to get to work. You’ve got her?” “Yeah.” “Bye, baby, I love you. I’ll see you in a little bit, but you get to spend all day with daddy.” “Bye-bye, mommy!”

She said bye to Jess after she walked around the counter and handed him Caroline, muttering a small ‘go see, daddy’ that Rory most definitely heard.

When the door finally chimed shut Rory shot up to follow Jess to the table he was now setting Caroline up at. She watched his gentle movements as he readjusts her shirt and places crayons and paper in front of her, which she got right into scriballing away.

“She’s yours?” “Yeah.” “.. So that girl is your girlfri-" "I’ve got work to do.”

The warm atmosphere of the dinner is a stark contrast to the cold winter air. Noticing Jess and Caroline are nowhere to be seen she assumes they were upstairs and makes her way up the stairs. Half-way up the flight of stairs she could hear her little girl’s loud giggles. She quietly opens the door to see Jess holding Caroline above his head, as if she was flying.

When she first got pregnant everyone told her Jess wouldn’t be a good dad, that she can’t rely on him for anything. God were they wrong. She doesn’t think it’s possible for her baby to have a better person as a dad. She sadly doesn’t get to watch the scene for much longer as she’s spotted by little Caroline.

“Mommy! I see daddy ‘morrow?” “Yes, you get to be with daddy all day tomorrow too.” “Yay!”

As the conversation between them goes on, Jess lets his little girl plant her feet back on the ground and starts collecting some things she’ll need during the night before she comes back here tomorrow, he then starts getting Caroline’s shoes on her feet. While Y/n sits on the couch next to their little girl.

“So who was that girl this morning?” “Who?”

Jess always did this, it was a tell tale sign that he didn’t want to talk about it, but that’s never stopped Y/n before. “You know who.” Of course having to be difficult, Jess gives her a fake confused look, as if he’s never met another girl in his life.

“The one returning your book.” “Oh, that girl.” “Yeah, that girl.” “She’s nobody.” “So you just lend books to ‘nobody’s now?” “Care, where’s Mr.Wiggle?” The girl lets out a gasp and reaches out for Jess to help her off the couch, when he does she runs into the closet where she previously hid while playing hide and seek a couple hours earlier.

“What? Don’t want Care to hear about her new step-mom?” “Don’t call her that.” “What? Care? Only you can call her that?” “No, don’t call Rory Care’s ‘step-mom’.” “Rory! I get her name!”

Jess was a quiet guy, but not this quiet, especially not with Y/n. He didn’t want to talk about Rory, maybe because it was weird talking about another girl with your baby momma. And yes it was weird for Y/n too, but for a completely different reason, she assumes. She liked Jess, and has since before she even knew about Caroline.

“C’mon, Jess, it’s me. I want you to be happy.” Sure Rory made him happy, but only because she was the only friend he had here, it wasn’t the way Y/n made him happy. Before he could deny for words again Caroline came back running into the room with her stuffie in her hands. Having already said her goodbyes, she opened the door and walked out.

“Caroline, wait hun! I think you should go for it Jess.”

She walked out the door, closing it behind her, leaving Jess to stare at where she disappeared. He decided to take her advice, just maybe not the way she meant it

Y/n helped Caroline pack more snow onto their snowman. Caroline wanted to do it after she heard Luke complaining about town events again, he stopped complaining when he saw how excited the girl was. They had Mr.Wiggles off the side learning against the tree, using him as a reference.

“Mommy, no. Mr.Wiggles has more hair.”

Caroline was getting very comfortable ordering her mother around, but in this instance Y/n let it slide, poking more sticks on the top of the snowman’s head to mimic Mr.Wiggle’s spiky hair.

“That’s good!”

Lorelei and Rory were just one snowman down, both told Caroline they thought she would win and encouraged her before she even started. Since they were so close, they could hear the scene that had just played out.

