A/N: Everything up to the middle of the fifth season happened. Rory never dropped out of Yale, Jess never came, etc. Luke and Lorelai are getting married though.

Promising Assumptions

Jess was on his way back to Stars Hollow to keep a promise he made to Rory when they were seventeen.

Flashback

Rory and Jess were walking down the streets of Stars Hollow. Rory curiously asked, "Jess, what do you really want to do with your life? You know what I want to do; now it's your turn to answer me. "

"I don't k-" He started to reply when Rory cut him off.

"And don't just brush it off and say "I don't know" or anything like that. Really answer the question."

"I'll live where I live, I'll work when I ne-" Rory cut him off again.

"You've given me this response before. If you had to do something with your life, what would you do?"

"Write."

It was as simple as that. Rory didn't need anymore of an answer. She understood more out of that answer than anyone else would.

"Okay, just one more thing."

"Shoot."

"Don't forget about me when you become a well-known author."

"Never." He said and gave her a peck on the lips. "Well, what about me, when you become Christianne Amanpour?"

"You are not easy to forget." She said with a chuckle.

"True."

"What are you gonna write about?" She asked.

"I don't know. I guess whatever comes to mind. Whenever I feel an impulse to write, I just will. Whenever I come across something or a situation that inspires me, I'll write."

"See you sound like an author already."

"No I don't."

"Yes you do. It comes naturally for you."

"The only problem is, you can't seem to get it out all the time. To me, it seems like you want to say something in a certain instance, but you just don't. Why?"

"I don't know, really. Maybe it's fear of judgment."

"Why do you assume people would judge you?" Rory asked, completely taking advantage of the rare occasion that he was coming out of his shell.

"I don't know, it's just an assumption."

"Well you know what happens when you assume."

"Yeah I do." He said, smirking.

End Flashback

Jess sat in his car remembering that day. He remembered everything about that day. It was a cloudy autumn day. Rory had just gotten back from school and he went to the bus stop to wait for her with coffee and a cherry Danish, considering that day was Danish day. They walked down the town square and sat on one of the benches and that was where the conversation took place.

Jess's book had been published a month ago and was at the top of the best seller list and had been reviewed by big papers. The New York Times, The LA Times, The Chicago Sun Tines, The Chicago Tribune, and The New Yorker, to name a few.

He arrived at her house in Stars Hollow and knocked on her door. Lorelai answered. "Jess? What are you doing here?" She asked.

"I'm here to see Rory, is she here?"

"Actually, she is at work right now, but she'll be here a little later."

"Oh, okay thanks anyway." He said ready to leave.

"Jess, wait."

He turned around. "Yeah?"

"You wanna come in?"

"I guess. I've got nothing else to do." He said and walked into the Gilmore residence.

"So how have you been?" Lorelai asked.

"I don't mean any disrespect or anything but why are you being so nice to me?"

"I figure because Luke and I are getting married that I should start trying to get along with you because we are bound to run in to each other."

"True. And to answer your previous question, I am doing pretty well."

"You wrote a book. Congratulations on that."

"Thanks."

"And I actually read it!"

"You did."

"Yeah, since I'm gonna be your aunt soon, I thought I should sort of know about you. That sounds weird, right? Okay, forget anything I just said."

"No it's okay. Did you like it?"

"Yeah, I did. Your writing is so, I guess it just sounds like you."

"Really?"

"Yeah."

"How are things with you and Luke?"

"Good, we are in the process of planning the wedding so I'm pretty busy with that and work."

"Good for you guys. Everyone knew you and Luke would end up together sometimes."

"Apparently. Did Luke tell you that Kirk actually started a bet on when Luke was gonna ask me out?"

"No he didn't, tell me more."

"Well everybody put a month on a calendar and some people put specific dates! That had been going on since Rory and I moved here!"

"You're serious?"

"Yes!" Lorelai exclaimed and Jess chuckled.

For the first time, Lorelai thought she was genuinely bonding with Jess.

Just then, Rory came barging through the door, "Mom, I think I'm gonna have to break up with Logan!" She said from the foyer.

"Rory-" Lorelai said trying to stop her because Jess was sitting there with her, hearing everything.

"No, his constant partying and drinking drives me insane and we don't talk at all! We just party and stay out really late and get drunk, no excuse me he gets- Jess." She said stunned when she entered the room Lorelai and Jess were talking in. "Jess, what are you doing here?"

"I came to talk to you, but I see you want to talk to your mom, so I'll come back some other time." He said getting up from his chair.

"No stay, I'll talk to mom later."

"Ugh, I'm hurt!" Lorelai said jokingly and dramatically and left the room.

"Can we go somewhere?" Jess asked.

"Yeah, let's go to the bridge."

"My thoughts exactly."

They went to the bridge in somewhat of an awkward silence. When they arrived, they sat cross-legged facing each other.

"I have something to tell you incase you don't already know." Jess said.

"Your book, right?"

"Yeah."

"I read it, it was so you."

"Your mother said the same thing."

"She did? Wait, you talked to her? Civilly?"

"Yeah and I think we are going to get along better now."

"Good. So why else are you here?"

"I'm keeping my promise."

"What?" She thought about it for a moment and then remembered. "Oh yes." Tears started welling in her eyes. She embraced him and they stayed like that, both not wanting the moment to end.

When they both let go, Rory said, "I've missed you."

"I've missed you too, Ror. I didn't believe I could do it until you and I talked that day when we were seventeen."

"Honestly?"

"Yeah."

"Can I tell you something without you getting mad?"

"Yes."

"I assumed you would forget about our promise."

"Well you know what happens when you assume." He said.

"Yes I do." She said smirking.

Fin