A/N: This chapter's going to be a two-parter since it was getting long! Unfortunately I haven't actually written the second half of the chapter yet but hopefully I can get that done soon!

Rory's could hear her own heartbeat in her ears as she hung up the phone. She had never asked a guy out so directly before. She hadn't really asked a guy out before at all. In college a boy in one of her classes had asked her out and she turned him down only to turn around and talk around the subject until they set up a date, but that wasn't the same thing as actually asking him out. There was a first time for everything, though. Even if nothing else changed going into the new year, she could at least say that she tried something different.

And even though she was filled with adrenaline over actually asking Jess on a date, she was somewhat happy knowing that this was likely a one-time thing. Knowing that Jess would be going home fairly soon and that the date couldn't really turn into anything was comforting. It wasn't like with Dean, who was always clingy and eager to please, or Logan, who was a whirlwind of excitement—and drama. Both relationships had spanned years, and both had been incredibly taxing at times. This would truly just be a date. Yes, Jess had seemed like he could perhaps be a little intense before, but a couple of drinks and some free entertainment seemed like a good way to relax.

For a couple of hours, Rory was relaxed. Just knowing that she was going to get out of the house to do something fun gave her the energy to straighten up her room. She had fun for a little while going through some of the clothes she had left behind at home (a below the knee jean skirt was quickly tossed into the "donate" pile). Nothing that had been left behind was particularly appropriate for a date, but for once she wasn't too worried about dressing up. Is this what she had missed out on in college by being in relationships? She had known people who seemed to have a different date every weekend and it had always seemed stressful to her, but now it seemed like casual, no-strings-attached dates could actually be fun.

The only glitch with the date was that Rory didn't actually want her family to know she was going out with Jess. Her mom had been pestering her months about why she wasn't dating, and Jess was related to April and Luke, which made the whole thing a little bit strange. When she saw a car pulling into the driveway she dashed to the door, eager to slip out without too much questioning. "I'm going out and I've got a ride!" she called into the living room as she opened the door. "Don't worry about waiting up!" She wasn't sure how late she would be out, but she was 23 years old. It wasn't like she had a curfew.

"Did you sneak out or something?" Jess asked when Rory climbed in the car. Judging by the car seat in the back he had borrowed the car from his mom. Too late, Rory realized that her own car was sitting in the driveway where she had left it seven months earlier. She was so used to not having it she didn't even think about picking Jess up. Of course, he knew where she lived already.

"No, I just didn't want to deal with a million questions about who I was with and where I was going," Rory said. "My mom is cool, but she's been not-too-subtly asking about my dating life for months now. I never would've made it out of the house if I actually told her I was going on a date." She let the last part hang there, wondering if Jess would say anything about their date.

He let it pass. "Luke might have thought it was kind of weird," Jess said. "He seems kind of awkward with people."

"A little," Rory said. "But he's really great. I've known him since I was a kid."

"I could probably count the number of times I've seen him on one hand. My mom had a habit of kind of going off into her own world. She was always caught up in one boyfriend or another. Believe it or not, TJ has been the best of the bunch."

"I liked TJ!" Rory said. "He was funny. And he was so sweet with your sister. Turn left up here," she added. "Believe it or not, KC's is actually in Stars Hollow. Taylor, the guy who owns the grocery store, tried to take their liquor license away a couple of years ago after this guy Kirk got drunk and tried to jump onto a moving golf cart and skinned his knees. When that was shot down he wanted to rezone so that the bar technically wasn't in Stars Hollow, but that didn't work out either."

"What, he didn't appreciate karaoke night?" Jess asked, pulling into the parking lot. There were only half a dozen other cars there. Karaoke night wasn't intensely popular. Then again, it was still pretty early.

"I don't think he's even been to karaoke night. I can't imagine what he would say about Babette and Miss Patty signing up for ten slots in a row. He'd probably have them arrested for not taking turns or something." Inside, Babette and Miss Patty were already at the bar, warming up for their act. Rory wondered which would be worse: Babette and Miss Patty telling everyone Rory had gone out on a date with Luke's nephew, or them telling everyone that Rory had gone out on a date with a mysterious stranger that no one in town knew. Figuring it would get out one way or another, Rory ordered a couple of beers while Jess grabbed a table. Luckily, Babette and Miss Patty were too busy going over their set list to pay her any attention.

