Samantha Gilmore || A Gilmore...

By Roohoo88

74.9K 1.9K 279

What if Lorelai wasn't the great mother everyone thought she was? What if she left something behind with her... More

Season 1 cast :)
Prologue
Dinner & Drama
"I have no idea who that is"
The Club
Rory's 16th Birthday
Buffer
Rory's dance
Cross my heart
The Beginning of the End
Happy birthday to me
Waiting, waiting, waiting
The truth revealed
I spy with my little eye
Building bridges and breaking them
Season 2 Cast :)
Moving on
No second chances
Good news and bad news
New favorite person
Rumor has it
Kill em with kindness
Always in last place
I'm fine, she said like a liar
A Christmas Miracle
Like mother, like daughter
You're an idiot, Archie Brown
Never enough
A world alone
When the feeling sinks in

A Retired Richard

1K 34 5
By Roohoo88

Samantha Gilmore has spent nearly every waking hour with her grandfather for the past two weeks. What happened fourteen days ago, one may ask. Richard Gilmore retired. That is what happened and now he is very, very bored. This leads us to where the grandfather-granddaughter duo is now.

"Make sure you don't drop the snowcones," Samantha called over her shoulder as she and Richard maneuvered around several people's legs, trying to find a seat in the baseball stadium.

"Don't worry," Richard responded as he held the snowcones, foam fingers, and popcorn. "I've got everything."

"B17 and B18," Samantha read the number on the seats and then looked down at their tickets, "Papa I found them!"

"Wonderful," Richard handed his granddaughter her cherry snowcone before sitting down next to her, dumping all their things in front of them. Samantha grinned, adjusting her Boston Red Sox cap on her head so it was shielding the sun from her eyes. "Mhm," Richard hummed in delight as he took a bite of his blue raspberry snowcone. "This is quite good."

"I told you," Samantha teased before the speaker came on.

"On the visiting side we have Jared Carkuff playing for the Chicago Cubs," the sports announcer spoke, making the cub's side of the stadium roar with applause.

"Don't clap for him!" Samantha shoved her grandfather's hands back on his lap. "That's the opposing side."

"Oh," Richard let out, slightly startled. "So we aren't supposed to cheer for the other side?"

"Have you ever been to a baseball game?"

"Haha," Richard rolled his eyes before asking, "Who are we supposed to cheer for then?"

Samantha opened her mouth to answer but she was cut off by the announcer. "And on the home side, we have Ted Williams batting for the Boston Red Sox!"

"For them," Samantha nodded her head at the team coming out to the stadium before letting out a loud whoop, her grandfather doing the same.

~:~

Samantha cheered, holding her foam finger above her head, as Ted Williams came up to bat. "Hit me a foul ball, Teddy!"

"Samantha," Richard started as he looked at his granddaughter. "You do know the odds of him hitting you a foul ball are one in a million, right?"

"Yes," Samantha nodded. "But I choose to see the positive."

"Good for you," Richard grinned before leaning back in his seat. "We need more people in the world like you, Sam."

"Fingers crossed that my clone machine works," Samantha joked, making Richard give her a confused look. "I was just messing with you."

"Ah," Richard nodded, laughing. "I see now."

"Oh, here he goes," Samantha pointed at number nine, who was swinging his bat back and forth.

"Strike one!" the announcer declared, making Samantha and Richard let out a groan.

"Let's stand up," Samantha pulled her grandfather to his feet, "to see better."

"Good idea," Richard nodded before cringing. "Oh dear, that's strike two."

"Hit me a foul ball, Teddy!" Samantha shouted again, waving her hands in the air before adding, "But not too hard."

"Oh my goodness," Richard put a hand over his eyes to shield the sun as he saw a ball heading their way. "It's coming over here!"

"Oh," Samantha bounced up and down, "Papa give me a boost!"

Richard lifted his granddaughter up just in time for her to catch the baseball. Samantha raised her hands above her head in victory as she held the ball. "Whoo-hoo! Papa, I got my foul ball!"

