I know the last thing I should be doing is starting a new chapter story, but I couldn't resist. I was originally writing this for Kiss Me Fool, but the idea got bigger than a little drabble. This is a literati friendship fic. I haven't decided if I'll get them together by the end. This story is set during Presenting Lorelai Gilmore, which means it covers Rory's Debutante Ball. Dean doesn't exist. Rory asks Jess to escort her to the ball since he has been her friend for years.

Disclaimer: I claim to own nothing. Everything recognizable belongs to rich and important people. Some conversation is taken directly from Presenting Lorelai Gilmore.

"Rory! How could you let Emily Gilmore con you into doing something like this?" Lorelai exclaimed.

"Mom! Grandma only wants to be included in our lives. Stop being so mean to her!" Rory looked around for one of the diner boys to take their order. The sooner there was food, the sooner the conversation ended.

"But there's so much stupid planning for this stupid ball!" Lorelai whined.

Rory sighed. "Suck it up. I already told you I wanted to do this for grandma."

"Why?" Lorelai asked. "I've never wanted to attend another one of these silly events. We need to find you an escort; I need to call your father; we need to get you a dress. There's so much to do!"

"Wait. Back up to the part about dad. Why do you have to call dad?" Rory asked.

"Your father is supposed to present you at the ball."

"You never told me that! He's never going to come. Dad's worse than you when it comes to these events." Rory looked down at the table sadly. It wasn't even busy. Luke or Jess should have been over to take their orders by now.

"Sweets…"

"Whatever, it's no big deal. I can get someone else to do it. Grandpa probably, or Taylor." Rory looked around for either Luke or Jess to end the conversation.

"Rory..."

"The cable guy looked pretty friendly last week. Maybe he has a tux," Rory cut Lorelai off and continued to ramble.

Lorelai dug her phone out of her purse.

"I was kidding about the cable guy. What are you doing?" Rory asked frantically. This would have been the perfect time for Jess to show up with his order pad in hand.

"Look missy, there are plenty of things that should weird you out about coming out, but inviting your father shouldn't be one of them." Lorelai searched for Christopher's name in her cell phone contact list.

"He's not going to come." Rory knew her father's track record. He was not very good at showing up to events that mattered to her. He had missed some her of proudest moments, including many of her birthdays.

"You don't know until you ask." Lorelai found the right number and pressed the send button.

"Mom…" Rory pleaded. She was still looking around for Luke and Jess, specifically Jess. He knew how to lighten any moment. They must have been alone somewhere arguing, as they tended to do occasionally.

"Look, we call, we ask, there's no harm. Trust me; cable guy's not going anywhere." Rory scowled at the proposition.

Jess eyed Rory as he stepped downstairs with Luke. She had been right. Luke probably had a bone to pick with his nephew. He headed over immediately with two coffee mugs and a coffee pot. "My hero," she gushed as Jess filled her cup to the rim. "Where have you been?"

"I took a twenty out of the register and forgot to tell Luke. Apparently, that didn't sit well with him. I told him I'd give him the money back, but he still had to yell at me first." Jess pulled up a chair. "What's going on with this?" he asked, motioning to Lorelai chatting with Chris on the phone.

"Oh, nothing," Rory said as she sipped her coffee. "Just a catching up phone call between my parents."

"Oh. Awkward." Jess set the pot of the table as Lorelai thrust her mug at him. He filled it and stood up. "Do you want to order now?"

"Yes!" Rory exclaimed.

"Wow, aren't we jumpy tonight," Jess said.

Lorelai ended the call and stuck her phone back in her purse. "Hey, Little Debbie, your dad is definitely going to be there."

"You're kidding!" Rory exclaimed. Jess started to leave, but she pulled on his shirt for him to stay.

"No. He's going to walk you down the stairs, and turn you in a circle, watch you curtsy, and announce that Rory Gilmore is officially open for business!" Lorelai drank her coffee slowly and waited for Rory to respond.

"I can't believe it. And he definitely said definitely?"

"Definitely."

