A/N: I wrote this about a year ago in the middle of history class. I just found it in my old notebook. A friend had requested that I write Dean flirting with Amy and this is what happened. Apologies for any lack of goodness, but please do review!
Dean slid onto the empty barstool and cast an appreciative glance at the long legs and short skirt of the redhead on the next seat over. "Two beers," he asked the barkeep, and gestured for one to be passed to the chick.
She turned to face him and raised one delicate. skeptical eyebrow. Clearly used to dismissing guys at bars. But she didn't know she was up against a mast. Dean smiled invitingly and took a swig; she shrugged and matched him drop for drop. "Thanks." Her accent was Scottish: sexy.
"My pleasure," he replied smoothly. "I'm Dean."
"Amy," said the girl, taking another sip of her beer. "Amy Pond." There was a wicked gleam in her eyes that Dean definitely liked.
"You come here often?" he asked casually. Cheesiest pick-up line in the world, but they actually did need to talk to a local. Three mysterious disappearances in a week practically screamed "supernatural beastie," but neither the city police nor Bobby could turn up anything specific.
Amy smiled like she knew a secret. "Just passing through, sorry. I'm traveling with a friend."
Damn, and the way she said "friend" suggested that Dean wasn't going to get lucky tonight on that front either. Ah hell, he was stubborn. He shot her another lopsided smile. "Glad I caught you tonight, then."
She returned his smirk with a laugh and a toss of her head, warm orange hair glinting in the dim fluorescent lights. "Lucky me," she purred.
Of course Sammy chose that moment to run up to the bar. "Dean," he cried urgently, waving some old book like a total dweeb. "Dean, I think I found it. In this Ancient Chronicle of Blah Blah blah..."
Dean rolled his eyes at the chick, who smirked knowingly. But before he could deliver some suave, witty remark to make his little brother shut up and go away, another guy pushed his way through the crowd and grabbed Amy's elbow.
"Amy, good, there you are," said the guy, panting slightly. He looked, if possible, even dorkier than Sam, with red suspenders, a lopsided bowtie, and a floppy haircut that reminded Dean of Sammy circa age eight. Not that Dean took note of the haircut, because that wasn't something guys paid attention to.
Floppy Hair was rambling something about the cemetery at the end of town, and Sam was looking vaguely interested, but Dean interrupted the flow of babble. "Hey, you know this guy?" he asked Amy guardedly. Though judging by the way her eyes had lit up, this was the "friend." Damn it.
Floppy Hair seemed to notice the Winchesters then, and his eyes lit up too. "Dean!" he exclaimed delightedly, grabbing the hunter's shoulder and air-kissing him on both cheeks. "And Sam!" Sammy got the same weirdo greeting. Dean hoped his own face didn't look that totally befuddled.
The stranger stepped back and looked around expectantly. "Where's Castiel?"
"What's a 'Castiel'?" demanded Dean, surprise transitioning smoothly to anger. "And who the hell are you?"
Floppy Hair checked his wristwatch. "Oh, it's only 2007," he said disappointedly. "Sorry, we haven't met yet. From your point of view." He peered critically at the brothers faces. "And you still think it's all magic, don't you."
Dean glanced over at Sam, expecting to share a "what a nut" glance. Instead, Sammy was staring at the man like he was a great song whose lyrics Sam was trying desperately to remember.
"We'd better go," continued Floppy Hair, oblivious or deliberately ignorant of Dean's skepticism. "Don't worry, we've got this one. Try Minnesota; I think there's a Thing there." He plucked impatiently at Amy's sleeve. "Come along, Pond!"
She swigged the last of her beer and hopped off the stool, casting an unapologetic grin back at Dean as she followed her friend to the door. "See you, boys. Thanks for the drink!"
The Winchesters stared after them as the rest of the bar continued its path to inebriation.
"What––" Dean finally began, but he was interrupted once more by Floppy Hair poking his head back in through a side door Dean hadn't even noticed before and calling across the bar, "Tell Castiel I'm going to want that trench coat back eventually!" The door closed again with a soft snap, and he was gone.
"––the hell just was that?" Dean finished, completely nonplussed.
"I'm not sure." Sam blinked in confusion, rubbing his head. "But I swear that guy seemed familiar. Like I'd seen him in a dream or something, you know?" He frowned. "And who is 'Castiel'?"
And that boded well, with the sort of dreams Sam got. "Probably nobody important," grumbled Dean. "Or someone just as weird."
"So now what?" asked Sammy.
"Now what?" answered Dean.
"So are we going to the cemetery, or to Minnesota?"
