Takes place 20 years after the finale. Rory and Jess got back together and ended up having a little girl, Lily Hayden Gilmore-Mariano. This is the story of her first date. I own nothing except Lily and Sam. Don't forget to review.
Being a dad came easier than expected to Jess. His daughter was pretty easy going, like her mom. She never got in trouble, did her homework, made good grades. Again, just like her mother. She was his little girl. Okay, so maybe Rory Gilmore was not a Daddy's Girl by any means, but that was the one exception Jess was okay with.
Rory walked through the door holding two bags full of food. "I brought the dinner!"
"Thanks babe," he kissed her and saw the bags. "Luke's." He laughed. "Ya know, maybe we could go somewhere outside my uncle's."
"Now what fun would that be?" She started set the food onto the table and started digging through the cabinets.
"What are you looking for?"
"Candles."
"Candles?"
"Candles."
"Since when does dinner at the Gilmore-Mariano residence equal candles?"
"Since we're going to be all alone for dinner," she smiled. "I would say we could go out, but I'm just too exhausted. There was so much traffic."
"Why are we going to be alone for dinner? Is Lily sleeping over your mom's?"
Rory bit her lip. "Uh, well no. She's not sleeping over my mom's."
"Study group?"
"No."
"Off painting the town? Rory, cut to it. Where is Lily off to?"
Rory set the candles down and took her husband's hands. She gave him a beautiful smile and kissed his cheek. "I love you."
"Rory."
"Okay, well...you see…Lily has a date."
Jess' eyes about bulged out of his head.
"No. She's too young!"
"She's fifteen. I was fifteen when I started dating my first boyfriend."
"I thought it was technically on your sixteenth birthday."
"Only because I was scared. Jess, she's so excited, okay? She couldn't stop talking about it," Rory explained.
"Well good, now she has something to look forward to, when she's forty!"
"She's not a baby anymore. In a few years she'll be off at college…"
He groaned. "Don't remind me."
"She's a smart girl. She can handle herself."
"She's not going." He kissed his wife. "Now I'm gonna go upstairs and tell her that I'm locking her in her room until she's forty."
Jess walked upstairs, his mind spinning. It seems like just yesterday that his little girl was getting off her knees and walking. Not long after that, she was starting at school. She clung to her daddy's leg and refused to let go. Jess had to stay for the first hour. As she grew older, they had more complex conversations, about literature and music. She was a great girl, a sweet girl. He wasn't about to let his little girl get heartbroken.
He took a deep breath and knocked on the door. He heard a faint "Come in!" just a second later, so he followed the command. Sitting at her vanity, was his little girl. At all of fifteen, she was a spitting image of her mother. Straight brown hair, very pale skin. The one thing she did have, light brown eyes. She was out of her Chilton uniform and in a pink dress, one Lorelai had brought by. It wasn't too short, but not too long either.
"What's up, Daddy?" Lily asked as she grabbed some makeup. Jess winced. If he had told her once, he had told her a million times. She was beautiful without makeup.
"Your mom told me you have a date."
"Yes! He's going to be here in thirty minutes."
He sighed and sat down on her bed, picking up her teddy bear.
"Lily…"
"He's not a guy from Chilton, he goes to school with Martha," she explained. "I met him at her birthday party."
"That sounds nice but…"
"We're going to the movies and then Al's. I was going to suggest Uncle Luke's, but I figured it'd be nice to switch it up."
Jess went to speak again and then saw the look on his little girl's face. She was so happy, she was grinning from ear to ear. She was genuinely excited about this date. If he told her he couldn't go, that smile would be gone and it would be his fault.
"Don't go to Al's, you'll get sick," he advised. "Go to Jo Jo's."
She smiled. "That's a brilliant idea, thanks Daddy!" She hopped up and kissed his cheek then giggled.
"What?" She pointed to his cheek and he touched it, only to find lip gloss on his hand. "Lily!"
"Sorry, can't help it!" She reapplied the lip gloss.
"So…that lip gloss won't be going on anyone else tonight, right?"
She rolled her eyes. "Dad."
"Just know that you don't have to do anything you don't want to."
"Daddy! Not this talk! Mom already gave it to me."
He raised his eyebrow. "She did? When?"
"When I got my period."