"So there's a fifty/fifty chance," Rory said hopefully. She looked up at Jess. He was confused, but still listening.

"I don't know. He sounded pretty sure. I'd say sixty/forty."

Jess held up the order pad. "I've only been standing here for ten minutes. Should I wait longer?"

Jess scooped vanilla ice cream into two cones. Rory gratefully grabbed her towering ice cream and licked it.

"Jess?" Rory asked timidly.

Her best friend groaned. "What, Rory?" As he waited for her to answer him, he stuck the ice cream in the back of the freezer.

"I know it isn't your scene…"

"Then no." Jess joined Rory at the counter in Luke's. It was well past ten at night on a Saturday. The diner had closed, so Jess invited Rory over for ice cream cones. He hadn't realized she would try to rope him into doing her a favor at the same time.

"Come on Jess! Don't just say no," Rory begged. She batted her eyelashes at him, which caused him to roll his eyes.

"What is it this time?" he asked as he caught a drip sliding down his cone.

"There's this event Grandma was telling me about. It's called the Debutante Ball."

Jess raised his eyebrows at the word ball, and knew she was trying to get him to attend a fancy shmancy rich people's dance.

"It's my coming out," she stated bluntly.

His reaction was a domino effect. Jess laughed, then snorted, then dropped his ice cream cone on the floor. "Coming out of what? Out of the closet?" he asked as he frowned at the ice cream melting on the tiles.

"JESS! NO!" Rory shouted. She pushed him lightly and he fell off the stool and into the melting ice cream.

"All bets are off now. I have ice cream on my pants." Rory helped Jess to his feet so she could explain what the Debutante Ball was.

"It's a ceremony where I come out as a lady," she said.

Jess scoffed. "I bet Lorelai was all over the idea."

"Well, you know how mom is about these events. She tried her hardest to avoid them when she was my age, and then fled from that lifestyle to protect me. She tried to talk me out of it."

"Of course she tried to talk you out of it," Jess said. He hopped off the stool to start cleaning up the ice cream before it got sticky. "She hates the idea of spending time with the rich people."

Rory scrunched up her nose. "I though about that, but grandma was so upset when mom didn't attend her Debutante Ball. Mom first realized she was pregnant because she couldn't zip her dress. I guess I want to give that to grandma."

"Ah, aren't you nice?" Jess cooed mockingly. "I'm going to get some cleaner and another ice cream cone." He eyed Rory sucking the ice cream out of her cone. "Do you want a refill while I'm in the kitchen?"

"Do you even have to ask?" Rory joked as she handed Jess her empty cone. "Pack it extra tight; you can fit more in the cone if it's packed tighter." She smiled with glee. "Hurry back!" she added.

Jess vaguely recalled when the mother and daughter pair were chatting earlier that afternoon. This event must have been important if Christopher was supposed to be included. Jess had witnessed the aftermath of Chris not showing up to Rory's special events, such as her elementary school graduation, her seventh, eighth, ninth, twelfth, thirteenth, fourteenth, and fifteenth birthday parties. He scooped the ice cream into the two cones. If Chris didn't show up, it would break Rory's heart again. It pained him to do so but, if Rory needed him to, he'd attend her ball.

Rory was patiently reading The Fountainhead while she waited for Jess and her ice cream. Jess handed Rory her cone and started to mop up the floor. They were silent until he rolled the mop bucket away and immerged with his own cone.

"Tell me more about this Debutante Ball," he requested.

"It's silly," she said, brushing him off. "You wouldn't want to go."

"It depends," he said, "on what I have to do."

"You'd have to be my escort. You'd have to dress up in a fancy tux and cummerbunds and gloves." She sighed. "My dad is supposed to be my other escort. I don't know if he's going to come or not. It would mean a lot to me if my best friend could be my secure escort."

Jess licked his ice cream. "Okay. I'll do it," he said.

"What?" she asked, surprised that Jess was going to escort her.

"I'll do it," he repeated.

Rory shrieked and lunged at Jess to hug him, knocking both the ice cream and Jess on the floor.

He looked up at her from the floor. "You owe me a pair of pants."