Chapter 29

A few days later Dean found himself in an awkward position. He was standing in front of one of those dressing room tryptic mirrors looking at his own reflection. Only he was not wearing anything close to what he considered normal.

Or comfortable.

He was in an old-fashioned, dark grey, pinstriped, three-piece suit in some 2nd hand store in the city center of the closest shopping district to The Roadhouse. A few dozen miles away. As per J's suggestion.

Dean sighed as he examined himself in the mirror, the different angles it added was not helping him decide which suit he was going to go with. This one certainly fits the best. He adjusted the collar. He always hated dressing up. It was the one thing Dean hated most about the job.

Playing some suit cop to get answers.

When J had asked him on a date to a Jazz Club, he wasn't expecting there to be any rules. Or a freaking dress code for that matter. For this reason, he was thankful Sam had agreed to come with him and help on his search for an outfit, as well as one for himself.

J had instructed him to dress the part. Meaning 1940's dress code. Also meaning Dean was entirely out of his depth and had no idea what he was doing or what he was going to do that night of the actual date.

If she had requested that he dress in this fashion, Dean could only imagine the club they were going to be meeting at. Or what J would be wearing. She must be going 1940s style, too. His mind began to wonder at the possibilities when Sam snapped him out of it.

"I think I like that one the best. It fits you perfectly and that color really brings out the green in your eyes." Sam offered without prompt as he adjusted his own suit.

"Aww thank you, Sammy. I am glad someone appreciates my eyes." He said sweetly back to his brother as he batted his eyelashes exaggeratingly at him.

"Hey, man. You asked me to come and help you with this. So, I am." Sam was busy staring in his own mirror adjusting the tie on his own three-piece find.

Sam had asked to come along to this 'new' club and J had agreed. This is the part where the rules came in. So long as Sam stayed on his side of the club, and did not interact with them and just left them alone, he was allowed to come, too. J had looked shameful when she admitted part of the reason why she had suggested this club, to begin with, was to get away from everyone. Sam being one of those people. She did not want him overhearing anything.

Dean was thankful that J was so laid back, forthcoming, and flexible. He thanked her for thinking of their privacy but also thinking of his brother whom he didn't want to leave alone at The Roadhouse. Especially, when there was a completely new place a few towns over, one they had never even known about, that he could tell Sam was seriously excited about checking out.

He also agreed that Sam needed to stay as far away from them as possible. Following J's confession to being a witch he had had his own freakout, unbeknownst to J, in the shower that night. She had confessed to him about being a witch. How exactly was he supposed to handle that information? How was he supposed to expect Sam to handle that information when the time came?

He himself had spent so long in the shower going over everything, that he had failed to even notice the water running cold. Only Sam pounding on the door brought Dean back from his slight mental break over understanding and dealing with the information presented to him. It unnerved Dean as much as it intrigued him. He had so many questions.

Sam being Sam knew something was up, as he always eventually picked up on whatever it was. Dean knew he would figure it out on his own. Sooner rather than later. He just hoped J got to him before Sam came to his own conclusions. He knew the conclusions he himself would have drawn. Based solely on the information of observation. He could only imagine how Sam would feel about all this.

Dean was more than desperate to ask more questions but was kept from doing so because his giant of a brother was usually around, and mum was the word at the moment. Best to act like nothing changed. Like no new information had been shared. At least at this new place, there would be a lack of hunters to overhear, too. He did not think that was a coincidence or an accident.

J may have had many more reasons for picking this particular place than Dean previously considered. First, he thought it was just to get away from Sam, Ellen, and Jo. He also considered it a mischievous way of getting him into this monkey suit.

If he was being honest with himself, this was not half bad and he was really looking forward to what this night would bring.

Dean was even nervous. To an extent. Only to an extent, he would admit to, of course.

This date would give Dean the chance he wanted to get to know as much about this enigmatic woman as he could. A freaking witchy woman. He was also secretly hoping it would go well enough to earn a second date. Though, he was wearier of this hope due to his serious lack of legitimate dates he had been on. He just knew he wanted J to like him.

So, when he was given a time, place, and a dress code, he had not objected at all. Until he completely wrapped his head around what a dress code entailed. There was a small panic attack at the realization of what he had agreed to at that point. It was then he had gotten Sam involved. Only telling him about the date and nothing more.

Not that Sam needed any more information than that. He actually seemed kind of relieved when Dean told him about his and J's date. Now here they were, both looking like they raided their grandfather's closet that had not been touched in half a century.

