So I'm struggling with the most pivotal chapter in my story Yales, Yachts and Other Distractions, and this was one of two unrelated plot bunnies that popped into my head recently. I like to think Jess visited Stars Hollow when Rory wasn't around. Stuff had to have happened off-screen, you know! This was one of several things the Jess storyline left untouched, so I decided to play with it.

Disclaimer: Owning nothing now, but one day… I'll own my own car!

Apology

This town would be the death of him, of that he was certain. The manufactured appearance of 1950s charm with the totalitarian leadership of a 1950s dictator. At least the Russians didn't run around in cardigans, they had style. Visiting this place was not on a whim, or just to check out the new displays celebrating the coming summer months. No, Jess Mariano was here on business that was terrifying and possibly suicidal.

For the first time in his adult life, he was going to have a conversation with Lorelai Gilmore.

Over the years, at least after the painful surgery that had his head removed from his ass, Jess had righted a lot of the wrongs he had made. He could remember at least two separate occasions in which he and Luke had shared something that he would reluctantly label heartfelt, and the bridge between him and his mother had been diminishing rapidly after her wedding. TJ was an idiot who didn't believe in laps, but he loved Liz and Jess was glad that everything was working out for her. In fact, the primary reason for his visit was to meet his half-sister, who was given the unfortunate name of Doula.

Still, all the pleasantries with his mother were finished and now he was only faced with what was probably going to turn out to be certain doom. He was pretty sure the memories this woman held of him revolved around stealing bracelets, crashing cars, breaking up committed relationships and eventual running away and breaking of her only daughter's heart. There was a very good chance she was going to come at him with a knife, so he only hoped that Luke had put in a few good words with her while they were dating.

With a deep breath and a muttered 'I'm a masochist', Jess knocked on the front door.

"Kirk, I told you I'm not giving you the- Jess. Are you lost?"

"In Stars Hollow? What, I took a wrong turn by the market and forgot which of the two streets in this town I was heading for?"

"Wow, you're just as unpleasant as ever." Bad move with the sarcasm, clearly. Lorelai looked a few seconds from closing the door in his face.

"This is so not the way I wanted to start this conversation. Hell, even 'I'm the one who organised Firefly's air dates' would've been met with less scorn."

Lorelai tried not to smile at this little quip. "That's only because I'm not Joss Whedon. Do you want to come in or should we just let the whole town see us talking? You realise it's probably one of the signs of the apocalypse, and Kirk just wouldn't be able to handle it."

"If I see any flaming horses you'll be the first person I tell."

He walks inside after her, and notices how different and yet exactly the same the whole place was. It's clear that there's been some remodelling and someone male had lived here, but for the most part it's remarkable how much of Lorelai remained in the house. It was still quirky and random as always, just with a better TV and more legroom. He tried not to think about Rory's influence on this place, as thinking about her in general didn't put him in the best frame of mind these days.

"So, what's up?" Lorelai asked tentatively. She was trying her hardest to be non-judgmental towards Jess after all the hyping up of the young man she endured while she and Luke were dating. Still, this was the boy (man now, she figures) who fractured Rory's wrist as well as her heart. It had always freaked her out how connected her daughter was to this boy (man) so she wasn't exactly disappointed when he left. Relieved was probably a better word, because it meant her daughter remained innocent until sleeping with a married man a year later. Which was surely better than sex with the town badboy she was in a committed relationship with, right?

"This is really hard for me and I suck with words unless I'm writing them, so it would be really cool if you just cut me some slack, okay?" Lorelai nodded her consent, and he continued. "Throughout my life I've done a lot of stupid things, and I've hurt a lot of people. Some of them I set out to hurt because I was an ass, and some I hurt inadvertently. But there are some people who I was a jerk to and they didn't deserve it. People like Luke and Rory deserve all the apologies I could ever hope to provide, and I think I owe almost as many to you. At first you were just trying to help, to give me some perspective but I wasn't having any of that. So, sorry for stealing the beer and implying that you wouldn't do anything for someone without getting something in return. Then all the things I put you through as a mother, with Rory… Some of those things I'd take back, but most of them I wouldn't. So I'm not sorry a lot of it happened, but I'm sorry for any inadvertent stress or anger I may have caused you. I'm sorry I was always rude, I'm sorry. Just for teenage me in general, I guess."

"I… wow, that wasn't monosyllabic at all."

"Long-winded apologies rarely are."

"You didn't have to-"

"Yes I did."

"You really grew up, huh? I mean, Luke kept telling me you did but I figured we were talking Ted Bundy to Al Bundy, but you straightened yourself out. Then you got my girl to come home, I never got to thank you for that."

"She would've figured it out eventually."

"You were the only one who got through to her. We were all saying the same things, but she tuned us all out. Except you."

"Still, it wasn't my finest moment. Let that blonde dick get inside my head."

"Blonde dick? Oh god, Logan. Please don't speak about him around me."

"They break up?"

"Worse, he actually asked my permission to propose to Rory. Came to my house yesterday."

"Huh."

"I was very prepared for you to ask me the same thing today."

"Because that makes a lot of sense."

"It makes more sense than Logan 'my daddy bought me a Porsche and an escort for my sixteenth birthday' Huntzberger."

"You seem awfully fond of your future son-in-law there, Ms Gilmore."

"She's not going to say yes."

"You sure about that? She stuck through him cheating on her, I'm guessing either she loves him or he's drugging her."

"How do you know about… whatever. He wants her to move to San Francisco with him. Something about a house with a tree."

"California? Unless you're a health nut or chase delusional aspirations of acting there's nothing there."

"She's going to say no."

"You keep saying that."

"He's going to make it all or nothing, and she's going to say no."

"I'm guessing you're making a point of some kind. Care to share it with the class?"

"If you can make me forgive you for being Dennis the Menace to my Mr Wilson, there's a startlingly high chance that you two could get back together."

"You're assuming I want that."

"You called Logan a 'blonde dick'. Jealousy."

"You did too!"

"I'm the mother, I'm supposed to! Plus why would you come and apologise to me if getting back together with Rory was not one of your life goals?"

"Wouldn't want tension between us when you and Luke finally get hitched."

"What? Luke and I aren't even-"

"Everyone knows about the song, Lorelai. Everyone."

The better part of the afternoon was spent in this manner, with the mocking lined with mutual respect. It seemed as though Jess' entry to the lion's den had proven successful, which lifted some of the weight from his heart. Though the apology that was still half-formed was the most important, he knew it would be made right eventually. He owed Rory so much more than he did her mother, but their hurting was mutual. One day they would both apologise for whatever pain they had caused the other, he knew that for sure. The murkier future, the results of this, Jess would contemplate with as much as an open mind as possible. If Lorelai was right about Rory's reception to Logan's proposal, who knew what could happen? For all he knew he was the perfect 'I'm sorry' away from being truly happy for the first time in his life.