"Well look at that," Ricard exclaimed as he put her down. "I guess you really are one in a million, Samantha."

"I guess I am."

~:~

"Whoo-hoo!" Samantha busted into her grandparent's house, Richard right behind her as they held their foam fingers, cotton candy, and the baseball Samantha caught. The inseparable pair were twinning with their Red Sox jerseys and matching hats they got at the gift shop. "Grandmary, where are you?"

"We're in the living room," Emily responded, as it was Friday night dinner.

"Guess what?" Samantha asked as she practically skipped into the living room, the red and white streaks of paint under her face making her freckles pop.

"What?" Emily questioned as Rory and Lorelai exchanged a grin, seeing how adorable Samantha looked.

"Samantha caught a foul ball," Richard made his presence known as he came in behind his granddaughter. The twin terrors struggled to hold in their laughter at the appearance of the older man that was usually dressed in a suit. They never thought they'd see the day when Richard Gilmore wore jeans.

"Papa," Samantha whacked his arm, "I was going to tell her that!"

"You did?" Emily questioned, excitedly before she held out her hand. "Let me see it."

Samantha smiled giddily as she hopped over to her and put the baseball in her hand. Emily inspected it, her eyebrows furrowing. "It's very sweaty."

"Haha," Samantha plucked it back out of her hand. "So can we eat, now?"

~:~

"I don't get why you couldn't shower before dinner," Emily complained as they sat at the table, eating their food.

"We were hungry," Samantha shrugged, Richard nodding along.

"It's true. The soft pretzels at the game were not as filling as one would think."

"I never thought I would hear dad say that," Lorelai shook her head, smiling.

"So, grandpa, how is the retired life treating you?" Rory asked her grandfather, his face immediately lighting up since he got to talk about Samantha.

"Well, quite fascinating actually. I find myself noticing things- small details- that I had never noticed before," he looked over at his granddaughter, making her eyes widen, wondering what he was about to say. "Like, for example, I've spent nearly every day with Samantha the last two weeks and I've noted several things."

"Oh, now I'm intrigued," Lorelai leaned forward.

"Like what?" Rory added.

"Well, when her grandmother comes into a room she always holds the door open for her," Richard started, making the Lorelai's awww while Emily smiled slightly. Samantha blushed, covering her face with her hand as she tried to sink down in her chair. "A lot of the time when Archibald is watching TV he can't reach the remote from his chair so he just gives up and starts crying but Samantha often will hand him the remote." He continues, making everyone laugh.

"Well, what did you expect me to do?" Samantha asked, throwing her hands up. "Just let him sit there and cry all day? Because we all know that is exactly what he would do."

"Oh another thing she does," Richard started again, causing Samantha to flop her head on the table. "Is whenever her Archie and Lucy are over, she lets them have the last piece of food."

"That is so sweet," Lorelai turned to her daughter who was refusing to look at anyone.

"I despise you all."

"Oh, and for me," Richard started again, "I can't believe I never noticed this before but whenever I come into the room, the first thing she does is give me a hug."

"Oh, I've noticed that, too," Emily pointed at him before adding, "And did anyone realize that we coincidentally have several of the books Rory talks about at dinner the next week?"

"Awww," Rory looked at her sister. "So that's how you're able to have all those long book discussions with me?"

"Shut up," Samantha responded in a sing-song voice, still hiding behind her hand.

"Okay this is the last thing," Richard said, causing Samantha to let out a silent thank god as she sat up again. "Whenever Lorelai comes over there is always a cup of coffee, and a lot of the time it's from Luke's diner," he turned to his granddaughter. "How do you even manage to get that over here? The diner is in Stars Hollow."

"It's not that difficult," Samantha shrugged. "I mean my dad literally owns the place and he taught me how to make the coffee."

"You are a literal angel, Samantha Gilmore," Lorelai shook her head as she stared at her daughter in awe. Against her best judgment, Samantha turned to look at her mother. She instantly regretted it when she saw that the older woman was looking at her how she looked at Rory. The love in her eyes made Samantha's skin crawl. Why did she keep doing that? Didn't she know that no one was supposed to look at her like that? Samantha turned to her grandmother.

