Wrong End of the Deal

Untitled Part 1

It had been a long day at work. One of those days that made you wonder why you'd picked your field to go into; didn't your mom tell you that it meant nothing but long hours and low pay? Sighing, you finished your cocktail and nodded at the bartender.

"Let me get another one, Jon." Thank God it's Friday.

You'd been coming to this bar for long enough that Jon knew you, and he shot you a sympathetic look as he mixed your drink. "Another bad one, Y/N?"

You nodded. "Yeah. Why did I think this job was a good idea?" you asked rhetorically.

"Because it must pay really well, darlin'," Jon replied, placing the fresh drink in front of you and removing the empty glass. Before you could respond and tell him that, in fact, lobbying against Big Pharma paid next to nothing, a rough male voice called out for beer at the other end of the bar and Jon moved away to fulfill the order.

You exhaled and scrubbed your hands over your face, remembering just in time that you were wearing makeup and managing not to make yourself look like a raccoon. This is the last drink, you told yourself. Any more and I'll have to Uber home.

Lost in your thoughts, you didn't notice that the man at the far end of the bar was staring at you, recognition slowly spreading across his face. It was a complete shock when he called out, "Y/N! Is that you? What are you doing here?"

You jumped, almost falling off your barstool. Whoops. Maybe it's Uber after all. You squinted in the direction of the voice, then almost fell off the barstool again when you recognized its source. "Dean? Dean Winchester?"

Your ex got up and headed towards you, flashing that stunningly attractive smile that had made you fall into his arms years ago. You felt your knees go weak, then sternly reminded yourself that you had broken the relationship off for a reason; unfortunately, with Dean getting steadily closer, it was hard to remember what that reason was...

You jerked yourself back to the present as Dean slid onto the stool on your right. "How're you doin', Y/N?"

"I'm – I'm good," you managed to get out. "What about you?" Frowning, you scanned the bar for Dean's 6'4" monster-hunting partner-in-crime. "Where's Sam?"

A shadow seemed to cross Dean's face, but it was immediately covered by a blinding grin. "We've decided we need to split up for a while, you know? There is a such thing as too much brother-ness." He frowned. "Is that a word?"

"No, no it's not," you replied absently. Since when was there a such thing as too much brotherly togetherness for the Winchesters? When you and Dean had been together, you'd seen Sam almost as much as your boyfriend, since they never went anywhere without the other.

"Well, you would know," Dean said cheerfully. "You've always been the smart one."

The two of you spent the next thirty minutes talking about some of the changes in your life before the conversation veered around to Dean. "Well, like I said, Sammy and me are takin' some time apart," he said, fiddling with his beer bottle. "I got – cursed, I guess, last year, and I did some things he didn't like, and he did some things I didn't like, and we decided we should split for a while, y'know?"

"Yeah," you said, spinning your empty glass around on the bar – was this drink number four? Five? "Sometimes it's the people we love the most that we need space from. I know with my fiance -"

"Wait," Dean interrupted. "You're engaged?!"

You blushed and held up your left hand, displaying the modest ring. "I met him a couple of years ago, and we just kinda clicked, you know? We're getting married in three weeks and two days." You blushed harder. "Not like I'm counting down or anything."