10/13/05—just did a major rewrite. Lots of changes so if you read it before, check it out.

Also, remember, this story is AU. Tristan and Rory did go to Chilton together, but he never called her Mary and nothing happened between them unless otherwise stated. So I'd say in this story, Tristan went to Chilton with Rory for a couple of months and during sophomore year, the break-in to the safe happened, sending him to military school.

Can't Bet with Love

Part 1: a bet is made.

Tristan Dugray sat in the coffee shop on Yale's campus with his three closest friends: Erik Hansen, Charlie Richards, and Michael Pratt. He normally wouldn't have been able to get into Yale if it hadn't been for his parents, who pulled a few strings. Erik and Charlie were the same. Guys with rich parents that normally wouldn't be able to get into an ivy-league school like Yale. Michael, on the other hand, had received almost a full scholarship to Yale, as his family wasn't nearly as well off as the others.

It wasn't that Tristan couldn't get into Yale, though. If he had tried, he could have earned a scholarship just like Erik, but instead he'd spent most of his high school years goofing off, spending more time with his friends than with his schoolwork. Well, it was more like spending all of his time with his friends and leaving no time for schoolwork. And that was exactly how he planned to go through college.

"Whoa, babe standing at the cash register," Erik said.

He was always point out some girl that he found hot, wherever they went. Erik never went after the girls since he had a serious girlfriend, but he always said that didn't

Tristan didn't understand how Erik's girlfriend, Mallory King, could stand the fact that Erik checked out other girls. All of his ex-girlfriends would get really mad if he even as so much looked at a girl—even if it was to order some coffee, dinner, or something like that. Erik said Mallory wasn't worried because she knew that Erik really loved her—which Tristan knew that he did. Whenever Erik was with Mallory, he focused on her and only her; not even bothering to look at any other girls. He even talked about Mallory all the time and he, Charlie, and Michael always teased him that he was whipped.

"I could get her," Charlie said.

"Sure you could," Tristan said, rolling his eyes. He knew that Charlie was all talk, no action. Charlie always said that he could get any girl, but he never did anything about it, whereas Tristan would say it and then would actually get the girl. He liked to think that he was both talk and action.

"I'd like to see you try and get her," Charlie said. "You think that you're the gift to all woman. Like every single woman would come to you when you snap your fingers."

Tristan rolled his eyes once again, shaking his head. "I'm not the Fonzi, I don't have to snap my fingers. They just come to me."

"Man, do you seriously think that you could get any girl?" Michael asked, leaning forward in his seat.

"I bet that you can't name one girl that I couldn't get," Tristan said with a smug smile. He knew that he was good looking and that many girls liked him.

Michael glanced at the door, his eyes following the pair that just walked in.

Tristan followed his line of sight, focused on two girls. They looked familiar, particularly the shorter of the two. She had long, light brownish blonde hair that reached about halfway down her back. Her eyes were dark; her mouth was set in an even line. Her name was on the tip of his tongue—she'd gone to school with him prior to Yale.

The other girl stood at about 5'7" with chocolate brown hair, falling into layers, just a bit shorter than her friend's. Her eyes were vivid blue, ones that he could see even across the room; a smile crossed her lips, a cleft appearing in her chin; her cheeks painted with a light dusty rose blush. While she looked familiar, he couldn't place her as well as he could place the other—and she didn't look like someone that he'd be able to forget all that easily.

"Rory Gilmore," Michael announced, noticing that Tristan was looking at her as well. "She's in my English class and I'll admit this, I tried to ask her out, numerous times might I add, but she declined every single offer."

Tristan looked up at the two girls again. Rory Gilmore. He repeated the name over and over in his head before he finally recognized that name. She had gone to Chilton with him. That was until he had gone to military school for trying to break into a safe that belonged to one of his friend's parents, along with that friend and another friend. After some consideration, he determined the other girl to be Paris Gellar, a girl that he had known since kindergarten.

