Title: Second Chances
Rory Gilmore walked into the crowded hallways, full of high schoolers from Chilton prep school, holding documents in her hands. The familiar scent of polished floors, and even seeing her almost stepdad to be Mr. Madena. Rory walked right up to him, and they started having a conversation. He was wondering why Rory was back and she told him why. It has been eight years since she graduated, but somehow, everything feels the same.
Rory came back to Chilton to talk about her career as a famous journalist. She went to Yale for four years and then became famous for one of her investigative stories. Rory felt a little odd being back at Chilton, walking through the halls of her teenage years, feeling nostalgia. She even saw her pictures on the school wall, becoming one of the most important and famous people from Chilton. Memories of old friends began to swirl around her and also some unpleasant memories as well.
"Hey, Mary! Haven't seen you in a while."
That voice. Rory's heart skipped a beat as she turned around. Standing right behind her, was a very tall guy, with his trademark smirk, Tristan Dugray. With his golden hair and bright white smile, then she remembered who he was. She thought he was still very cocky, looking like he was still causing a lot of trouble.
Rory finally says hi to him. "Tristan," she said, her voice sounded a little irritated. "I didn't expect to see you here" he says.
"I could say the same thing to you," Rory says, walking closer to him. "What brings you back to Chilton?" "Finishing high school."
Tristan rolled his eyes. "No actually, I finished high school at a different school when I left here. But I am here to give a presentation about my job."
"Oh really" Rory exclaimed. "I am as well."
Tristan chuckled. "I have a major company and I'm a sponsor of a new technology initiative they're starting. The headmaster wanted me to give a presentation on how I own a major company."
Rory thought that after college Tristan went into finance, but she never expected that he would be involved in a major company and have tech investments. She remembered seeing his name on television a couple of weeks ago, seeing how he turned up.
"I never thought in a million years I would see you here," Rory said. She hadn't seen Tristan since he got in trouble and had to leave high school. He had gone to a boarding school in a different state, and that's when she never saw him again. There were times, though, when she'd think of him, after she broke up with Dean, Jess, and Logan. There is lots of tension between them and it is a little awkward.
"So, how's life of Rory Gilmore?" Tristan asked, leaning casually against the wall. "Still taking over the world one article at a time?"
Rory smiled. "I've been very busy, traveling to different places to give presentations.
He nodded, and for a moment, there was a lot of silence between them. Rory's eyes studied Tristan and Tristan's eyes studied her. They both could feel the weight of their gaze on each other, and Rory wanted to know what he was thinking.
"You look better than ever," he said. Rory was surprised but said, "thanks you too."
Tristan smiled at her, a real one and not a smirk. In his smile Rory saw something different, she saw something that she thought she would never see in him. He wasn't the cocky, rude boy she remembered from high school; he was someone different. He'd grown up.
Tristan began to speak "I know we didn't get along quite well in high school, but I want us to be on good terms. I wasn't the easiest to deal with and definitely not the nicest."
Rory laughed. "I certainly agree."
"Yeah, I deserve that. But I'm truly sorry about how I treated you. I was a jerk to you" Tristan says.
Rory was very surprised that he apologized for everything that happened in high school. She'd spend so long thinking about Tristan as a part of her past, she forgot all about him. Yet there he was apologizing for his mistakes back then.
"It's all good, we were just kids," Rory said.
"True," Tristan agreed. "But that doesn't mean I didn't know how I felt about you."
Rory's breath got caught in her throat. She did not expect that to come out of his mouth. She looked at him, looking deep into his blue eyes, and saw something she had never seen before.
"I don't know Tristan..." Rory began, I don't know how to respond to that. Rory thought of all her past relationships with Dean, Jess, and Logan and thought about how she loved them all and then they were gone. Now there was Tristan, standing right in front of her, after all these years, bringing feelings that she never knew existed.
"Let me take you out to dinner," Tristan said, cutting through the awkward silence. "No pressure, just dinner, we can catch up, and then see where things go."
Rory hesitated. But there was a part of her that wanted to go to see if things would work out between them. "I will go on one condition; we have to go to my favorite restaurant."
"Okay, that's fine."
Dinner with Tristan was amazing. Much easier than Rory anticipated. They met at a cozy restaurant in Hartford. Rory thought she knew Tristan but to her surprise, she had a great personality and a great sense of humor. He was thoughtful, asking her about her career, her travels, and was a great listener. This dinner changed Rory's perspective on Tristan, realizing that he's a good person and a good guy.
They talked all night; about stories they had shared. As the evening went on, Rory found herself laughing more than she had in a very long time. Tristan was charming, but he was also kind in a way that was very new to Rory.
"So," Tristan said as they finished their meal, "was this a terrible idea?"
Rory looked at him, "No, definitely not."
"I'll take this as a win," he said.
Rory smiled, but inside of her, her mind was racing. She asked, "do you want to have dinner again tomorrow?"
Tristan was pleased "Yes definitely, but this time I will take you to my favorite restaurant."
Rory and Tristan, walk out of the restaurant together.
As time goes on, Rory and Tristan spend more and more time together, eventually becoming a couple. They spend quality time together and eventually move in together. They live a happy life together, and then Tristan says, "Will you marry me?"
Rory squealed with excitement. "Of course I will marry you, I love you."