(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.

Desperately, you search the crowd for Sam and see that he's making out with his short dance partner. Then, you look for your second possible savior, Cas, and see that he's still nowhere to be found. As a last resort, you look for Dean. Surprisingly, your eyes meet with his when you find him. His eyes focus on Jason, trying to assess the situation you were in. You give him a look that screams "HELP ME" and turn back to Jason before he notices your plan for escape.

Jason takes a sip of his drink, seemingly pondering something. He looks down at the counter, leaving you two in a terribly uncomfortable silence, despite the blaring dance music and chatter of the crowd.

You're just about to awkwardly excuse yourself when he finally turns to face you again. "Look, Des, I... I think about you a lot."

Fuck, here we go.

"I've really missed you since we broke up."

You mean since I dumped your miserable ass?

"And I really haven't been happy in a relationship since our breakup."

That's really weird, dude.

"So, if you're not seeing anyone currently..."

Don't. You. Dare. Say. It.

"Maybe we could - "

"Hey, Destiny!" A warm arm slips across your shoulders. You look up to see Dean's smiling face. He ignores your confused look and turns to Jason. "Who's this, babe?"

Babe?

That was new.

Jason stares up at Dean and shifts in his seat uncomfortably. He looks over at you and asks, "Uh, is this - "

"Her boyfriend? Yep, that's me. And you are?" Dean's eyebrow raises challengingly, and he shifts his weight so that he's leaning closer to you.

Jason chuckles nervously, nodding. "I'm just an old friend," He glances over at you and then back up at Dean. "I'll - I'll leave."

With that, Jason grabs his drink and scurries off, obviously intimidated by Dean's presence.

You let out a breath you didn't know you were holding and begin to laugh. "God, that was so weird," You shake your head and take another swig of your girly drink. Damn, you really needed to order something else. This wasn't cutting it. "Thanks, though, for saving me."

Dean removes his arm from your shoulders, taking Jason's seat beside you. "No problem. Guy seemed like a creep, and you looked like you couldn't get out of it. Funny, actually, because I've seen you take on horrible, terrifying monsters without a single flinch, but, throw in a scrawny, pushy boy and you absolutely freeze up." He laughs, enjoying poking fun at you but also seemingly searching for your explanation on why that is.

You chuckle and shrug, "Couldn't tell you why. I guess I'm just such a nice person and all."

Dean snorts. "You? Nice? I'd love to see that side of you."

You shove his shoulder roughly, which he just laughs at. "Bitch. I can be nice."

"Like I said, I'd love to see that." His lips turn up into a gorgeous smile, his eyes gleaming with joy.

You roll your eyes. You sink back into your thoughts, recounting the whole situation. "You know what, Dean?"

He hummed in response.

You bit your lip, feeling a little playful. "I think you saved me because you were jealous."

His amused expression quickly changed to confusion - borderline offended. "Me? Jealous? That's cute."

You gain a little confidence from the response you elicited from him, straightening your back in a more challenging way. "Mhm, don't deny it. You couldn't stand the sight of some boy throwing himself at me. You didn't want anyone else to have my affection," You hide your smirk behind your glass and, before you take a sip, add, "Isn't that right?"

"Yeah, okay," He scoffs, trying to grab at words but seems to be failing. Instead, he keeps pshing and scoffing, shaking his head.

Satisfied with how riled up you got him, you stand up, drink in hand. You lean close to his ear and whisper teasingly, "Don't worry, honey. Jealousy looks good on you."

When he looks up at you, you give him a little wink, and turn away before he can come up with some smartass rebuttal. As you walk away, you glance back to have one last look at the bumbling, lost-for-words Dean. You smile at the sight, feeling empowered, and call back, "You comin?"

You make your way over to Sam and Cas, who were chatting with the short girl clinging to Sam's arm. Cas looked horribly uncomfortable, seeing that he was being eye-fucked by every girl around him.

You knew that Dean wasn't too far behind you, and your mind raced with the possibility that he might want to confront you later to offer some bullshit explanation on why he was a stuttering mess. Maybe if you kept this little confidence charade up, things might take a very different turn tonight. You suddenly felt the urge to go to the bunker and find out.