"I could get her," Tristan said, understanding the challenge in Michael's voice. Although Michael was a bit of a brain, Tristan had to admit that he was up there in the look departments and his though the number of dates he had paled in comparison to Tristan's, his line of girls wasn't short.

"I'd like to see you try," Michael smirked. "The girl is practically an angel; I hear she's a virgin."

"I still know that I could get her," Tristan said. It wasn't like he'd never dated and "broken" other virgins before. "Not only to go out with but also…" he trailed off. His friends knew what he was talking about so there was no need to finish his sentence.

"I don't think Tristan could get Rory Gilmore," Charlie said, although he'd never heard of her before today. "She seems like a girl who'd want a long-lasting relationship." Charlie stressed the word "girl" with a smirk. "And a long-term relationship to Tristan is having sex with a girl more than once."

"I bet you two thousand dollars that in one month's time, you couldn't get Rory Gilmore to sleep with you," Erik said.

Tristan smiled. "Easy," he said. "We can even shorten the bet if you'd like."

"Three weeks sound good to you?" Erik offered up.

In just three weeks, he would have an easy a thousand dollars. There was never a girl that said no to Tristan Dugray. He doubted that Rory Gilmore would be the first. He looked at Charlie and Michael. "Want to add some money to that?" he asked.

"I'll add a thousand," Charlie said without hesitation. It wasn't as much as Erik's offer, but he knew that Charlie was a little more cautious in losing his money since his parents weren't quite as loose with their money as Erik's and Tristan's parents were.

Michael was more hesitant. Tristan knew it was not because of money, though Michael didn't have much to offer up, but because he didn't know for sure whether or not Rory Gilmore could and would resist Tristan's so-called charms. He smiled, finally decided to go with his first intuition. "A thousand dollars," he said.

Tristan knew that was a stretch for Michael to offer up so he must've been pretty sure with his option.

"It's a deal," Tristan said. "And if Rory"—he stopped for a second and laughed—"if Rory doesn't, I'll owe you guys the four thousand."

"Each," Charlie added.

Tristan shook his head. There would be now way that he would be spending twelve thousand—not that he would have to.

"If you're so confident that you're going to win, why does it matter? Unless, you don't have total confidence…" Erik trailed off with a smirk, knowing how to get to Tristan.

"Yeah," Michael said. "Plus, if you lose a bet, you should have to do more than just pay us. There should be something extra…"

Tristan gave them a cocky grin. "Fine, twelve thou."

"You at least have to do something more than that if you lose," Charlie said. "Michael's right. The stakes aren't high enough. You are the betee here."

"I'm the what?" Tristan asked.

"The betee," Charlie repeated. "We're the beters and your the betee. So we are betting you four thousand dollars that we'll give to you if you win. But if you lose you have to…"

"Give us the twelve thou…" Erik continued.

"Run around in tighty whities with a monkey strapped to it?" Charlie suggested. When he earned questioning glances from the others, he offered a shrug. "What? Graduation isn't for another two years so we can't go She's All That."

"That's lame," Erik commented.

"You have to remain celibate for life," Michael offered up.

"That's just too cruel," Erik said with a laugh. "How about at least a month? If we're sticking with movie teams, we can go 40 Days and 40 Nights on him."

Michael shook his head. "Now this is just said. First, Charlie has seen She's All That and now you've seen 40 Days and 40 Nights."

Erik smirked. "What can I say? That Josh Hartnett is a hot-tay. And I don't blame Charlie. Freddie Prince Jr. and Paul Walker? Can we say a two-for-one deal?"

"Wow…watch chick flicks much?" Tristan asked.

"I do have a girlfriend and three sisters, thank you very much," Erik responded.

"Still…" Michael just shook his head, trailing off. "Is it a bet?" he asked.

Tristan nodded and reached out and shook hands with each of his friends.