“Tough age, wait till you get to the terrible twos. ‘No’ is all you’ll hear.” Lorelei said, kindly as her and her own daughter walked past them. Y/n let out a laugh at the comment before she asks, “You guys done already?” “No, but after Michelangelo over there busted out the power buffer, and when Caroline busts out her cuteness, what chance do we have?” “I see your point.” “So off to Luke’s we go.” “We’ll see you there in a bit.”

Y/n was standing talking to one of the decorators when she saw Lorelei and Sookie step out of the kitchen, quickly finishing her directions she wrote down a note on her clipboard then made her way to meet them at the entrance of the dining room.

When Sookie sees her, she asks, “What’re we looking at today?” Sookie was really fun to work with, like Lorelei she was very chill as a boss, but Sookie was also so kind and always took it upon herself to make sure Y/n has eaten and that her and Caroline are taken care of. She could tell the woman was going to make an amazing mother.

“This is last on the list.” She replied, after she took a quick glance at her clipboard, then continued, “We’ve got trumpets, the madrigal singers-” “Sorry to interrupt, but I’m not playing squire of Bracebridge.”

Sookie and Lorelei must have finally told Jackson to play the squire, they told her earlier in the week that they were playing to ask at the last moments so he had to. It was a flawless plan, especially when Jackson can’t say no to Sookie.

She saw that Lorelei and Sookie were just ignoring him, so she played along and continued down her list, “All the servers are lined up. This is just for the recorder players and harpists.” She stopped at the recorder players and let Lorelei talk to them, ��Hi. Lay some on us, guys.”

The two recorder players played the soft tube they were going to come accustomed to in the next few days. The three of them shared positive looks and when their playing came to an end, Sookie said, “Hey, you cats really know how to blow those things.” Lorelei continued Sookie’s comment by saying, “You’ve got the gig. Y/n here will call you later with the details. Thanks.”

Recorder players started packing their things, Jackson started again on the fact that he wouldn’t play the squire, and the three women continued to ignore him.

“When do the quests arrive?” “Thursday at four on their own jet.” “After buying out the whole inn.”

“Must be nice to have money.” Y/n added, checking off and writing down more notes on her clipboard.

“You know what struck me today?” “-Was it the fact that I am not the squire?-""We’re crazy for doing this.” “We’re beyond crazy.” It did feel crazy, Lorelei told her they’d never done a function this big before and that’s the reason they hired more help. Like her, but also that they were planning to do a lot more big things like this, more weddings, and such.

“We’re ‘Anne Heche speaking her secret language to god and looking for the spaceship in Fresno’ kinda crazy.” “Oquinis no-goodo noto.” Sookie said, causing Y/n add, “Il ecnatra dos guidan.”

Their nonsense was once again interrupted by Jackson, “And spring this on me at the last minute too. I mean, that’s just manipulative.” Suddenly a cook pops his head out of the kitchen, saying calmly, “Sookie- fire!”

Sookie rolled her eyes softly, this happened far too often, before saying, “I gotta get back in the kitchen. You guys handle the harps?” Both women nodded and replied in unison, “You got it.”

“Alright. I’ll do it. I’ll play squire Bracebridge if that’s what you want.” Everyone knew he would cave eventually. Sookie patted his arm and said a quick, “Thanks, sweetie.” before walking back into the kitchen to hopefully deal with the fire. “As long as it’s not just because I fit the costume.” Jackson looked back at Lorelei and Y/n, Lorelei had a grin on her face while Y/n wore a tight-lipped smile. “It’s because I fit the costume, isn’t it?” He followed after Sookie.

Lorelei put her arm around Y/n and led them to the harpist, “Go ahead.” The harpist played the same tune as the two recorder players. But just as the woman started, Lorelei got a call. She patted Y/n’s arm, “I have to take this, you handle the harpist.”

The girl tried to stay calm, nodding her head and going back to listening to the music. Lorelei trusted her, yes it wasn’t a big job by any means, but still it was a step into a bigger role down the line.

