Title: The Tales of a Broken Heart

Author: Michaelover101

Rating: M... just to be safe.

Summery: Girl gets conned into going to Martha's Vineyard, girl meets boy, boy meets girl, boy and girl date, boy goes to Fiji, girl goes to Yale... only broken hearts can follow. PDLD

Beta: Flynn

Disclaimer: Doesn't matter how hard I squeeze my eyes shut... Finn, Colin, Logan and Tristan do not belong to me...and unfortunately neither do any of the other GG characters.

Notes: This is set after Rory's graduation. Emily has conned Rory into going to Martha's Vineyard instead of Europe with her mother. The story will take place in different and important aspects of Rory's life at Yale... with lots of differences and more Finn!


Part 1: Anything Is Better

"Sliding down an unwaxed banister... in a thong." Rory said into the phone as she walked down the beach. She heard her mother laugh.

"That was a good one, getting brain freeze on a below zero day."

"Watching a Pong tournament." Rory said.

"Dating Kirk."

"Not fair."

"Why not? That's better than going to Martha's Vineyard with my mother."

"Yes, but Kirk liked you, so it's not fair that you say it. I can't date my future daddy." Rory teased.

"Okay, it happened once. Once, Rory, let it go. That ship has sailed."

"He still gets confused when I call him daddy." Rory laughed.

"He still gets confused when people start kicking him when he has a "kick me" sign on his back."

"True, true."

"I miss you, babe."

Rory smiled sadly. "I miss you too."

"I can't believe my mom did this. 'We paid for Chilton, Lorelai'; 'We're paying for Yale, Lorelai', 'We deserve one summer with our granddaughter, Lorelai'." Lorelai said doing the impressions of her mother.

"Yeah, not fair using that guilt trip on us." Rory said.

They had gone to their last Friday night dinner before their big trip, when her grandmother had started telling them about the house they had gotten for the summer and how much fun she had every year. Rory had made the mistake of saying how fun it sounded, and Emily Gilmore got a gleam in her eyes.

"Well, there's always next year," Lorelai said with a sigh

"But it was suppose to be this year," Rory said as she put down her bag and sat down on her knees and extended her towel.

"I know," Lorelai sighed. "So what are you doing now?"

"Grandma went shopping with some DAR friends and grandpa locked himself in his study, so I grabbed a book and I'm now on the beach preparing to read."

"So the usual?"

"The usual."

"God, I hate my mom for doing that, Rory."

"I know," Rory said with a sigh. "Next year."

"Yeah, call me later?"

"Yeah, later."

"Going without Luke's coffee." Lorelai said.

Rory smiled. "You really do miss me, don't you?"

"Like the sky misses the sun, babe."

"Unbelievably corny, but I'll let it pass."

"Good, love you, babe."

"Love you too, mom," Rory said as she hung up. She got out her book of the moment 'A Million Little Pieces' by James Frey and laid on her stomach, placing her sunglasses down on her eyes before opening her book and starting to read where she left off.

She wouldn't have minded coming to Martha's Vineyard with her grandparents, but they had known that Rory and Lorelai had had the Europe trip planned from the first time she set foot in kindergarten.

"Four!" Rory heard someone yell. She frowned and looked up from her book just in time to see a blonde guy tripping in the sand and land on her. She winced and dropped her book.

"Ow." She heard the guy said as he started to move. He got off and Rory sat up slowly, her back had broken, she thought, she was going to die. Wait, no, she heard her back crack and she winced.

"Jesus." She muttered as she stood up.

"I'm so sorry, my friend threw the Frisbee too hard and, well, they yelled 'four'."

"If this is some lame attempt to pick me up, it's not going to work, you're heavy and I think you cracked a rib. And 'four' is a golf reference, thus why I didn't move." She said stretching her back.

"Huh, my ribs don't hurt," she heard him mutter.

"Yeah, but mine do."

"I am really, really sorry; I swear this is not some lame attempt to pick you up... Mary?"

Rory frowned. 'Don't look up, don't look up." She chanted in her head, but her eyes betrayed her and she looked up. Sure enough, the same blonde hair and blue eyes that taunted her during her first year of Chilton were standing right in front of her; and without a shirt no less.

"Tristan." She said with a roll of her eyes. "Figures."

"Wow, it's really nice to see you." He said as he went to hug her. Rory backed away and they danced around each other, until they settled on an awkward hand shake. "We weren't really on hugging terms when we left, were we?"

"No, I don't think we were," she said.

"I really am sorry I fell on you, but my friends and I were really playing Frisbee, and my friend is a jackass and threw it too far."

