TITLE: "What's Up Lonely?"

SUMMARY: Rory never got back together with Dean after the first break-up. She doesn't want to admit it, but she is lonely. Can a certain Chiltonite raise her spirits? Title from a Kelly Clarkson song.

DISCLAIMER: I do not own anything involved with Gilmore Girls or the song "What's Up Lonely?" by Kelly Clarkson. I am just borrowing them for a little while.

Hey guys, I'm back! I'm on Winter Break and I can't help myself! I know this has been done a million times before, but please try it! Who can't get enough TRORY anyway? I'm trying another chaptered story, so I hope it goes well! Now, on with the story!

It had been three months since Rory saw Dean last. She had finally admitted to herself that they were really over and took off her bracelet and placed it in the 'Dean box.' No matter how much it hurt, she knew it was right. She cared for him, but she knew that she didn't love him. After all, now she could focus all of her attention on getting into Harvard. At least that's what she kept telling herself.

Tristan DuGrey was extremely bored. The girl in front of him was droning on and on about something or another, but he had stopped listening after "hello." Why did all of the girls at school have to be mindless idiots? Well, not all of them. There was of course, Paris, but no way would he go down that road again. And then there was Rory Gilmore. His Mary. He had tried and failed on several occasions with Rory, but he was still completely infatuated with her. He had heard from Paris that she had broken up with the Bagboy. He would love to have a word with him for making Rory sulk around the halls of Chilton for the last few months. It wasn't right to see her beautiful blue eyes so lifeless. "Don't you think so Tris?"

Startled from his thoughts, Tristan said, "Oh yeah, absolutely." I have no idea what this airhead is talking about, he thought.

Completely oblivious to the fact that she was being ignored, the girl continued on. "I know! It's going to be the social event of the year. So, you'll pick me up at 7?"

Seeing Rory walking towards her locker, Tristan said, "Um, yeah, sure. I'll see you later."

Obviously pleased with herself, the girl skipped off to talk to her nearby friends. Rory was being closely followed by Paris, and Tristan was looking forward to a show. "Come on Rory. My mom says I have to go and I really need someone who isn't completely mindless to talk to."

"Oh, well, when you put it that way Paris…" Rory said as she started putting away her books for the day.

Rolling her eyes, Paris said, "So I can pick you up at your house? Maybe even borrow an outfit?"

"I don't know Paris. That didn't work out so well last time."

"That was when you were setting me up with that jerk Tristan. You're not planning on doing that again, are you?"

Tristan became very interested, and slowly crept his way closer to the two girls.

"No, I'm not. Okay, I'll go with you, but as soon as the clock hits 10:00, we're out of there, right?"

"Like I'd stay any longer than the required time by my mother. See you later Gilmore."

Paris walked off, leaving Rory muttering to herself. "I can't believe I just got roped into that. I better bring a good book."

"You know Mary, parties are supposed to be fun. No need for books."

Annoyed, Rory said, "Oh yeah, because the last party I attended worked out so well for the both of us. You got dumped and I made a stupid decision."

Pretending to not be hurt by the comment, Tristan said, "I don't know what you're talking about Mary. I thought that party was one of my best."

"Yeah, I'm sure YOU did. I have to catch my bus, so if you would excuse me."

Following her, Tristan said, "You know, I could-"

Not turning around, Rory replied, "No thanks."

Rory had made it to the door, and Tristan yelled, "You didn't even know what I was going to say!"

"Yes, I did!" With that, Rory left the building and headed towards her bus. Tristan just smirked and shook his head in amusement. The prospect of tonight's party just got a lot better.

Lorelai was drinking her coffee at the kitchen table when she took one look at Rory and started laughing.

"What?" Rory asked, looking down at herself.

"Oh, nothing. I just get the Mary reference is all." Lorelai said.

Sighing, Rory said, "I really wish I never told you that. What's wrong with this outfit?"

"Nothing if you're going to church with Mrs. Kim, but a party? Come on Ror, I think we can find something better than that."

Lorelai grabbed Rory's arm and dragged her back into her room. Rummaging through the closet, she came out a minute later with a denim miniskirt and plain black tank top. "See, simple but definitely not plain. Now put it on!"

"Mom, I appreciate the help and all, but I really don't want to get dressed up for a night of sitting on some stranger's couch and reading."

Smiling mischievously, Lorelai said, "Oh, about that, I lost your big purse last week. I guess there won't be any room for a book."

