A/N: To make up for not actually writing about their date in the last chapter, I present to you a Very Special double chapter, with twice as many words and approximately five times as much Jess. I hope you like it!
Rory started to feel nauseous around six on Saturday night. Paris tried to get her to breathe into a paper bag or take a Xanax, but Rory settled for pouring a massive cup of coffee and picking at her nail polish. She had never been the best at waiting for things, and waiting for her date proved to be incredibly nerve-wracking. As each minute passed, she was a little more convinced that Jess wasn't going to show up. There was absolutely no logic or reason behind that thought, but she feared it nonetheless.
At 6:52, someone knocked on the door. Rory's heart immediately jumped into her throat. She had been looking out the window regularly to see if she could spot Jess, but he must have snuck by when she wasn't paying attention. "Paris, answer the door," Rory hissed.
Paris shook her head, but got off the couch and headed to the door. "You're pathetic," she said. Rory couldn't argue with that. She tried to calm down as Paris opened the door. "Hi, Jess."
"Hey," Jess said. Rory considered escaping to her bedroom and hiding, but Jess could see her from the door and would probably notice if she didn't come out of her bedroom.
"I was just putting my shoes on," Rory said, hoping that would explain why she had sent her roommate to the door instead of answering it herself. Never mind the fact that she had put her shoes on almost an hour ago. "I'm ready to go now, though."
"Great," Jess said, looking at her a little quizzically. For a moment Rory almost panicked again. Had he shown up to cancel or talk about the paper instead of go out to dinner? "You might want to grab a jacket though," he continued. "It's pretty cold out."
Rory looked down at the tank top she was wearing. She had spent half an hour trying to pick out a sweater to wear and then in the process of getting dressed she had forgotten to actually put it on. "Right. I'll be right back." As fast as she could, she ducked into her room and pulled the sweater on, cursing herself for looking like such a dork. She put her shoes on an hour early but couldn't even get dressed properly.
"Ready for real?" Jess asked when she came out of her room. She nodded, pleased to see that he was dressed casually. He was in jeans and sneakers like her and was wearing a gray zip up sweatshirt. Rory thought he looked pretty great. Hopefully he thought the same thing about her.
As they walked to the restaurant they talked a little bit about the paper, but Rory tried to steer the conversation away from actual work. Even though they were both on the paper and he was her editor, she didn't want to spend the whole evening talking about the state of the article she was working on. "So has Doyle always been so…?"
"Wound up?" Jess suggested. Rory nodded. "Since day one at the paper. We were both assigned to the news beat and he had enough energy for the entire staff. He was the first one at the scene of anything newsworthy, even if he wasn't covering it. I'm not surprised he's editor now. If he doesn't end up at the New York Times or somewhere I think his head will actually explode."
Rory laughed. She could definitely see that happening. "So what drew you to the paper? Are you secretly vying for Doyle's future spot at the Times?"
Jess shrugged. "I don't think so," he said as they walked up to Rich Man's Shoe. "I like the paper and everything but I don't think journalism is for me, you know? I just joined the Daily News because my dad wanted me to."
Being on staff, especially as an editor, was a big commitment for someone who wasn't really into journalism. Rory definitely made a note to bring it up again during dinner. For a few minutes they were occupied with finding a table and getting their menus. Once their waitress delivered their drinks, Jess switched topics. "So, you have big Halloween plans next week?"
"Oh, sure," Rory said. "Trick-or-treating is my favorite."
"My buddy Finn is having a party," Jess said with a laugh. "I talked him into making it American Horror Story themed. Now I'm pretty sure that means half the girls will show up as the young version of the maid from Murder House, but it should be fun. I think he's bought out every liquor store in the greater New Haven area." He looked at her expectantly.
"Sounds fun," Rory said, taking a sip of her Coke. "Very appropriate theme."
Jess looked amused. "I was thinking you could come with me."
Rory probably should've put that together sooner, but she was still surprised. "You want me to go to a party with you?"
"If you want," Jess said. "It's a costume thing, but you could probably just wear anything and say you're Violet or someone. Have you seen American Horror Story?"
"Yes," Rory said. "Has Finn, though? There isn't a lot going on in the way of costumes, unless you want to be a maid or a nun or something."
"I don't think he has, actually," Jess said. "He'll forget about the costume thing after a couple of drinks, though."
"I'm not a big drinker," Rory said uncertainly. That was a big understatement. The closest she'd ever come to having a drink was taking a sip of Miss Patty's punch once. Her mom had been trying to warn her against drinking, and it had worked. It was like sipping on poison.
