Disclaimer: The only thing I currently own is this wonderful CD by Josh Groban, not Gilmore Girls

A/N: Soooo, something else from me. This was originally going to be a one-shot but as of... five minutes ago, decided it was going to have about three chapter in it. The title is from Keith Urban... who I'm seeing in four days and can't wait!

Review: Please? It's really nice to have feedback, as long as it's not a flame, it helps the author more than you know. So help me out and review :-)

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Winter's weighing on your shoulders
It's hanging around a little too long
And I can see it in your eyes
You've taken on a load that's just too strong
Oh, but let me get down to the heart of the matter
Baby, if you want I can make it better now

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She didn't know what she was doing. She didn't even know why she agreed to this. She was out of her mind. Plain and simple. Her mother and herself had developed a reputation of being weird and quirky, but this was beyond reason. Why would she do such a thing? She was stupid. That was it, she was stupid. Rory Gilmore had agreed to go on a date with none other then Tristan Dugrey. She was loosing it. She couldn't fathom why she would do such a preposterous thing, it was out of reason.

They weren't buddy-buddy but nor were they at each others throat all the time. More along the lines of talking to each other in the halls. He toned it down – a lot. No more girls against her locker. Less of the "Mary" usage. They were on the tension walk that led them to being friends and out of no where... he asked her out. He was an ass. Who did he think he was?

Wait, if he was an ass for asking me out, what does that make me? she mused. Damn. She wanted nothing more than to pick up the phone and cancel but knew she couldn't, he was picking her up and forty-five minutes. If she canceled now, she would look like the worlds most horrible person. Besides, what harm could it do to go on one date with him? It wasn't like she would wither away.

She rested her forehead against the cool wood of her desk, not sure she would do this, she wasn't sure she was completely over Jess yet. It was Lorelai's and Lane voice that had probed her to agree to the date, hearing both of their voices telling her she wouldn't get over Jess by setting alone every night and doing her homework, or arranging her room for the hundredth time in a month. She couldn't do this.

Standing up, she walked to her wardrobe, gathering her clothes for the night, even if she didn't think she was ready, Tristan deserved better than that. He didn't deserve to have a thirty minute cancellation. No matter what state of mind she happened to be in. It wasn't like she despised him anymore... just weary of the of feelings he invoked in her. It was weird, it was like Jess was a transition boyfriend. She had liked Jess, she really had but the feeling of something missing always envelop her.

Never could she pin point what it was, it was just a slow, nagging feeling that never went away.

Lane had made the comment that Jess could have simply been a transition boyfriend, helping in preparing her for Tristan. So he could break the rose colored glass of what boyfriends were supposed to be that Dean had helped color in. And as she stood in front of her mirror, realization that Lane, just may have hit the nail on the head.

Tristan, he was gorgeous and could have any female he wanted, so what did he see in her? She didn't understand... there were girl ten times prettier than her and the fact he asked her out, boggled her. Sex, of course, had been her first assumption. She ruled that one out the moment she thought of all the females at school, he could have anyone of them any way he wanted them. Even Paris would have if given the chance.

He was mysterious. No one in the school could really tell you what they knew about him because no one new anything. Which brought his mysterious persona, which brought her to question what she thought she knew about Tristan Dugrey. Was he really the badass he portrayed to be or was he just as lost as everyone else in their school, searching for the place he too belonged?

Okay, so maybe the date wouldn't be so bad after all, Rory revised as she finished dressing for the date, heading towards the bathroom. Never, had she spent so much time thinking of someone she once claimed to hate.

Gosh, she hadn't been this confused since... well hell, there's a first for everything. She honestly could not remember when she had been so twisted with her thoughts that it gave her a headache. Geez, if just thinking about him had her mind muddled, what would the date itself be like?

Before she could think beyond that, the chime of the doorbell rang through the house. Taking a breathe, she stepped out of the bathroom, flicking the light off. She had placed her jacket and purse by the door beforehand so all she had to do was greet the person standing on the other side. As she swung the door open, the butterflies in her stomach pushed harder against her insides.

Okay, she wasn't expecting that or her jaw to drop and all her oxygen to suddenly leave her lungs. He stood on her porch, his jeans hanging on his hips in a way that made any female drool. The black sleeves of his shirt pushed to his elbows, his undershirt poking at the top. "Hi." she strutted, not used to being breathless around him.

"Hey. You ready?" If he noticed the ogling, he either ignored it or didn't catch it.

He had to conceal a groan as she opened the door, she looked so damn good. Her frilly brown skirt stopping just above her knees. With a white sleeveless V neck. Her hair was pulled into a pony-tail, he could barely tell she was wearing make-up, her skin looked the same just more... flawless. And her eyes were rimmed with brown eyeliner. She nodded. "Yeah..."

She stepped out, pulling the door shut behind her, not bothering to lock it. She smiled, seeing as he opened the passenger door before coming to the ring the bell. She slid into his warm leather seats, watching as he eased her door shut before making his way around the car. "Where are we going?" she asked as soon as he pulled his door shut.

He chuckled. "You just couldn't wait, could you?"

"You obviously haven't heard, Gilmore Girls' don't like surprises." she rattled off, trying to keep her frazzled nerves under control.

She saw him nodding from the corner of her eye, remaining silent. Confused was an understatement. She didn't know what to say with him, he didn't know anything from her town, moreover, she didn't think he'd care. With Dean, they chatted about happenings around town. With Jess it was books and music. With Tristan... she didn't know what to say. She, Rory Gilmore, always knew what to say.

That's two things she could add to the list of things of "first times ever to happen". She just didn't know him. And trying to start a conversation with someone you don't know was hard because you never knew if what you were going to say would upset them. You didn't want to lie either, if turned out to be more than one or two dates and they later brought it up, that was not the best idea either.

"You look good." Tristan said, giving her a side glance.

Rory bit her lip, curious as to why those words caused her insides to shiver in delight. Maybe it was his voice, the words ringing through her mind with his voice, she realized how deep, how smooth and rich it was. She was known as being odd, and in her eyes, liking his voice was another thing to add to the list.

With blush staining her cheeks, she looked over at him, once more giving him a once over. "Thanks. You don't look so bad yourself." she smiled to herself, satisfied when she saw the corners of his lips twitch upwards.

Maybe it wasn't going to be so bad after all.