Supernatural Imagines for The Soul

Awkward Moments

You sat at a secluded booth at the bar while waiting for your best friend. The two of you were going to have a girl's night out after you had gone through a horrible breakup. The only good thing that came out of the breakup is that you got to walk away after kicking your ex in the balls. Afterwhich you had called up your best friend and told her you needed a distraction, and she suggested having a girl's night out at your favourite bar. You waited for about half an hour so you decied to text her.

"Hey [Friend's Name], are you coming soon? I've been waiting for 30 mins now."

The reply came sooner than you expected.

"Yeah! I'm walking over now."  That gave you the reassurance you needed and waited for a while more. Soon enough someone walked over to your booth, and since the bar was pretty dimly lit, you couldn't make out who it was so you mistook the person for your friend and went straight for a hug. 

"Woah. If coming to meet you gets me more hugs than I'll gladly visit you more often, [Your Friend's Name]" A deep, familiar rang through your ears  as the person you hugged responded. You immediately pulled back and threw your drink at him, acting purely on instinct. You slowly open your eyes and  come face to face with the only and one notorious Dean Winchester, who was drenched in your beer.  

"[Your Friend's Name]! What was that for? Wait a second.... [Y/N]..?" His eyes widened ever so slightly in surprise. You rolled your eyes at him.

"No shit Sherlock. I think I know what's going on here." Obviously your friend had tried to set you up on a date with Dean. You and Dean go way back but as for the moment, you really didn't want bring that history back. Dean looked at you as if asking for an elaboration.

"Well I think [Friend's Name] try to set us on a date. Okay mostly me since I just broke up with my boyfriend. You're just a pawn." Dean looked pretty offended when you called him a pawn. Then the two of you fell into an awkward silence. Oh could it get any more awkward? Apparently it could. Dean cleared his thoart,

"Since we're already here, we might as well catch up." you shook your head vigourously.

"Nope, Nada, NO! Dean!"  He was already pulling you to the dance floor even before you could stop him.  You stood there awkwardly while Dean took your hands and urged you to dance.

"Dean....you know I can't dance!!" He rolled his eyes, not believing me. 

"Really, [Y/N]? Remember that time you won the drunk country dance party at Garth's house?" You scoffed, remembering that party. You could barely call it a win. All of you at the party was smashed and all you did was swing your arms around and the rest had passed out so you won by default.

"That was a stupid party and competition, Dean." You tell him, feeling annoyed. You really didn't want to bring up the old memories you and Dean shared. You then drop your hands and walked away from Dean. All of the memories were getting harder to push back and it was just too overwhelming. You quickly get into your Cadillac and drive off to your apartment. In the rearview mirror, you could see Dean running out of the bar and you saw how heartbroken he was. Ignoring all that you continued to drive away, pushing all the regret away.