"Oh, don't worry, I can carry it." Rory said, reluctantly pulling on the clothes her mom had handed her.

"Hun, will you please just try to have fun tonight? You've been so down lately, you could use a little teenage partying."

"If I promise not to bring a book, you promise to lay off me?" Rory asked.

"Of course. Now if I could only get you to promise to dance-"

Lorelai was interrupted by the doorbell. She sighed and went to answer the door, returning with Paris.

"Okay, now what should I wear?" Paris asked.

"I think you better let my mom take this one. If it were up to me, we wouldn't be going to this stupid party." Rory said, while taking her hair down.

"Paris, I have just the thing for you! Hang on one second!" Lorelai ran upstairs and returned a minute later with a black skirt and see-through top with a white camisole under it.

Paris eyed if for a second, and said, "I guess that will work. I'll be back." She headed towards the bathroom to change.

Lorelai grabbed Rory's hand and sat her in front of the mirror. Skillfully, she applied light eyeliner and mascara to Rory's face. "There, perfect."

"Okay, mom. That's enough. I think I'm good to go."

Paris returned in Lorelai's outfit looking shy and uncomfortable. Noticing this, Lorelai said, "Oh, Paris, you look wonderful."

Timidly, Paris said, "Thanks." Pulling on her jacket she turned to Rory and said, "We should probably get going. We'll be back at 10:45 at the latest, trust me."

Walking them out, Lorelai said, "And if you guys get really crazy you can come back at midnight."

"Yeah, yeah, I get the hint mom. I'll see you later." Rory hugged Lorelai goodbye and went off to Paris' BMW.

They pulled into a Chilton student's mansion in Hartford about 45 minutes later. "Let's get this over with." Rory said, following Paris to the door.

As soon as they walked in, Rory was met with the smell of alcohol and smoke. She immediately wished that she hadn't been talked out of taking her book with her. Once they had found the only non-alcoholic drinks in the place, Rory and Paris were at a loss of what to do. So, they stood by the refreshment table talking. Tristan, who had just arrived with Lauren, the annoying girl from earlier, took notice of Rory right away. He had heard her say she was coming, but never actually expected her to show up. She was standing talking to Paris, looking incredibly bored, but also incredibly beautiful. Her skirt was just the right length and her simple top was more flattering than any of the flashy outfits that the girls around him were poured into. Excusing himself to Lauren, he headed over to the drinks table.

"My, my, my, if it isn't Mary and Paris. At a party, who would have thought?"

Shooting him an annoyed look, Paris said, "Oh get lost, DuGrey. Don't you have some slut to tend to?"

"Oh, she'll be there when I get back, trust me." Tristan took a swig of his newly acquired beer, and gave Rory an appreciative, but subtle, glance over.

"She's a lucky girl, that one. How long will this one last?" Paris asked, while Rory remained standing silently giving Tristan a look-over herself. She had to admit, Tristan in jeans and a t-shirt was definitely flattering. Willing the thoughts out of her mind, she decided to concentrate on the punch that was in her hand.

"Jealous, Paris? Cause, you know I can always make room for the two of you."

"Eh, no thanks. I wouldn't want to catch anything." Paris said disgustedly. She had obviously gotten over her crush, Tristan thought. Now, Rory on the other hand was being awfully quiet.

"Mary, you are looking awfully good tonight." Tristan said, turning his complete focus to Rory.

Uncomfortable by his attention, Rory said, "Thanks. I think I'm going to go find a bathroom."

Before he could say another word, Rory was already on her way. Glancing around, bored, Tristan's eyes landed on the punch bowl and the cup that Rory had just handed Paris. "You do know that is alcoholic, right?"

"I do, but Rory doesn't. I thought I would just let her have one, let her loosen up a little." Paris said guiltily.

"Paris, I don't know if that is such a good idea." Tristan said.

"Oh, relax DuGrey, it won't kill her."

Tristan just shook his head and walked away in search of his friends. Or, actually in search of Rory. He had just decided that it was his job to watch out for Rory tonight. He knew that she wasn't a drinker, but he also didn't want to embarrass her by telling her the truth. He would just make sure she didn't overdue it. Now he actually had an excuse to look at her all night, something he would never say no to.

Hope you guys enjoyed it! Please, please review because I need feedback to know how to continue! Thanks for reading and I should update soon if it turns out anyone likes it!