Joining Jess back at the table, Rory took a minute to look around. It looked exactly the same as it always did. "My mom sang karaoke the last time we were here," Rory said. "Actually, it was the only time I was here with her. It was right before I graduated and she sang me a song to cheer me up."

"How'd she do?"

"Not too badly. Of course, she sang "I Will Always Love You" so the whole town was talking about her and Luke maybe getting back together, but it was nice in the moment." It felt like a lifetime ago already. Rory had more or less forgotten about the Reston Fellowship since she got the campaign job. It was funny how something she had stressed (or obsessed) about for months completely faded away when something else came along. "No matter what my mom said about the song I think everyone else was right, because she and Luke got back together a couple of weeks later. You probably didn't come here to hear about my mom's love life, though."

"Hey, it's sort of related to me," Jess pointed out. "I'm learning more about Luke. I still don't really know anything about you, though. For instance, you graduated. Where'd you graduate from?"

"I went to Yale," Rory said, quickly taking a sip of beer. She was proud of her academic accomplishments, but after hearing so many people on the road boasting about whatever college the graduated from she was worried about sounding like she was bragging.

Jess just nodded. "I've heard that's a pretty good school."

"I liked it," Rory said. "There were some really amazing teachers there."

"See, you said 'amazing teachers', but I heard 'amazing parties'."

Rory shook her head, laughing. "I wasn't really the partying type. My roommate tried to throw a party in our room freshman year, but it didn't really work out. And then she held a wake for her boyfriend in our dorm the next year, but that was a little different."

"A wake?"

"Her boyfriend died. He had a heart attack."

"You don't usually hear about college kids having heart attacks."

"He was slightly older. He and my grandpa were friends in college. She was a bit… eccentric." That was always a safe word to describe Paris.

"Obviously," Jess said. "What about you? Did you date any of your grandpa's friends?"

"I thought you weren't supposed to talk about your exes on first dates," Rory joked. Like she would even know. "No, I didn't date any of my grandpa's friends. I did date a guy for a few years in college but it didn't work out." Technically that was true on two counts, but she had dated Dean so briefly in college that it hardly counted as a grand college romance.

"At least he didn't die of a heart attack," Jess said. "Unless he did?"

"No, he moved to California. He did want me to come with him and marry him, but I told him it was too soon so he broke up with me." It didn't hurt as much to say as it had in the past, but it still wasn't a particularly fun. "What about you, though? I don't know anything about you."

"I actually was engaged for a while last year," Jess said. Rory nearly choked on her beer. She hadn't expected that. "But then she joined Greenpeace and moved to Amsterdam or somewhere. I haven't heard from her since. She said she couldn't be 'tied down' anymore and that there was more to life than living in Philadelphia. I think she was probably actually seeing someone else, because she had never particularly seemed interested in the environment before."

"Yikes," Rory said, draining her drink. "You want another one? The karaoke is going to start soon and believe me, you might need another drink to sit through all of Patty and Babette's songs."

"I'll get them," Jess said, walking up to the bar. While he was ordering the drinks Rory sneaked a look at her phone. Unsurprisingly, her mom had texted her. Busy, will talk later, she texted back. Too late, she realized Lorelai would probably think she was out doing something salacious instead of just having a drink with a new friend. Of course, Jess hadn't corrected her earlier when she said it was a date.

Babette and Patty were taking the stage when Jess came back to the table. "So now the magic begins?" he asked, handing her a drink. "I have to admit I was skeptical about going to a karaoke bar, so it better be as good as you said."

"Oh, it'll be great. While you were up at the bar I signed you up for a couple of songs, so just be prepared for that."

"You did not." Jess narrowed his eyes at Rory. She shrugged. "You are joking, aren't you?"

"Karaoke works a little bit differently in Stars Hollow. Here, you just sign up your friend while they aren't looking and then they have to go up and sing whatever song pops up on the screen. It adds an extra level to the whole thing. There aren't any scores or anything so no one technically wins, but this way people definitely lose. We get very competitive here." Rory took a sip of her beer, trying to look like a serious authority figure who wasn't just making things up.

Jess shook his head. "I still don't believe you. But on a completely unrelated note, where are the bathrooms here? Just in case I need somewhere to hide later on."

"They lock them during karaoke," Rory said, trying to keep a straight face. "If your name is on the list you have to sing, no exceptions. We take it very seriously." But even though she was trying to act serious, it was nice to be able to take a break and hang out with someone new. The whole time they had been sitting and talking, Rory hadn't thought about her job once.