A/N: Wow, it's been a long time guys. Sorry about that! This is the first longer fic that I've tried in a regular narrative style and it's been a challenge for sure (not to mention writing about Christmas while wearing shorts!). I think we're getting somewhere, though. I absolutely promise that the next chapter update will not take weeks and weeks (please don't tell me it's been months already...).

December 26th quickly turned into the 27th, which faded into the 28th and the 29th. On December 30th, Rory finally mustered up the courage to give her pro and con lists another shot. After her talk with April she had enjoyed a few quiet hours with her family, eating Al's Chinese food and watching movies until they all started nodding off in the living room. The next day Rory had taken April to the mall where they got manicures and pedicures, saw a movie and spent nearly two hours in the Discovery store. After that Rory had visited with Lane, babysat for Sookie, checked in with Andrew at the bookstore about his new stock, settled a debate with Taylor and his employees about what the January flavor of the month should be, listened to Babette and Patty practice for their next act at K.C.'s and helped Kirk lure Cat Kirk (who was miraculously still living with Kirk) out from under the gazebo. She had kept her days busy and hadn't seen Jess again, except for a quick glimpse of him in Luke's window coming out of Doose's with the tuna for Cat Kirk.

It wasn't that Rory was trying to avoid Jess. He seemed like a perfectly nice guy. The problem was, Rory really wanted to impress him the next time she talked to him. She wanted to be able to say definitively what she was going to do about her job. It was ridiculous, of course. Jess, while technically a future part of her family, was a stranger. In addition to her decision having absolutely no effect on his life, there was no reason to impress him. At some point he was going to go back to Philadelphia and if Rory stuck with her job, she was going to be flying out in a couple of days. Not to mention the fact that Rory couldn't remember ever trying to impress a guy, even when she had dated Dean in high school. Some girls spent their whole lives dressing up and laughing loudly and faking interest in different things to get the attention of boys, but Rory had never done that before and she certainly wasn't planning on starting now. But Jess was the only one who really knew what was going on with her job, and she wanted to show him that she could take control of her life. Any credit she got for taking the reins and turning down Logan's proposal last spring had faded away at a breakfast buffet somewhere in the Midwest.

The pro-con list looked just as depressing as it had when Rory had started it. Had she really put dealing with getting mail as a con? She emailed practically everyone she wanted to talk to. The allure of postcards and care packages from home had worn off around the end of summer. Frustrated, Rory tore the list into eighths and tossed the pieces in her trash can. She did the same with the pro list, without even glancing at what she had written. If she was being completely honest with herself, she wanted to quit. Other than the virtue of it being a paying job, she didn't think there was anything good about her job anymore. But part of being honest with herself was admitting that she was completely terrified at the idea of not having a job anymore. After she didn't get chosen for the Reston Fellowship her confidence had been shaken to the core. When she was offered the campaign job she had breathed a huge sigh of relief, safe in the knowledge that at least one person thought she was good enough. What if no one else did?

Tomorrow night they were all going to her grandparents' house for New Year's Eve. By midnight tomorrow, Rory decided, she would make a decision. When the ball dropped at midnight, her new year's resolution was either going to be to learn to embrace her job or to find another job as quickly as possible. Either way though, Rory was going to feel like she was giving up. Quitting her job was obviously giving up on the job, but sticking with the job meant giving up on what she really wanted. It was settling. Rory had never thought of herself as someone who would settle for anything. She worked to get into Chilton and once she was there, she worked harder than she even thought possible to get into Yale. After taking a break from Yale her junior year she could hardly say that she never gave up, but she could at least say that she had never settled for anything that she didn't truly want. Even in her time off from Yale, she hadn't settled for just loafing around her grandparents' pool house all day; she had gotten a job with the DAR. But sticking with this job meant that she was settling for being unhappy, and that meant she was giving up.

Logically, Rory knew that most people in their early 20s didn't have their lives together and that most people were struggling to get by, working jobs that they didn't necessarily love while they worked toward something better. The problem was, she didn't know a lot of those people. Lane had a family that she loved, Paris was doing scarily well in med school and even Lucy and Olivia emailed her occasionally about the latest fantastic gallery opening they had been to or the newest cute guy they were dating. She had never been the type of person with a wide net of friends, and the friends that she did have were happy in what they were doing. No matter what was average, Rory could only directly compare herself to her friends and she felt extremely left out. Her friends were happy, and she was just floating along.

It was even more difficult when everyone talked up her job. It made her feel guilty for not appreciating it more. If it was so "glamorous", as April would say, then why didn't she want it? Rory shook her head, as if she could actually expel all thoughts of her job that way. For the first time over her break the house was quiet, with Lorelai and Luke at work and April at a friend's. Even Paul Anka was asleep. The silence was driving her crazy. She needed a distraction. Before she could overanalyze another part of her life, Rory pulled up the recent calls on her phone and dialed Jess. He answered on the second ring.

"Hello?"

"Hey," Rory said. "Hi. It's Rory. We met for coffee the other day." As soon as the words were out of her mouth she regretted calling him. They didn't really know each other, but he probably remembered the girl he had seen on three different occasions within the last week.

"I remember who you are," Jess said with a laugh. "What's going on?"

"Well, the holidays are almost over so I'm sure you're going back to Philadelphia soon and I could really use a break. I'm going to my grandparents' for a party tomorrow night, but do you maybe want to do something later today? If you're not busy. There's this bar that's doing karaoke night and a bunch of people from town that I know usually go and these two women always do a really long set and it's kind of funny, so I thought you might want to check it out. I'll probably go either way."

"Are you asking me out for a drink?"

Rory cleared her throat, feeling heat rising in her face. "Since the karaoke is at a bar and they serve drinks, we could get drinks."

"Remember when we were talking about your job the other day and you kept trying to talk yourself into liking it? You were just bullshitting. That's part of your problem right there."

He was right. Of course he was right. With an outside perspective he could probably judge the situation better than anyone. Rory had been talking herself in circles for months now, avoiding the card concrete questions, and it was going to come to an end. She still didn't know what she should do about her job, but she could start putting a stop to all the bullshitting right now. "Jess?"

"Yes?"

"Would you like to get a drink with me tonight?"

"Sounds great. I'll pick you up at 8."