Just roll with it - Dean

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Fluff (And jealousy ;) )

Not dating!

Y/n was sitting on the bed in the motel room, scrolling on her phone. She was stalking, not just anyone but her ex-boyfriend. They used to date back when she just got out of high school. And a lot has happened since then. Sure, she has always been a hunter, but now it was her full time job. She worked with the Winchesters after Bobby Singer had introduced them, and the three of them hit it off right away. Sometime Y/n missed her old life, her old boyfriend. He was a dick, but he was the only real relationship she's ever had. Now she just hooks up with random guys and then leaves the next day for another hunt.

Reminiscing about her old boyfriend was normal for her. He was a lot of her firsts like her first relationship, first kiss, hell he was the first person she ever had sex with. As she continuously scrolled his social media wondering what he was like, now Dean got back to the motel. Entering their room, he was met with his best friend, laying across the bed glued to her phone.

"Hey y/n/n what are you doing?" She looked up, a little startled. "Oh, nothing," quickly she put her phone away. A little too quick in Deans opinion. "Uh huh," he looked her up and down with suspicion. "Seriously, Dean, I wasn't doing anything. What'd the witnesses say?" She asked, trying to change the subject.

Dean gave up, even if he did know something was up he knew she wouldn't tell him. "Apparently all of the victims went to the same art gallery," Y/n raised her eyebrow intrigued by the new information. "and?" she asked wanting to more. "And they all bought paintings by the same dealer," He responded. "I guess it makes sense, maybe a cursed painting, or a haunted artwork?" She thought out loud. "I was thinking the same thing," Dean grinned and y/n felt her heart beat a little faster. Even if she knew Dean never saw her in that way he has always made her a little weak at the knees as Bobby would say. "Well let's pay this gallery a visit then, how do you feel about a little sight seeing?" Y/n joked, "Well the place is hosting one of those fancy banquet things tonight, I thought we should go and have a look around." Dean noticed Y/ns eyes light up, he knew she would like that sort of thing. Sure, they could go right now instead but this seemed more fun. "You hate those kinds of things dean, you sure you don't wanna go now?" She asked, sure she wanted to go but if it made Dean uncomfortable then she wouldn't make him go.

"No, I think it might be fun you know?" He looked at her with a nervous smile. "Okay! I'll have to find something to wear, what time is it at?" She beamed excited, which made Dean happy. "It starts at six," Y/n noticed Sam wasn't around, hell she hasn't seen him all day. "Where's Sam?" She asked eye brows pinched together a little worry tainted her face. "Oh, he'll come too. He's at the library being a nerd." Dean chuckled, and y/n smiled. She thought back to her ex for a moment, and his pretty blonde hair. She silently wished it was him sitting here with her laughing about Sam being a geek. She had Dean though, she tried to convince herself all she needed were her bestfriends but something always felt like it was missing.

"You sure your good?" Dean interrupted y/n from her sulking. "Yeah I'm fine, just uh tired from the research last night." She tried to cover her tracks. He didn't buy it but decided to drop it anyways, if she didn't want to talk to him she shouldn't have to. Even if it did hurt a little knowing she was keeping something from him.

Looking in the mirror y/n was putting on some more blush, she really did love to do her makeup and dress up but being a hunter you didn't really have any excuse to, plus if she was being honest she was worried the guys would judge her for it. Tonight though she got to add a little extra makeup, she really did feel like she looked gorgeous tonight. Which she did. She wore a simple black dress but it made her body look desirable, or at least in her opinion it did. She usually doesn't feel comfortable in her own skin, she had a bad habit of picking at her every flaw. In her eyes there was to many to count, she believed it was the cause of her lack of male attention, when in reality she was always with Sam and Dean. People just assume she is together with one of them.

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