As the conversation was brought back to the fact Erik knew chick flicks, he leaned back against the booth, his hands behind his head. This would be easy. All he had to do was make his first move.

---

Rory Gilmore sipped her coffee as she sat across from Paris Gellar, who had surprisingly become her best friend—at Yale and almost otherwise. Her mother still remained her best friend, as well, but, though Stars Hollow was nearby, Rory needed someone to talk to when she while she was at Yale within walking distance (in this case, she just turned to the next bed). It kept the phone bills down from Rory having to call her mother more than at least twice a day.

"Has Dean called yet today?" Paris asked.

Rory was still going out with Dean, her longtime sweetheart. He called at least once a day; he was still in Stars Hollow. It was hard, but they had kept their relationship together even though it had become a long-distance one. Plus, a 70-minute drive between Stars Hollow and Yale wasn't too bad.

Rory nodded. "He told me that he wants to talk to me about something really important and that it can't be done over the phone," she said with a shrug. "He's coming up tomorrow."

"He wants to talk to you about something important, huh?" Paris questioned. "You guys have been going out for four years now, think he may propose?"

Rory face lit up at the suggestion. Why hadn't she thought of that before? Of course he would propose. They had been together for around four years now, like Paris had said. Rory had contemplated breaking up with Dean the summer before their senior year due to feelings she'd developed for Luke's nephew, Jess Mariano, but after Rory's summer spent in Washington, Jess had hooked up with another girl, giving Rory a hard time when she came back. So, she gave Dean another chance, which she was happy that she had done so, as Jess had disappeared sometime during their senior year. They were, however, on okay terms when he left, as he'd long since broken up with his summer-girl, Shane.

"He's coming up tomorrow, you said?" Paris asked, interrupting Rory's thoughts.

"He is driving up here to see me tomorrow about mid-afternoon and then will drive back later at night," Rory said. She sucked out the last bit of her coffee through the straw and then started to get up. "I'm going to get another coffee to go and then why don't we leave? I feel like dancing right now."

"I'm not going to one of those clubs or a party," Paris said as she and Rory headed over to the counter. "My mom isn't her to force me to go to one."

Paris had changed since high school, but not with the social aspect. No parties for her.

"No, she's not here," Rory said, grinning. "But I'm here to force you to go to one. Please? As a celebration for my soon-to-be engagement with Dean?"

"Why can't we just go to dinner somewhere with a few friends and call that a celebration?" Paris asked.

"Because I want to dance, not eat," Rory said. She wasn't really a party person either; she had only been to a few dances in her life. But right now she was in the mood to go to one.

Paris didn't answer because Rory had reached the front of the line. Rory ordered her coffee and then once she had received it, she and Paris left.

"Please, please, please?" Rory begged as they walked across the quad, back to their dorm.

"I have a test coming up in physics next week," Paris said. "I really need to study for it."

"I promise you that I'll help you study for that test starting tomorrow and everyday up until you take the test if you go to that party with me," Rory begged. "Please, please, please?"

"Fine, I'll go with you," Paris relented.

"Yay!" Rory exclaimed. She started skipping around.

"Rory, stop it!" Paris exclaimed, slightly embarrassed at her friend's antics.

"Sorry, I'm just so…excited! My best friend and I are going to go to a party and I'm going to get married!" Rory exclaimed. "Nothing in the world could go wrong."

"I just felt a drip-drop," Paris said, looking up into the sky that was filled with gray clouds, nothing clear in sight. "Rory, whenever someone says that nothing could go wrong, something always goes wrong."

It started to pour; the rain wasn't gentle and it hurt Rory's arms, as she was only wearing a light t-shirt, but she danced around in it, holding her arms above her head. Though she was getting drenched, nothing was going to get her down today.

Note: I don't own the movies that were mentioned…or anything else that may have slipped my mind at the moment. Also, I've never seen 40 Days 40 Nights so I don't know if it was quite a chick flick or not…but good enough for this chapter.