A/N: Who wants a new Literati fic? Don't worry, it won't stop me regularly updating my current fics, I just... I need to be sharing this now, so I'm going to. It'll be updated as and when, no schedule, and honestly? It's such a wacky idea I don't actually expect anyone to read it or care about it, but hey, posting it anyway! lol

Disclaimer: All recognisable characters from Gilmore Girls belong to Amy Sherman-Palladino and other folks who aren't me. Storyline based on the movie musical 'High Society', which itself was based on the movie 'A Philadelphia Story'.


May 2003

Rory Gilmore ought to have known it could never last. If things seemed too good to be true, that was because ninety nine percent of the time, that's exactly what they were. She supposed that she had hoped they were that rare one percent, her and Jess, but apparently she was wrong.

When Jess Mariano first came to town, Rory had been intrigued. She had heard so much about Luke's nephew but never met him. The dark, mysterious, brooding boy from NYC proved to be much better looking than Rory had expected somehow, and so amazingly well-read! They just seemed to have so many interests in common, from books to music, movies, and so much more. The only major difference between them was that Jess seemed to be drawn to trouble, and Rory had always been such a good girl. It made them an unlikely pairing in most people's eyes, but Rory couldn't think of anything more perfect than getting closer to Jess, and he had no problem with that at all.

She hadn't really dated before. No, Stars Hollow's little Rory Gilmore had never had a boyfriend, but pretty much from the get go, she knew she wanted Jess to be the first, and potentially the only.

It was rocky off and on. Rory's mother, Lorelai, didn't much care for Jess, and though Luke loved his nephew dearly, he also looked upon Rory as a daughter. It made him protective and at times, that left no-one in Jess' corner. Rory's grandparents never really liked the hoodlum either, and the townsfolk were determined to see only his less-good side.

Rory always insisted no-one knew Jess like she did. To this day she still believed that, and yet Jess had gone out and proved that for all she knew of her boyfriend, it wasn't enough. He left, more than twenty four hours ago, and without a word of goodbye, though they had dated for more than eighteen months. Rory thought it ought to mean something to him, but maybe she was wrong.

Jess had recently revealed that he was flunking out of high school through poor attendance and couldn't take her to prom, but Rory couldn't believe that alone was his reason to run. She blamed herself. She must have been such a terrible girlfriend if he couldn't talk to her, couldn't even bear to say goodbye. She even considered it was because she just wasn't good enough when finally she felt ready and she and Jess had sex. It only happened once, just a few days before he left. Rory never talked to her mother about it in the end, because she knew Lorelai would use it against Jess in the worst ways. She just didn't want to hear that.

Rory knew she wasn't blameless for this relationship falling apart. Sat in the darkness of her room all alone, going over everything that had happened, she knew she made mistakes. That didn't change the fact that Jess was wrong too, running out on her without a word. People who loved each other like they were supposed to didn't act that way. Not that Rory had been too fast to tell him she loved him. Maybe she should have made it clearer; it might've encouraged him to do the same. It didn't take long for Rory to realise that much of the time she had been telling Jess where he was going wrong in his life, trying to make him want to better himself. It was supposed to be a supportive thing, but maybe she had just pushed too hard.

Regardless, Lorelai was now blaming Jess for everything since the world began, and most other people seemed to agree. Luke, Emily and Richard, the folks in town, they all took the time to tell Rory how much better off she was without her dead-beat boyfriend. Rory didn't feel better off. So much for plenty of fish in the sea and all the other old clich├ęs, Rory couldn't bear the thought of dating anyone but Jess. Of course in time she probably would, but right now her heart was broken, and felt as if it might never be repaired.

To Be Continued...

A/N2: I hope to post Chapter 1 tomorrow, which will jump forward to June 2008, and then the fun really begins ;)