Rory Gilmore was living her life exactly how she had always intended too. She had lived in New York with Paris and Doyle ever since the campaign trail ended two years ago. They had a tiny apartment, but it felt just like when they had lived together in college. She loved everything about her life. After the campaign ended, Hugo had asked to keep her on as a permanent writer. She got to write about a huge variety of things, and the fact that Hugo had seen the changing landscape of journalism and got out ahead of it was just amazing to her.
While her career evolved, so had her personal life. She eventually got over Logan, though it had taken a long time. About a year after the breakup, she had run into Jess. They beat around the bush for a bit, but then he finally asked her out. When she accepted, they took their time. It had been fun, but, eventually, they both realized that they weren't right for each other. They had quite a bit in common, but it just wasn't the right fit.
Rory knew she was trying to please the younger version of herself that had thought they were perfect for each other. When she was younger, she had thought that once Jess grew up, everything would work out. Falling for Logan had been completely unplanned, and it blindsided her.
So when she reconnected with Jess after she got over Logan, there had been an expectation that everything would finally be perfect between them. The realization that she had been holding onto the idea of them for so many years and it was wrong had crushed her almost as much as when Logan left.
Picking up the broken pieces of her younger self's heart had been hard. The upside, though, was that she could finally let go of that particular idea. After that, she had thought a lot about dating and what she wanted for herself. After all of her prior relationships, she realized that she desperately needed a break from all of that. She was tired of the serious, all-in, all-consuming relationships and was ready for some fun. She wanted flings and one-night stands. To hell with feelings, time for fun.
It had taken a little getting used to. On the campaign trail, there wasn't a lot of time for socializing, except with the other people on the bus. There had been one guy that was interested, and she finally accepted on the grounds of it being casual. When that ended and she settled in New York, she started going out more. She reconnected with most of the LDB gang that she had been around in college, minus Logan of course.
Finn had always stayed in touch and became an even closer friend. They went out to the bars often and, one particularly drunken night, even been each other's one-night stand. The next morning, when they realized what they had done, they had both tried to let the other down easy. After having a good laugh, they had promised to put it behind them and preserve their friendship instead.
Yes, her life was good. She had her friends around, loved her job, and managed to have a whole lot of fun living in New York City.
One Friday, she had taken off a bit early that day and was talking to Finn on the phone. They were trying to decide what to do that night when another call buzzed through on her cell phone.
"Hold on Finn, I'm gonna see who this is."
"No problem love."
She switched to the incoming call, "hello?"
A woman answered back, "I'm calling for Miss Rory Gilmore?"
"This is her."
"Please hold for Mitchum Huntzberger," the woman responded.
Rory's jaw dropped and her eyes went wide, "I'm sorry what?" But it was already too late, she heard the hold music.
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It Was Never Really Goodbye - Gilmore Girls
FanfictionLogan told Rory goodbye at her graduation, and he meant it. Didn't he? She wouldn't compromise for him so he couldn't for her in the end. He moved to California, and she hit the campaign trail. Their lives moved in separate directions, and they...