"It's fine, I'll be sure to send you my medical bill." She teased propping her glasses on her head.

"You do that; so what are you doing here?"

"My grandparents have a house on the beach... you?"

"Hanging out with some friends, I haven't seen them in a while. Here, get your stuff and I'll introduce you."

"No, Tristan, it's fine. I was actually heading back."

"No, come on, let me make up my two years of being a jerk, I swear I'm reformed," he said with a smirk.

"DUGRAY!" Someone yelled from behind them. Tristan turned back and held up a hand. He turned back to Rory and smiled.


"Just for a few minutes, Tristan, I really do need to head back."


Rory sighed as she folded her towel and put it in her bag, along with her book. She stood up and put the bag on her shoulder and looked up at Tristan uncertainly. He smiled back and led her towards his three guy friends who were standing around, all without a shirt.

"So still a Mary?" He whispered.

"Why do you ask?" She asked with a glare.

"You're blushing."

She shoved him with her elbow. "You said you were reformed."

"Ah, but the old Tristan you know and love pops up every once in a while." He waved his friends over and they came jogging up to him.

"Hey," a blonde said. "Who's the girl?"

"This is supposed to be guys' summer, Tristan." A brown haired guy said with his arms over his chest.

"She's cute." The other brown haired guy said, he had an accent.

"Guys, this is Rory Gilmore, she went to Chilton with me until I got shipped off. Rory, these are my friends, Logan Huntzberger," he pointed to the blonde; "Colin McCrea," he pointed to the brown-haired guy. "And Finn Rothschild," he said pointing to the guy with the accent.

"Nice to meet you," she said with a smile.

"So you're the Gilmores' granddaughter?" Logan asked.

"Yeah, Emily and Richard's." She said uncomfortably.

"The prodigal grandchild." Colin said with a teasing voice.

"You're going to Yale, right?" Finn asked.

"Um, yeah, that's what the Pro/Con List said," she said shifting her feet in the sand.

"Pro/Con List?" Tristan asked.

"I made a list." She defended. "It's not that crazy of an idea. It's hard picking between Princeton, Harvard and Yale."

"All three, impressive." Finn said with a smirk. Rory blushed.

"So you made a Pro/Con List?" Tristan asked.

"Shut up, Tristan," she muttered.

"Well, lucky for you, I'm also going to Yale." Tristan said.

"That's nice, why?"

"My girlfriend," Tristan said.

"Are you serious, Tristan DuGray has a girlfriend?" Rory laughed. "Wow, I think the Earth just stopped moving." She teased, causing the other three to laugh.

Tristan rolled his eyes. "I've been dating her for almost two years. It's not that big of a deal."

"What's her name?" Rory asked curious.

"Stephanie Merdock." Tristan answered.

"She's a friend of ours," Logan said. "They met at one of those stupid social gatherings our parents plan. Tristan was home for a break in military school. They screwed each other, and, well, they've been screwing each other ever since." Logan said with a smirk.

"Hey, hey, that's no way to talk in front of a Yale woman." Tristan said covering Rory's ears. Rory pushed him away with a laugh, then felt her phone vibrating in her bag. She got out her phone and looked at the number. It was long distance. She sighed and answered.

"Hello?" No answer, as usual. "Jess?" He had called at her graduation, she had told him she had loved him and he hadn't called again. Till now. She thought she was over him. "Jess, you've got to stop." No answer.

She bit her lip hoping he'd say something, then sighed. "Look, if you're not going to say anything, then don't call." She backed away from the group a bit, wanting a bit of privacy. "I said everything I needed to say when you called at graduation, I need you to stop calling. I can't get over you if I keep expecting you to call, I don't want to expect you to call. I don't expect anything from you anymore, so just, please, stop."

She thought she heard a faint 'I'm sorry' before the dial tone hit her ear. She took the phone away from her ear and stared at it for a minute before hanging up and putting it in her bag.

"Hey, you all right? Tristan asked, coming over to her. She turned and sent him a smile.

"Fine," she replied. She looked back to her phone and sighed. "I actually have to go."

"Oh, come on now, love, you aren't going to let one silly little phone call mess up our fun." Finn said with a teasing voice. Rory sighed.

"I just really need to…": She covered her face and let the tears pass.

"Okay, you are really not all right." Tristan said bring her closer to the group. She pulled away

"I'm fine," she said wiping her tears. She felt her phone vibrating again and she sighed. She just hoped it wasn't Jess again. She looked at the caller ID and frowned, but answered.

"Didn't we just talk?" She asked.

"Is that the way you talk to the woman that gave you life?"

"Yeah," Rory said.