The next day, Sookie and Y/n had all the waiters/performers in the dining room going over what their job was. And teaching them the old English words to use for things.

Sookie was just telling Rune that he couldn’t just talk like an old man whe Lorelei came in with a disappointed look on her face, and let them know the dinner was off.

The three women, as well as Rory and Caroline were now sitting at a table at Luke’s, Caroline was happily eating her pancakes, plain just as she liked and completely unaware of the collective disappointment of the group.

Lorelei has really welcomed Y/n into her life. She may not be Jess’s biggest fan, but she would always help another teen mom out. Especially since she sees so much of herself in Y/n. She’s grown to really love the girl in the short time they’ve known each other. And aftering hearing Y/n didn’t have her family in her life she was more than happy to help and maybe become that family for her one day. Just like Mia did for her.

“I’ve got 30 pounds of aged beef, trays and trays of trout, mountains of prune tarts. I diced pumpkins until my hands turned orange. I’ve got pumpkin hands!” Sookie showed the table her hands, it apparently caught Caroline’s attention since she grabbed Sookie’s right hand and held it in her left while she continued eating. Sookie lets her hand rest in the little girl’s while she freaks out more and asks Lorelei, “How can you stay so calm?” “There’s nothing we can do about it.”

Rory was just as upset, mostly because she knew how hard her mother worked on the planning, “I can’t believe they got snowed in.” Y/n hasn’t told Jess, but she’s become pretty close to Rory, the girl sometimes comes to the Inn and helps around and Rory’s become kinda her only friend, that was until Rory invited her to the record store with Lane. After that day she had two friends.

After knowing Rory more, she realised how much she and Jess have in common, and even though Rory has a boyfriend she can tell there’s an attraction to Jess she’s trying so hard to hide.

Y/n zoned out for a moment, looking outside, she was upset that the first event she helped organise wouldn’t even happen. She was broken from her stare out the window from Caroline jumping in place while sitting on her mom’s lap, the cause of which was Luke coming to the table.

“You girls want anything besides coffee?” He asked, adding on with a pat on the girl’s head, “Or pancakes?” “Hey, what about Luke?” “What about him?” “He eats, and Jess eats. Doesn’t Jess eat?” Sookie directs the question at Y/n, before the girl could say anything Luke cuts her off, “What’s she doing?” “I think she’s inviting you for dinner.”

Getting distracted while trying to convince Luke to come to dinner, the four decide to still put on the dinner for the town. Like an out of control slumber-party.

The dinner was going great, the secret amazing part of inviting the town was that Y/n and Caroline could actually meet everyone. Miss. Patty and Babette loved Y/n and Caroline (mostly Caroline), Caroline loved Kirk, and everyone loved that Caroline could do whatever she wanted and Talor wouldn’t say anything. And Y/n got to meet Paris after all the stories she’s heard.

Caroline and Y/n were in line for the horse drawn carriage rides, when Caroline saw her favourite person, Lane. “Laney! I ride with you!” Lane, before agreeing, made eye contact with Y/n to make sure it was okay. Y/n gave them the go ahead and helped Caroline get settled. After their carriage left she made her way to the next one. Telling the driver it’s just her.

It was nice to get a break from everything. It was quiet and peaceful. Well that was until Jess ran up and hopped on the carriage next to her. Without a word he put the blanket that was over the girl’s legs on his too.

“I thought you and Care were going together.” “She’s one ahead, with Lane.” “Ahhh. Well it’s two to a sleigh no more, no less. So you were breaking the rules, you're welcome for saving you.” “You could have hurt yourself.” “Aw, you care about me.” “You are my baby's father.”

She wished she just agreed with him. She didn’t just care for him because he was Caroline’s dad, and she doesn’t think she says it enough. But then again, maybe it would mess things up if she admitted that. But that decision was made for her.

“I’m touched.” “Jess. I don’t mean it like that. I care about you, Caroline or not.”