Jess didn't look concerned. "You don't have to drink," he said. "I'm sure there will be at least a couple of people there not drinking. Or not drinking much. Someone has to drive home."
"Right," Rory said, though she still wasn't sure why Jess even wanted her to come with him. She wouldn't know anyone at the party besides him, and she had a feeling there wouldn't be a lot of other freshmen at the party. She didn't want to stick out.
"Hey, just an idea," Jess said, sensing her hesitation. "I know it sounds like a big thing, but it'll be pretty relaxed. My friends are cool. They'll like you."
Meeting Jess' friends sounded a little scary. If Jess was from a "fine family" like her grandma said, that meant he was probably friends with people in similar situations. Rory had nothing against wealthy people or legacy students, but she always felt like they could tell she didn't quite belong with them. She was like Bargain Mart to their Bloomingdale's. In the back of her mind, though, she could almost hear her mom chastising her. College was about making friends and meeting new people. She was going to turn down a party with a cute guy just because she was worried she wouldn't fit in? How would she ever know if she didn't try?
The waitress came back to take their order before Rory could answer, but she felt a lot more calm after she ordered her bacon double burger and fries. "The party sounds fun," Rory said. "I'd love to go."
"Cool," Jess said with a smile, fiddling with a sugar packet. "Hey, I bet I can push this through the table."
"You can?"
"Sure," Jess said, setting a salt shaker on top of it. "You need something flat to push it through," he explained. He laid his napkin over top of the salt shaker and hit the top of it, but when he moved the salt shaker the sugar packet was still on the table. "Huh. Hand me another packet, one of the blue ones."
"You think Equal will be easier to push through solid wood than real sugar?" Rory asked, handing him the packet.
"Maybe," Jess said, setting the shaker back on top. When he pushed down on it the napkin flattened on the table. When he picked it up, the sugar was still there but the salt shaker was gone. "Huh. I think I did it wrong."
"Now I'm going to have to put sugar on my fries," Rory said. "You know, when you cover up what you're doing with a napkin it looks very suspicious."
"But you were focusing on the sugar packet, right? You didn't even notice when I dropped the salt shaker."
Rory had to admit he was right. It was a pretty cool trick. "I didn't picture you being into magic tricks," she said. Learning magic tricks seemed so supremely dorky that she couldn't even imagine him sitting down to try.
Jess shrugged. "You've got to keep people on their toes," he said. "My dad told me that people should never feel totally comfortable around you."
"That's some advice," Rory said, thinking about her mom. She felt more comfortable around Lorelai than she did around anyone else in the world. "Are magic tricks his way of accomplishing that?"
"No, he's just really passive aggressive and manipulative." Jess said it casually, but Rory felt kind of bad for him. She didn't know anything about his dad, but passive aggressive and manipulative weren't exactly compliments. "He owns a lot of businesses. Newspapers," Jess added by way of explanation. "He's used to dealing with staff, not his kids."
Rory had no idea what to say to that. "My mom's working on opening an inn," she said. "Businesses are definitely stressful. So, is that why you're on the paper? So you can have your own papers someday too?"
"That's the idea," Jess said. "I haven't really figured out a way to tell my dad I don't actually want to do that, but I figure I've got some time to figure that out before he sticks me in a suit in a boardroom."
So now Rory knew something about Jess besides his name. He liked magic tricks, not journalism. "What do you want to do instead?"
"I don't know. Something, probably."
"A great alternative to nothing," Rory said. "I'd rather write for a paper than run one."
"I like writing fine, but I don't really like the journalism format. It's too structured. There are too many rules."
Rory could understand that. It was a little jarring to switch from writing essays and things to writing news stories, where the information was usually in an entirely different order. She had never been one for writing fiction or anything, but she'd had plenty of papers to write at Chilton that were a lot different than her articles for the Franklin. "That makes sense," she said, though her attention was momentarily stolen by the incredible looking burger their waitress set down in front of her. "Wow, this looks amazing."
"I told you they have good burgers," Jess said, adding salt and pepper to his fries. Rory hadn't even noticed him put the shaker back on the table. "You want the ketchup?"
"Yes, please," Rory said. As she added some to her fries, she took a moment to reflect on the date. So far, so good. The food was great, and there hadn't been any weird lulls in their conversation. She didn't know much about his family and she wasn't even sure where he was from, but skipping the small talk in favor of actual conversation was always a plus in her book. Not to mention the fact that he'd already asked her out again and the date wasn't even over yet. She desperately wanted to know why he would do that since he didn't even really know her, but she was hardly going to ask him. It didn't make much sense, but she wasn't going to push her luck. If Jess liked her then that was 100% okay with her.
