Dean / Jealousy Looks Good on You

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(This imagine is for turtlelover1013 ! I'm sorry it took me so long, but hopefully you enjoyed it!)

You take a sip of your martini, surveying the lot of people in the crowded bar. Usually you would opt for something stronger, but you weren't in the mood to get shitfaced tonight. You were so, so tired after a long night of hunting. It was the boys who convinced you to go to this bar, and you were cursing their names mentally for bringing you here.

Speaking of the boys, where were they?

You scanned the crowd to look for their stupid, annoying-ass faces. Your eyes landed on Sam first - obviously, because he's a giant - and you see that he's dancing with a girl who is almost two feet shorter than him. You roll your eyes at the laughable height difference; she looked like his child rather than a love interest. Moving on, you try to spot Castiel, but give up after a while, assuming he's outside or taking care of some angel crap. Finally, your eyes land on Dean, who is shamelessly flirting with a young, very drunk blonde girl. She keeps touching his arm and laughing loudly in an equally shameless flirting fashion. They were perfect for each other - well, at least for a one night stand.

The hunt you had just finished took place in a town that was near your hometown, and you feared seeing anyone you knew. You had seen a few faces you recognized from your graduating class, but you made a beeline in the other direction in order to avoid them. You didn't think they would notice you, because you looked fairly different compared to your high school years, but you still dreaded the horribly painful small talk that would follow.

Enjoying the fruity taste of your more feminine drink, you try to relax and scroll through Instagram. You probably looked like an absolute loner to all the outgoing partiers, but you didn't really care.

Someone took a seat that was two down from you; you hardly noticed, immersed in your social media. It wasn't until they began ordering their drink of choice that you faintly recognized the man's voice.

You glanced over to him, and, to your absolute dread, the voice belonged to exactly who you thought it did: Jason, your ex from early college years. You two dated for almost a year (your first serious relationship) but you broke things off when you decided to uptake your new profession: hunting. He took it pretty hard, but, if you were being honest, you didn't care much for him.

You picked up your drink and tried to nonchalantly get up from your seat to leave, but he calls out, "Destiny?"

Freezing in place, you sigh quietly, put on a fake smile, and turn to him. "Hey!"

Jason's eyes were bright with happiness, and he laughed as he said, "Hey, I haven't seen you in a while!" He picks up his drink and scoots to the seat next to you. "What - " he chuckles again, "What have you been up to?"

You take a long sip of your martini, racking your brain for a viable profession. You put your drink down and say, "Uhm, I'm a personal trainer."

He scoffs, looking your body up and down. "Well, that explains your bangin' bod."

You laugh nervously, internally cringing at his choice of words. He always thought he was so "cool" and "hip", and you were quickly reminded that that was a main reason you dumped him.

He admires your face for a little too long, then shakes his head and says, "Sorry for staring, Des, but I just can't believe it's you!"

"Yeah, I can't believe it either.," you mutter. Putting on another fake smile, you continue, "I mean it's been like... three...?"

"Five years." He nods, his smile fading slightly.

"Yeah, five... five years..." your voice trails off, disappearing behind your glass and being silenced by a swig of your girly, currently unsatisfactory drink. You would need something stronger to get through this horrible conversation.

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