The Other Side of the Bar
Summary: Bartender!Dean AU where he has a bet with you each night to see who can keep a straight face the longest. In Sam’s words, “This was the weirdest damn flirting he’d ever seen.”
Word Count: 2351
A/N: I have this headcanon that if it wasn’t for Azazel and the hunting life, Dean would be the happiest guy out there. He would just be loving life and laughing around and basically be a force of nature that always gets what he wants. He would be unstoppable and would be so damn happy. So that’s the version of Dean that I imagined for this AU.
“Sam, my man!” Terrance bellowed when Sam walked into the bar. Upon seeing his old friend, Sam broke into a smile and gripped his hand, pulling him in for hug. “Our boy Dean didn’t tell me you were in town.”
“Well, finals are finally over and Dean’s been after me about checking out his new bar since he opened it.” Sam glanced around the dimly lit room and couldn’t help but feel impressed. “So I thought I’d surprise him.”
For someone who hadn’t set foot in a college classroom, Dean was actually a pretty good businessman. This was the third bar that he’d opened in Eastern Kansas, and every bar that he owned was doing ridiculously well. When Dean asked Sam to take a look at his finances and make sure that everything looked good, Sam started rethinking his own life plan. If Dean was making that much per bar, then what in the world was Sam thinking, digging himself deeper into debt to get a law degree?
Speaking of Dean, Sam glanced around the packed room in search of his sandy-haired brother. As usual, he was behind the bar talking to a chick. But he wasn’t smiling or joking around like he usually did in the company of any living, breathing female.
“What the hell?” Sam asked, drawing Terrance’s attention. “He’s having an actual conversation with her instead of just flirting?”