"Okay, okay, Dad out." He kissed her head and walked out, shutting the door behind him.
"So, no tears, no screaming?" Jess whipped around to see Rory standing there with her arms folded. "She must not really like him."
He rolled his eyes and started walking downstairs. "I didn't tell her she couldn't go."
"Ha! I knew it, you can never say no to her."
"I say no all the time."
"You do not."
"I do so."
The doorbell rang and Lilly came running down the stairs past him. She checked her reflection in the hall mirror before going to the door and swinging it open. That's when Jess' eyes bugged out of his head for the second time that night.
There stood a tall sixteen year old boy dressed in black leather and Metallica t-shirt.
She had heard the psycho babble before. Girls go after a spitting image of their father. But this was too much. He walked down with Rory.
"Hey Sam," Lily said with a big smile.
""Sup?"
No. No way. He turned back to Rory and with a harsh whisper, Jess told her. "Okay, I'll have no problem saying no, now."
"Jess!" Rory whispered back.
"She is not going out with that punk! He…he…he looks just like me in high school!"
She smiled and patted his shoulder before going downstairs. "Sam, Lily, you two have fun. Be back by ten thirty, okay, love?"
"'Kay. Bye Mom, bye Daddy." She grabbed her purse and walked out with Sam, shutting the door behind her.
Rory was starting to get annoyed. At first it was cute about how worried Jess was, but they rarely had dinner alone. Now here they were, with their one chance and he was freaking out.
"She's fine, Jess."
"What if that punk hurts her?"
"Jess."
"What?"
"Did you hurt me?"
"Yes, I threw Shane in your face, I left without saying goodbye, I blew off your graduation…"
"Okay, but all of that was circumstantial. Sam is not going to do that."
"How do you know?"
"Because I have faith." She poured herself more wine.
"Lily is such a happy kid. If he makes her cry…"
"He won't."
"But if he does."
"Then she'll have us."
He bit his lip and took a bite of his burger. "What if she doesn't need me anymore?"
"Oh Jess!" She sighed. "I felt the same way. She's growing up."
"See!"
"But guess what, she's always going to need us. Hell, I still need my mom."
He sighed and nibbled on a fry.
"Now," she whispered. "I have an idea. Why don't we push Lily out of our heads for now and enjoy some adult conversation."
He thought about it for a minute but finally relented. "Alright. I will enjoy this time with my beautiful wife."
She grinned and kissed him.
Jess sat in the living room, reading a book. The clock was ticking loudly in the background. He looked up and saw the time. 10:25. Just at that moment, he heard a car pull up in the driveway. He put the book down and went to the window. He could see the beat up Impala, but he couldn't see past that. A moment, which felt like an hour, later, Lily stepped out of the car, a smile on her face.
"Okay punk," he whispered. "Walk her in, walk her in." But instead, the car zoomed off. He bit his lip, anger growing inside of him. That was it. The moment Lily walked in. He quickly moved away, grabbing his book. "Hey Pumpkin."
"Hi Daddy," she said, with a smile, completely oblivious to her spying dad.
"How was it?"
"So much fun!" She kicked off her heels and let her straight hair out of a bun. "Daddy he's perfect."
"He didn't walk you to the door."
She rolled her eyes. "That's old fashioned."
"Lil…"
"He paid for everything, even though I told him not to. And he held my hand!" She squealed. "Where's Mom?"
"Upstairs getting ready for bed."
"I need to go tell her everything!" She kissed his cheek and ran upstairs.
Jess walked into his room an hour later. Rory was curled up in bed, with Lily by her side, her head on her stomach. She was no longer in her dress, but instead flannel pajamas, still pink of course. He couldn't help but smile.
"What is she doing in here?"
"She was filling me in on every detail of her date."
Jess settled on the edge of the bed, looking at his little girl. "And?"
"Completely innocent. It ended with a kiss on the cheek."
He let out a sigh of relief. "Good."
"One day Jess, it will be more."
"I don't want that day," he whispered.
"I know but it will. But if we keep up this trust, she'll tell us." Jess nodded. "I'll wake her up, she can go back to her room."
"Nah, she can spend the night in here with us. Like she used to. She doesn't have to grow up all at once does she?"
Rory grinned. "Definitely not." They each kissed their little girl on the head.