DISCLAIMER: Gilmore Girls isn't mine. All characters belong to Amy Sherman-Palladino and the WB.

AN: This is a new story I'm working on. Before you start to read, you might be interested to read by blog entry (cocomango . blogspot . com/2005/11/new-fic . html) first. There are some thoughts, warnings, and explanations there about this story and why I'm writing it.

And of course, I'd like to thank my friend, M (Season4.5), for beta-ing this for me. This is just the prologue. Enjoy!

When You Least Expect It
01: Extra Chocolate Frosting

Tristan was bored.

Looking at his watch, he realized that it was time to leave since he had already stayed for over an hour. Placing his glass on the small table beside him, he stood in his full height and made his way towards the front door.

It was no surprise that several women, young and old, turned when he passed them. The moment he entered the room, women swarmed to him like bees to honey. Some gave him smiles while the others gave him seductive looks that didn't do anything for him. Two or three even ogled his backside.

He was almost home free when an elegant elderly woman walked in front of him. He was ready to ignore her and continue with his journey to freedom when the woman stopped and looked at him.

"Hello, dear," the woman said.

Tristan almost groaned. Please, let this be not grandma number five for the nights. But good breeding taught him to be respectful and polite. "Hello, ma'am. Good evening."

"I believe I've seen you before," the woman said, assessing him with her hawk-like gaze.

Of course she had. They were in the same society circle, weren't they? "I'm Tristan DuGrey, ma'am," he said, still pouring over the charm.

"Oh please call me Emily," she said, waving her hand. "So you're a Dugrey. Then you must be Janlen's grandson."

Tristan smiled genuinely at the mention of his grandfather's name. "Yes, ma'am."

"Emily?" said a booming voice behind them. Emily turned and faced the older gentleman. "Richard, this is Tristan DuGrey, Janlen's grandson."

"Ah! Really? A fine gentleman, your grandfather."

And so it started…again, the small talk, the polite conversation.

But sometimes, life throws a few good surprises, like extra chocolate frosting.

Rory had no plans of joining her grandparents that evening. However, Emily Gilmore could be persistent. Even though she was now more comfortable in these parties than before, there were times when she still felt out of place.

Spotting her grandparents, she also saw the young gentleman they were talking to. He looked familiar with his blond hair, blue eyes, and towering height. He reminded her of her ex-boyfriend, Logan. But this man had presence and he was more…captivating.

She watched them closely and saw the look on her grandmother's face. Warning bells started ringing. She just hoped that Emily wasn't selling her once again to this man. Her feet started to carry her to their direction and stopped as soon as she reached them.

Tristan saw her even as she was walking towards them. He felt as though he had met her before. She had brown hair and blue eyes, nothing spectacular about the way she looked, but hers was more of a quiet beauty.

Did he just say quiet beauty? That sounded gay.

"Ah, Rory," Richard greeted her granddaughter. "This is Tristan DuGrey, the grandson of a dear friend of mine."

Rory's eyes widened and her mouth formed an "o".

It was ironic how the people you thought you had forgotten and had locked away in your memory came back into your life and turned it upside down.

"Hello, Rory," Tristan greeted without mockery or teasing in his voice.

"Tristan, hi," she managed to say.

Richard cleared his throat. "Now why don't we leave you kids alone to catch up?" Emily nodded and let her husband lead her away.

Rory smiled. "I'm sorry about that."

Tristan tilted his head. "About what?"

"My grandparents. They just left us here to…catch up."

Tristan let out a chuckle. "Yeah," he said. "They weren't being subtle, were they?"

Rory laughed and shook her head. Finally, their laughter died down, and she suddenly felt shy.

A waiter with a tray stopped and offered them caviar and hors d' oeuvres. Tristan's stomach grumbled but refused to eat any of the fare. "So, are you having a good time?" he asked.

"Yeah…"

Tristan's pearly whites appeared. "Really?"

Smiling sheepishly, Rory said, "No, not really."

There are times when friends can make you feel awkward, and semi-strangers can make you feel at ease.

"I was just about to leave and I'm really hungry. Would you like to join me to grab a burger or something?" Simple. Direct. To the point. No pressure.

At the mention of real food, Rory's eyes lit up. "Does it go with fries?"

"And milkshake."

"I'm in."

The night may not be so boring after all.

TBC...