A/N: Main parts of story I want to cover because I despise a lot of the events that occurred in the Rory/Jess plotline.1) When Dean broke up with Rory, they never got back together, but Dean still wishes to be with Rory; 2) At no point in this story will Jess leave. PS – I don't have a great understanding of the relationship and its timeline except from what I have gathered from reruns of the show and multiple fanfictions. I apologize for any timeline errors, but hey – it's fanfiction. It's my story.
Lane sat in her room doing her trigonometry homework, trying not to keel over at the stench of the food (if you can call it that) emanating from the kitchen, when a tap sounded from the window. Rory's face suddenly appeared and climbed into the room as Lane opened the window. "Hi. What are you doing?"
"Trig. You want to help? You definitely understand this more than me."
"I'm good, thanks," Rory hesitated, not sure how to approach the reason for why she came here. "Listen, I need a favor to ask of you."
"Sure, anything. Need to borrow another CD? Music advice, an ear to talk about Jess?" Lane wondered. She noticed how Rory looked apprehensive and shuffled her feet. When Lane mentioned Jess, a blush crept into her cheeks.
"Not necessarily. I need you to go to Hartford with me tomorrow to figure some things out. It would be easier there because of the lack of privacy factor in Stars Hollow. And this is something that is big and needs to be kept secret. Under lock and key. Got it?" Lane began getting nervous. Rory was never like this.
"If you want me to help, it would be easier if I know what I am dealing with. Just the gist of it anyway." Rory tensed, knowing that this was going to occur. Rory could barely even handle it, let alone vocalize it. Just tell her, it'll be like ripping off a Band-Aid. Quick and easy.
She inhaled deeply before mumbling, "Jess and I slept together over spring break, and now I think I might be pregnant. I need you to go to Hartford with me to buy a test." Silence filled the room. Lane could barely think and sat down on the bed, her face frozen in shock.
"Oh my God. Wow. That is just…wow."
"Yeah."
"I'll be at your house tomorrow. I'll say I'm going to the mall with you."
"Thank you," Rory whispered. "Remember to-"
"Not tell anyone, not even Jess or your mom, or anybody. Not even Pierpont. I promise. Now get out of here before my mom hears you." She turned back to the window, which Rory began climbing out of onto the roof.
"And Rory?" Lane said. Rory turned back around with a silently asking Lane "What?"
"I'm glad you told me, and remember that I will always be there for you."
"Thank you so much Lane. You have no idea how much that means to me." Rory replied before descending the tree and walking to Al's to pick up dinner.
As Rory disappeared from sight, Lane walked back to her desk. "Stars Hollow will be the death of me one day." She muttered as she went back to her homework.