"You know what? I think I will take that shower."

~:~

"It's good that you're reconciling with your mother," Lucy squeezed her friend's shoulder, "this is a good thing, Samantha."

"I know," Samantha huffed, "I still don't get why she has to look at me like that, though."

"Samantha," Archie started exasperatedly, "she's always looked at you like that. You just didn't see it and now that you do you're freaking out."

"Nuh-uh," the stubborn blond shook her head, causing both of her friends to groan. "She just started to do that now, and I don't know why. It's weird and it makes me self-conscious. That's how mothers are supposed to look at the children they kept not the ones that they abandoned."

Lucy and Archie frowned at the girl's statement, exchanging a sad glance that made the Gilmore girl roll her eyes. "Dear lord," she started. "Don't look at each other like that. I'm not upset about it I just don't know how to handle this."

"Well you could be mature and talk to her about it," Lucy suggested before Archie opened his big mouth.

"Or you could just ignore her and whenever she looks at you like that you pretend to get a phone call."

"Yes," Samantha pointed at him. "That is exactly what I'll do."

"You're idiots," Lucy threw her hands up. "Both of you."

"Hey!"

~:~

"Samantha," Emily called her granddaughter over, looking around behind her anxiously, "come over here."

"Okay..." the Gilmore girl furrowed her eyebrows as she slowly walked over and sat next to her grandmother. Her eyes widened comically as Emily grabbed her shoulders tightly, her nails digging into the girl's shirt.

"Grandmary, what--"

"I need you to get your grandfather away from me," Emily practically begged.

"Huh?"

"I just need a day where he isn't here. Everywhere I go, I can't turn around without him being there, following me, staring at me--"

"Well, he likes you."

"Stop being cute," Emily pointed her finger at her. "Now is not the time to be cute," Emily huffed. "Who am I kidding, you're always adorable."

"That's true," Samantha nodded before asking. "So what on earth happened?"

"You've done a great job of keeping him entertained so far," Emily began before pausing. "But whenver you're at your father's Richard has no one else to keep him company but me," she looked around, making sure the said person wasn't around before whispering, "he wants to join my water aerobics class."

"Ugh," Samantha cringed. "Isn't that an all ladies class?"

"That's what I said!" Emily threw her hands up. "I need you to take him or I will go insane."

"But--"

"And I'll drag you down with me!"

"Grandmary, what about my homework?"

"Richard can help you with it, just please, for the love of god, let me have a day of peace."

"Okay," Samantha held her hands up in surrender.

"Oh you have no idea how much I appreciate this," Emily pulled her grandduaghter into a suffocating hug, making her laugh before pulling away.

"Where should I take him?"

"You both are going to Stars Hollow to spend the day with Lorelai," Emily responded, making her granddaughter's eyes bulge out of her head.

"WHAT?!"

~:~

"Here we are," Richard grinned at his grandduaghter, the 12-year-old barely able to smile back as they came to a stop in front of the Lorelai's household.

"Well," Samantha opened her door, making sure her cell phone was tucked in her back pocket. "I guess we better go in then."

"Dad, Samantha," Lorelai smiled at her daughter as the pair came inside,"good morning."

"Good morning, Lorelai," Richard responded as Samantha took off his coat for him and then took his scarf.

"I'm gonna go put these up," Samantha told him, not even looking at her mother, before she walked away. Confusion spread across the older woman's face as she watched the blond hurry down the hallway. Samantha took her time putting up the outerware, taking five whole minutes to fold the scarf. When she heard her grandfather call for her, the 12-year-old huffed before going over to where he and Lorelai were sitting at the kitchen table reading the newspaper.

"Samantha," Richard held up the newspaper, "I have the comedy section for you."

"Gimme," Samantha thrust her hands out, greedily taking the paper, before hopping in his lap. She laughed at one of the jokes, showing it to Richard who also chuckled. Lorelai watched the interaction, her face crestfallen seeing that her daughter was completely ignoring her. What did she do wrong?

