Disclaimer: I do not own any of the characters
Notes: This is a prequel of sorts to a Mafia au PrincessaKyla and I are working on. The story takes place around when Rory went to see Jess in New York, except they hadn't met previously. At the start of the story, Rory is still with Dean. Jess lives with Jimmy, Liz was the one that bailed. Also posted on ao3
Rory Gilmore stepped off the pristine chartered bus along with the rest of her Chilton classmates into the chilly New York air. They were on a field trip to see Phantom of The Opera at the Majestic theatre and then write an essay comparing and contrasting it with that of the book. She watched her classmates group off and get their tickets; she of course, was left by herself so she was given the "odd-ticket-out."
Her seat was located away from the rest of her classmates. Rory sighed and headed inside to find her seat. The theatre was a pretty big place, she'd done her research on it before leaving on the field trip. Her seat was the only one up in the rear mezzanine section, thus she had to walk up about 3 or 4 flights of stairs. She began her trek after grabbing a playbill. Halfway up the first set of stairs she ran into someone, having not been paying attention in favor of looking through the playbill. She ended up half sitting on a step. "Sorry!" Rory embarrassedly said.
"It's alright." The person said in just-barely-there New York accent, somewhat amused. They offered a hand and helped her up. "Jess Mariano. And you are…?"
Rory blushed and took his hand."Rory Gilmore." She replied shyly. He was gorgeous, to put it bluntly. He had messy black hair, brown eyes and was dressed in dark wash jeans, a Distillers tshirt and leather jacket.
"Well, it's been a pleasure Rory. Enjoy the show." He smirked and walked down the steps.
Rory watched him walk away before resuming her trek up the stairs. She then quickly headed to her seat. Once seated she calmed down a bit, but Jess was still at the back of her mind. It bothered her a bit, she shouldn't be thinking about another guy when she had Dean! Rory dispelled those thoughts and checked her watch, 10 minutes until show time, with that she pulled out her book, Howl & Other Poems by Allen Ginsberg.
A few minutes later Jess Mariano sat down next to her. "Now who could have known, we'd end up sitting next to each other." He said partially sarcastically, partially playfully.
Rory looked up in surprise, too shocked to really respond. She laid her book on her lap.
Jess continued on. "So clearly you aren't from around here, by the looks of it, some prep school?"
Rory nodded, finally finding her voice. "Chilton Preparatory School in Hartford, Connecticut. What about you?"
Jess shook his head. "I'm not here with a school."
"Wait, so you're skipping?!"
"I'm not missing anything I don't already know."
Rory gave him a look but didn't say anything.
A few minutes passed before Jess spoke again, Rory had taken to looking anywhere but at Jess. "So, Rory. Wanna get out of here?"
"What?! No! I can't leave!" her heart sped up just a bit.
"Come on, you mean to tell me you'd rather sit here than get out and explore the city?"
He had a point. She'd much rather go explore the city with him. 'Wait! No! Bad Rory! What about Dean?' she thought. Rory was quiet a moment too long and her extended silence seemed to be all Jess needed. He took her hand and pulled her up, pocketing her book as well and leading her out to the stairs.
"Jess! I can't just ditch!" 'Can I?' She thought almost helplessly.
Jess stopped, halfway down the 1st staircase and looked up at her with those gorgeous coffee colored eyes. "Rory. How often do you get a chance like this? Come on, it'll be fun! And I promise we'll be back before the show's over. No one will notice."
Rory thought for a moment and then smiled, something about Jess sent her heart racing and gave her butterflies unlike anything she'd ever felt with Dean. "Okay, lead the way!"
Jess beamed and led her down the rest of the stairs, through the lobby, out of the Majestic Theatre and they began their way down 44th street. Rory couldn't be more excited.
Updates soon to follow! Thanks for reading!