Disclaimer: I don't own any part of Gilmore Girls or its characters – the only thing I came up with was the story line.

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Chapter 2: It's A Small World After All

"What are you doing here?"

Hearing this, Dean smiled with amusement. Never before had he seen the normally unflappable Jess so flabbergasted, and to be honest, he found it kind of funny. But he didn't say anything, choosing instead to turn his attention to his old friend behind the counter. "Hey, Dave. I'll have the usual."

"Coming right up," Dave nodded, moving away to grab a mug, leaving Jess to stare at Dean.

"Since when do you come in here?" Jess asked, his voice suspicious as he looked the tall young man up and down, summing him up, trying to figure out his reasons for being there.

Dean shrugged casually as he accepted the tall, frothy mug of beer Dave slid his way. "I come in here all the time. Don't I, Dave?"

"I can vouch for that." Shifting his gaze from Jess to Dean, Dave's eyebrows quirked. "You never told me you two knew each other."

"You never asked," Dean smiled, glancing at Jess.

"And I never thought I'd see you again," Jess frowned, popping another pretzel in his mouth. He pushed the opened bag toward Dean, who accepted it with a nod. "So back to my question. What're you doing here?"

"The same reason you are," Dean replied simply, and Jess smiled, knowing he didn't need any further explanations.

Jess grinned and turned to Dave. "Remember the guy I was talking about a minute ago – the guy with all the issues?" When Dave nodded, Jess couldn't help smirking. "Well, here he is, in the flesh. How's that for irony, huh?"

A look of perplexity crossed Dean's face. "Dare I even ask why you two were talking about me?"

"Oh, sure," Dave laughed. "Jess and I were having a little man-to-man talk, you know, the usual stuff – women troubles, one in particular…"

"Ah, of course," Dean smiled meaningfully. "Rory." Sighing, he reached for his beer again.

"Oh, wait a second," Dave grinned. "Don't tell me – you've got the blues too, huh?"

Dean nodded, managing to look embarrassed, doleful and resigned all at once. Seeing the younger man's reaction, Dave smiled.

"Man, I have got to meet this girl," the barman shook his head. "She must be one helluva woman to have affected you both like this."

"Oh yeah, she is," Jess said, sharing a conspiring grin with Dean.

"She is," Dean echoed, his voice wistful and affectionate as a half-buried memory of a certain blue-eyed brunette flickered across his mind. He sighed. "She really is."

Dave smiled again. "So, what's your story, Dean?"

"My story?" Dean glanced up.

"Yeah," Jess said, tilting his head as he studied his beer. "I've already told Dave all about how we hated each other's guts back when we were sixteen, so now's your chance to tell him your side of the story."

"Hell, why not?" Dean exhaled. "Let's see…" He paused for a moment as he struggled to remember. "I moved to Stars Hollow from Chicago when I was sixteen, and I met Rory in high school. That is, before she got into that snooty rich school."

"Chilton Prep," Jess offered, for Dave's benefit.

"That's right," Dean nodded absently. "Anyway, we started going out."

Dave looked at Dean expectantly. "And?"

"We dated, we had our ups and downs," Dean continued before shooting a knowing look in Jess's direction. "And I had a tough time beating down the competition."

Jess grinned. "Oh, yeah. I seem to recall a certain incident at this basket-buying fundraiser a couple of years ago…"

"Of course," Dean chuckled. "That was quite a day, huh?"

"Care to share?" Dave asked. "I'm a little lost here."

"Well," Jess said, resting his elbows on the counter. "Stars Hollow is one of those small little towns with all sorts of weird traditions, and the Bid on a Basket Fundraiser is no exception."

"Yeah," Dean nodded, grinning. "The women in the town are supposed to put together these food baskets, and later on, the men are supposed to bid on them. Whoever with the highest offer wins."

"And when Rory's basket came on, I decided to give Dean a run for his money," Jess continued, pausing to slap Dean on the shoulder.

"So who got the basket?" Dave inquired.

"Jess did," Dean smirked. "For the grand total of ninety dollars."

"Ninety dollars," Jess confirmed, unable to keep the grin from his face. "I paid ninety dollars for some leftovers."

Dave guffawed. "You're kidding me."

"I'm not," Jess assured the older man, his eyes twinkling. "But the whole thing was kind of funny, actually." He turned to Dean. "You should've seen your face, man. Fourteen shades of purple."

"What can I say?" Dean shrugged philosophically. "I was sixteen, and madly in love with Rory Gilmore." He laughed quietly. "Plus, I hated you with a passion. You home wrecker." But there was no real malice in his words – any hatred he had once borne toward the other man had faded away with time, and now he looked upon those days only with fondness and slight regret.

"I'm sorry I gave you such a hard time, dude," Jess said, his face growing serious.

"No problem," Dean smiled slightly. "We were kids."

A wry grin twisted Jess's lips. "Yeah, messed up ones at that."

"Hey, speak for yourself," Dean teased, punching Jess's arm lightly. "How about another round, Dave?"

"Sure thing," Dave nodded distractedly, refilling both mugs. "So tell me, what happened to Rory Gilmore?"

Before the other two could answer though, a deep voice spoke up from behind them. "Oh, I can answer that one for you." Instantly, the three men turned to look at the stranger who had just entered the bar. Jess looked on with confusion as recognition flashed in Dean's eyes.

It was Dean who eventually broke the momentary silence. "Oh, you have got to be kidding me."

*

To Be Continued…