~:~

The minute the trio stepped into the diner, Samantha made a beeline for her father, "Lucas!"

"Samantha," Luke couldn't help but grin as he used one arm to hug his daughter since the other one was holding a coffee pot. "What are you doing here, kid?"

"Papa and I are spending the day in Stars Hollow," Samantha followed him around like a lost puppy dog as he continued to serve customers.

"Oh, that sounds fun," Luke glanced at her. "So why are you following me around?"

"I missed you," Samantha responded sincerely, causing Luke to smile again before hugging her.

"I missed you too, kiddo."

The pair was brought out of their thougts by Lorelai coming up to the counter, "I need a grapefruit."

"We don't serve grapefruit," Luke shook his head.

"Listen I have my father with me all day. There has been no major drama yet and I want to keep it that way. So you have to get me half a grapefruit for breakfast."

"I'll get it," Samantha piped up, causing both the adults to turn to her.

"You are a doll," Lorelai grinned at her, causing the girl to look up. When she saw that her mother was staring at her with that look again the girl felt her heart race in panic.

"Ding!" she pulled her phone out, causing Luke and Lorelai to exchange a bewieldered look, since they knew that Samantha made the noise.

"Oh!" Samantha put the phone to her ear. "I'm getting a call, excuse me."

Lorelai and Luke watched as the frantic 12-year-old nearly stumbled over her own feet, trying to get out of the diner. Lorelai turned to the diner owner. "Okay, what the heck just happened?"

~:~

"Alright," Samantha held up her fruit as she waltzed into Luke's diner, "I got the grapefruit!"

"They left already," Luke responded, causing the girl to sigh in relief.

"That's great. I'll keep you and Jess company then."

"What's going on with you and Lorelai?" Luke asked curiously. "I thought you two were getting closer?"

"Nothing happened," Samantha shrugged.

"You're lying."

"Yep."

"So are you gonna tell me the truth?"

"Nope," Samantha responded, popping the p.

"Oh come on--" Luke tried only to get cut off by the door slamming open by some authoritative-looking girl and a displeased-looking Rory. It seemed not one, but two Gilmore's had a plus one annoying them today.

"Samantha," Rory started as she and the inquisitive girl sat down at the countertop. Samantha furrowed her eyebrows as the dirty blond picked up a menu and searched through it as if it were holding government secrets. "You have to save mom from grandpa."

"I tried," the blond shrugged, "and they ditched me." She turned to Rory's friend, "What are you doing?"

"Observing."

"Okay," she gave the girl an odd look, before exchanging a glance with her father.

"So, Rory, who's your friend?"

"Angela Lansbury."

"Are you the owner?" Angela asked.

"Yep, you want some coffee, Angela?" Luke asked.

"No thanks, so you run the diner, huh?" she asked.

"Oh boy," Samantha puffed out.

Rory could tell this wouldn't go well. Paris was too dedicated to finding something wrong with Stars Hollow for their article and Samantha was already suspicious of her. The absolute last thing Paris needed was to say one wrong thing about Luke.

"You get a lot of truckers through here?" Angela asked.

"I beg your pardon?" Samantha furrowed her eyebrows.

"You know, guys on the road for weeks looking for a company, a little pick-me-up. Things like that."

"You do realize I'm twelve right?"

"What's she talking about?" Luke asked.

"Your guess is as good as mine."

"It's common knowledge diners are breeding grounds for prostitution and drug dealers."

"What?" Luke and Samantha questioned, in synch both of their faces scrunching up in confusion.

"Have you ever seen anything like that around here?"

Samantha leaned against the counter as the probing girl continued to fire questions at her father. She would intervene but she actually found it quite amusing. The blond snapped out of her daze when Jess came downstairs.

"Jessica!" the 12-year-old squealed before wrapping her cousin in a hug, the teenager throwing his head back in exasperation.

"Okay," he gently pushed her off, "hugging time over."

"Hey, where'd he come from?" Angela inquired. "What's up there? Is that where you keep the girls? You got a little cat house up there?"