Trying to change the topic to something she thought was more lighthearted, she says, “So, how are things with Rory?” “There are no things with Rory.” “C’mon, Jess, we can talk about this stuff-” “Why are you so insistent that I date Rory?”

She wasn’t expecting that outburst. Not from Jess. He rarely ever yelled at her, and when he did it was always misplaced anger, never actually angry at her. This time it was her, it was what she said.

“I just want you to be happy-” “C’mon, Y/n. Be serious.” “I am. I want-” “If you want me to be happy so bad, why won’t you give me a chance?!”

He turned his face to her, looking right into her eyes, she could see the hurt in his. Did she put it there?

“What’re you-” “Since we found out about Caroline, I’ve tried and tried to help you realise that I love you. And not how you mean ‘I love you’. I don’t love and care for you because we have a family and I have to. I love you, because I want to. I want to be with you. And I know it will be hard, but I’ll do the work.”

If she had more social awareness at the pent she would have hated that the coachman heard all of that. But after what Jess said, the look in his eyes; that was so full of love. She felt like it was just them two in the world. No, that it was just their little family in the whole world. He and Caroline were all she would ever need.

“I love you too, Jess. I have for so long, long before Caroline, but I thought you wouldn’t want to be tied down to me, especially after I had Caroline, that any sign I thought you gave me was all in my head.” “It’s not.”

He brought her in closer to him, an arm around her shoulders and when her arms wrapped around his waist he left a kiss on the crown of her head. The small kiss brought her eyes up to him, which led to their first real kiss in one year and nine months.

His lips were softer than she remembered, but they still fit into hers as if they never left.

She broke away from their reuniting kiss to place her head in the crook of his neck, wanting nothing more than to be close to him.

“My mom didn’t want me to come home.” She took her head out of his neck to look at him fully. They were always that person for each other, the one you can tell your problem to and they knew when to help and when listening was enough. Right now, she knew listening was enough.

“I’m sorry, Jess.” “It’s fine. Just sucks.” “I know. Well, Care and I will always want you to come home.” After her words, he brought her closer than before. She was always just what he needed.

Wanting to change the subject, Jess nodded his head to the snowman Y/n and Caroline built. “It’s good.” “What?” “Your snowman, well Caroline’s snowman I'm sure she’d want me to say.” “You know which one’s ours?” “Definitely shows her personality… It kinda looks like Mr.Wiggles.” “That’s what we were going for. But everyone thinks the one on the end is going to win.” “Really? It’s so overdone.” “I agree.” “You and Care’s should win.” “Agree again.”

The dinner was filled with Jess and Luke confused at what exactly was in the food, Jess and Y/n trying their best to keep Caroline sat which about half an hour in they gave up and just let her walk around the lobby, as well as saying hello and talking to everyone at the table. Having an interesting conversation with Mrs.Kim about grace, ‘helping’ Kirk by sitting on his rolling food cart, and even talking with Paris for a while.

Overall it was a great night. Even better when Jess, Y/n, and Caroline got to their shared room, putting Caroline asleep together for the first time in a while. And falling to sleep in the same bed together, holding each other, listening to each other’s breaths, as well as Caroline’s. Everything was just how they both always secretly wanted. And now get to have openly and freely.

In the morning Y/n got up early since she was technically working, and she still was when Luke, Jess, and Caroline left to open the diner for the day. It was around noon when Y/n finally left, walking to Luke’s to spend the day with her two favourite people. Which was when she saw Michelangelo’s snowman fallen to a large pile of snow on the ground.

She didn’t even have to think for a second to know that Jess did it. Sometimes he did the weirdest things to show his love.

The bell rang as she pushed open the door, she sat down next to Caroline, saying ‘good morning’ and getting one back before she made her way to the counter.

“I saw what you did.” “What’d I do?” “Caroline will be happy she won.” “Anything if my girl’s win.”

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