"Are you all right?"

"I'm fine."

"You sound like you've been crying."

"Nope, no crying."

"It's Jess."

"No, it's not Jess."

"Are you sure?"

"I'm positive, you called?"

"Right, watching five straight hours of the Brady Bunch Variety Hour."

"I thought you liked that show and I don't want to play anymore."

"I like that show, but you don't like that show."

"Mom, going to Chilton with Paris is better than coming to Martha's Vineyard with Grandma and Grandpa."

"Okay, okay, you win. Are you sure you're all right?"


"So what's happened in the past half hour since you hung up on mama?" Lorelai asked.

"Nothing. I read, Tristan fell on me, I met his friends, then…" Rory bit her lip, then continued. "You called and that's about it."

"Tristan? Do I know him?"

"DuGray." Rory said.


"Blonde, blue eyes."

"Yeah, so were the Nazi storm troopers. Wanna narrow that down?"

"Went to Chilton."

"Nope, not ringing any bells."

"Called me Mary." Rory said.

"Oh my god! Bible boy fell on you."

"I think he cracked a rib."

"The irony, oh, the irony."


"I mean this guy loved you in high school."

"He did not!" Rory protested.



"Oh, you are so innocent."

"Oh, shut up." Rory said with a frown and crossed her arms over her chest.

"You're pouting."

"Am not!"

"Oh, you're pouting, I have won."

"You didn't win, there was nothing to win, and this conversation has gotten ridiculous!"

"All our conversations are ridiculous."


"Are you sure you're okay?"

"Mom, stop."

"Right, it's just, you didn't wallow."

Rory sighed. "Why didn't you make me?"

"What?" Lorelai asked. Rory could hear the confusion.

"It's just when I first broke up with Dean, you practically begged me to wallow, you put it on the list and everything."


"But with Jess… you haven't said anything."

"Well, I know you wouldn't do it just because I told you to."

"I know."

"Do you think I didn't tell you to wallow over Jess because I didn't like him?"

"Sort of."

"Rory, I hated Jess, he wasn't right for you."

"Gee, thanks."

"But you needed your Christopher, and he was it."

"You comparing my ex to dad isn't helping."

"You needed your bad boy. And Jess was it. But the wallowing thing was all you. Is that why you were crying?"

"I wasn't crying!" Rory protested.

"Sure you weren't, you don't think I know who all those calls are from."

"How did…"

"Jess is the classic guy of call and hang up. It's like a role reversal. You know how you did it to Dean and Lane did it with Dave?"

"Yeah, but we did it because we liked them."

"Yeah, and Jess still likes you, but he feels guilty for leaving you."


"You okay now?"

"I've been okay." Rory said getting irritated.

"Okay, okay, no need to snap at mama. Go enjoy Bible boy and his friends. I'll call you later."


"Love you, babe."

"Love you too." Rory said hanging up and turning her phone off.

"I'm going to ask, but you have to promise not to kill me, are you all right?" Tristan asked with a smirk.

Rory sighed and glared at him. "I'm fine."

"All right."

"So we were planning on going to lunch, love, would you like to join us?" Finn asked. She smiled at him and shook her head.

"No, I'm good; I think I'm going to head home."

"Oh come on, Rory, come have lunch with us." Tristan said. "It'll give us time to catch up."

"Can I take a rain check? I've something I've got to do."

"We're holding you to that." Colin said.

Rory nodded. "I don't doubt that. It was really nice meeting all of you."

"Nice meeting you too." Logan said.

"And Tristan, nice seeing you again."

"Really?" He asked with a raised eyebrow.

"Getting there."

"Good." She gave a wave and started waking down the beach, kicking the sand in front of her.

"She's cute." Finn said.

"That was your Mary?" Logan asked Tristan.

"That was my Mary, the love that will never be." Tristan said with a smirk. "I think she is the only other girl I have ever loved."

"Who's the other?" Colin asked with a smirk.

"Stephanie, and you tell her that, you die." Tristan said pushing Colin as he laughed.

"It's so nice to know you care for my cousin." Colin said with a laugh. They turned back around and Finn watched as she continued to walk. She was very cute, he decided.

"Finn!" Logan yelled. Finn gave her one last once over, before turning back and following his friends.


A.N: Yes, a PDLD, I just can't get this idea out of my head, and I like what I'm going to do. I just know that this one is going to be long… very long lol. It's going to take place of Rory's summer, key moments of season four, Rory's summer in season five with some changes, and season five itself with lots of changes. It won't follow the show exactly, but I know that there will be moments that are in the show, others are my own little things.

I hope you all enjoyed!