"Uh oh," Samantha cringed. "I think she got you dad."

"Better fess up now," Jess added as he slung an arm around his cousin's shoulders.

"Do not add to this insanity," Luke attempted to scold, though it was quite difficult to take him seriously. There was a big, idiotic grin taking over his face since his daughter just called him dad again and this time she wasn't half asleep.

"An innocent boy like me should not be raised in an atmosphere like this," Jess continued, causing Samantha to snort as he turned to the girls "I wanna be good, life's just not letting me."

"Innocent my butt," Samantha shook her head, earning a small smirk from Jess and an elbow jab from Luke.

"Rory, get her out of here."

"Okay, let's go."

"Why do you need me to leave?" Angela questioned as Rory dragged her away. "What have you got to hide?"

Both Samantha and Jess waved with sarcastic smiles.

"Paris, let's go!" Rory said as she tugged the girl out of the diner, making Samantha's eyebrows crease in confusion as she looked between her father and cousin.

"Who's Paris?"

~:~

"Where are we going?" Samantha asked as Jess dragged her through town.

"You'll just have to wait and see."

Samantha followed her cousin into the video store, thanking him for holding the door open, only for her jaw to drop. "There's like four movies out here," she muttered, walking through the empty isles of children's movies and a single copy of Pulp Fiction.

"Samantha."

"Taylor," the blond turned, crossing her arms.

"Your sister has done a good deed and I will not allow you to undo it."

"Hey, don't talk to her like that," Jess defended, causing Taylor to gape at him.

"I don't know why you're in here little hoodlum but I suggest you--"

"Don't talk to him like that," Samantha snapped, making Taylor throw his hands up in exasperation before she asked, "So what good deed did my dear sister do?"

He proudly showcased the red curtain hiding half of the store. "This is the Rory curtain," he smiled sharply. "It keeps all the inappropriate movies out of the eyes of children so hopefully we may minimize the amount of you's that grow up here."

"Ah," Jess put a hand over his heart, feigning sadness, "I'm hurt." He pointed at one of the movies Taylor would definitely deem 'inappropriate.' "Why would you leave Pulp Fiction out next to the only G-rated films in the store?"

Taylor gasped, quickly gathering the movie before disappearing behind the curtain. The cousins exchanged a mischievous smirk before following him. "There, safely tucked away--"

"Taylor!" The man froze at Samantha's high-pitched voice.

"Why, I never thought you were a man who took part in such risque activities!"

"No, I was placing an inappropriate movie in its spot--"

"And you're hiding it, too?" Jess gaped. "Taylor, the first step to getting help is admitting you have a problem."

"I do not! I am not a delinquent like yourselves!"

Jess only laughed, causing Samantha's to spill over. They stopped abruptly when Taylor picked up the landline. "Time to bail!"

Samantha quickly grabbed Jess's hand, yanking him with her as she swung the door open. They looked back, not being able to hide their grins when they saw that Taylor had attempted to chase them. He gave up after five feet and then proceeded to shout at them from afar. The 12-year-old let out a string of giggles as they turned the corner, passing Rory and Paris--one of which seemed a lot glummer than her blond companion.

"Hey, wait! I need to interview you for this article!"

"Sorry, no paparazzi!" Jess shouted, waving a hand in the air. "Ms. Gilmore is busy at the moment!"

The pair kept running, burning the soles of their shoes from the friction against concrete until they reached a secluded patch of grass and collapsed. "I cannot believe the only tolerable person in Stars Hollow is related to the Rory-Curtain."

"Yeah well," Samantha sighed as she laid her hands on her stomach.

"Oh come on," Jess turned to her. "Don't let Taylor get in your head."

"Maybe he's right," Samantha shook her head. "Rory's the golden child who everyone loves and I'm the error that should be in Hartford, not being a burden to everyone here."

"If anyone's a burden," Jess started as he lifted his finger to himself, "It's me, not you." He paused before adding, "And I think it's crap that you get treated like less just because you're not the same person as your sister."

"We can be burdens together," Samantha smiled at him, making Jess smirk slightly as he wrapped an arm around her.

"Yeah, burdens together."

~:~

Samantha was later than the rest of the Gilmores. By the time she got to the Lorelai's house, Lorelai one was writing a neat list, and Richard and Lorelai two were chatting in the kitchen behind her.

"Okay," the youngest Gilmore made her presence known as she stomped over to her grandfather. "I have a bone to pick with you."

"Uh oh," he looked between the twin terrors. "I think I'm in trouble."

"I have been carrying around this grapefruit all day," Samantha held up the fruit that has served as a nuisance for the past seven hours, "and I have juice all over my clothes!"

"Oh dear," Richard chuckled heartily. "That is a predicament."

"It's not funny, Papa!"

Samantha cut herself off when Richard had to bend down because he was laughing so hard. The 12-year-old exchanged a glance with Rory, the latter not being able to hide her grin, before they both burst into laughter, Lorelai soon joining in. A honk snapped the group from their moment. Richard and Dean had taken the car the teenage boy built for Rory to Gypsy's. Apparently, Richard didn't think it was safe for his oldest granddaughter to drive and insisted on taking it to a professional. This left Samantha in the worst position possible.

"Sam," Lorelai grabbed her arm and dragged her to the living room, "come talk to me for a second."

"I think I'm getting a phone call--"

"Your phone is off."

"Rats," the blond huffed as she and Lorelai sat on the sofa.

"What's going on with you lately?" the older woman nudged her shoulder. "I thought we were making progress, but then you shut down on me again," she paused, seeing that her daughter still wouldn't look at her, before joking, "I'm getting whiplash from all of your mood swings."

"Nothings going on," Samantha mumbled, "everything's fine."

"Come on," Lorelai proceeded to grab both the girl's shoulders and shake her back and forth, "tell meeee."

"Lorelai," Samantha laughed, finally looking up at the woman. When she saw that her mother was giving her that look again she immediately sprang up from the couch, slightly startling the woman. "I'm gonna go find an uber."

"Samantha," Lorelai hurried after her, onto the front porch, and grabbed her arm. "What did I do? I need you to talk to me."

"You didn't do anything! Everything's fine!"

"Are you upset that I didn't take your money for the loan?" Lorelai asked, thinking about when all of this started, making her daughter give her an incredulous look.

"No, of course not."

"Then what did I do?!"

"Y-you, you," Samantha stuttered as she paced around before finally facing her mother. When she saw the warmth, worry, and despair in Lorelai's eyes, the look that only a mother could give, she finally exploded. "You aren't supposed to look at me like that!"

"Look at you like what?" Lorelai asked, bewildered.

"Like how you look at Rory!"

"What?" Lorelai asked, her voice barely above a whisper, as her daughter continued to pace in front of her.

"You are not supposed to look at me like that," Samantha shook her head furiously. "In fact, no one is supposed to look at me like that. That's how you're supposed to look at Rory."

"Look at her like what?"

"With love in your eyes," Samantha threw her hands up as tears sprang to her eyes. "The fact that you're looking at me like that is terrifying. That's how you look at the kid you kept not the one that you left. Don't you know that?!"

"Well I do love you--" Lorelai felt her heart breaking as she tried to convince her daughter that she did, in fact, love her.

"No!"

"No?"

"You can't change your mind now," Samantha turned to her, "you're freaking me out!"

"Well, you're freaking me out!" Lorelai shot back.

"I just need you to not look at me like that and then everything can go back to normal, okay?" Samantha tried to reason with her.

"Well I can't do that," Lorelai shook her head. "Because that's how I feel. I regret leaving you more than anything. But it doesn't change the fact that you're my kid and I love you!"

"No," Samantha had to bend down, suddenly having trouble staying upright as her chest heaved up and down. Lorelai immediately ran over to her.

"Deep breaths honey," she rubbed her back as she brought her into a hug. "Deep breaths."

"I still don't want you to look at me like that," Samantha grumbled as she wrapped her arms around her mother, making the woman grin.

"You'll live."

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