One of the shopkeepers came up with a pair of hats. She had been key in helping them both find proper attire that would at least pass for a Jazz club in the 1940s. She was very knowledgeable about the fashion and what she had in stock that would work or would suit their needs.

It had been a lot easier for Dean than it had been for Sam. Due to his height, the shopkeeper had to make do with some modifications to other garments to bring Sam's outfit together. The end result was the same. Two dapper gentlemen who just needed a couple of pretty dames on their arms.

Both Sam and Dean looked like the definition of the phrase The Cat's Meow. Dean took the old Stetson Fedora from the shop keeper and put it on his head. Suddenly the look was complete. A pair of dress shoes and he could have just walked out of one of those old black and white crime movies.

Sam took the other hat, a newsboy cap, and placed it on his head.

The brothers looked from their reflections to each other. Sam smiled at him. Maybe this wasn't a bad idea. Maybe this whole dress code thing wouldn't be the end of the world after all.

Dean took another look in his mirror, this time from the side, and smirked at his own reflection.

Damn, I clean up good.

Sam and Dean walked into the dimly lit jazz club called The Red Lady at 8 PM later that night. It was almost as if they had stepped back in time. Right into a Film Noir. Only in full color.

There was a live band with a very pretty strawberry-blonde in a red sequin dress singing an old jazz tune in the back corner. Her dress glinted like Dorothy's ruby-red slippers in the light of the spotlight. There was a dance floor in front of the small, raised stage. A chandelier hanging above it rather than the usual disco ball. There were a few couples dancing almost swing-style to the upbeat tune of the song.

Along one side of the club ran an old-fashioned mirrored bar. It ran the entire length of the room. Most of the barstools were already taken with patrons who all seemed to have been plucked right off the streets of the 1940s and dropped here. It was a good thing they had taken J's advice on the 2nd hand shop, and the dress code. It didn't seem like there was a single person in here from the current century.

High-backed booths clad in black leather ran along the opposite wall and there were a dozen or so small tables between the bar and the booths leading up to the dance floor and stage. The chairs at the tables were upholstered with what looked like red velvet, the same as the barstools at the bar. About half of the booths and tables were already taken, even at such an early hour.

Dean noticed Sam do a double-take on the strawberry-blonde up on the stage as they scanned the room. It was starting to look like he wouldn't have to worry about Sammy getting lonely and feeling like a third wheel tonight after all. The singer had seemed to take notice to the giant that was his brother already and there was now a flirty smile on her face as she finished the last of her song.

The bar quieted in conversation as the audience clapped.

"Bar side of the room is your side; booth side is ours. The dance floor is neutral ground. I'm supposed to be meeting J here at the front. It sounds like she either had a table or a booth already reserved." Dean looked over at Sam to make sure that what he had just said had registered, then past to the strawberry-blonde now staring his brother down from the stage as she started her next song.

Sam nodded in agreement, barely listening to Dean, eyes fixed on the woman in the red dress. "If we need to contact each other call or text. Blah blah blah. We already went over all of this like 100 times. Just relax and have fun. Get to know J better. I know you have been dying to since you first met the chick. I'm glad she seems just as eager." Sam said quickly, with a hint of annoyance in his voice.

"Go and have your first REAL date." He teased, with a short laugh, over his shoulder as he walked towards the bar and away from Dean.

Dean watched him walk to the end of the bar that was closest to the stage and take the stool at the very end. The Lady in Red up on stage watched Sam just as carefully as he walked over, took a seat, ordered himself a drink, and turned back towards her and the stage.

Now Dean was just standing to the side of the bar with his hands in the pockets of his trousers. He had been told, all via text, that J would be coming and collecting him from this spot shortly after they arrived; and Sam had gone off on his own. But he also remembered that night at The Roadhouse where he hadn't even recognized her at first.

Dean's eyes slowly scanned the small crowd, determined not to make that mistake again. He analyzed the face of every woman he could see and came to the conclusion that J was not here yet. The question still remained. Would he even recognize her tonight when he did see her? He barely recognized himself when he looked in the mirror behind the bar. Slicked back hair under a dark, midnight-blue fedora, matching three-piece suit, and shoes that had an almost mirror-like finish from the amount of buffing he had done to them.

Dean had definitely put a lot of effort into his appearance tonight. Which was saying something. So much so Sam had even made more than a few comments, calling him Deana. The truth was he had been thinking about that night with that Pretty Boy Witch at The Roadhouse. J was capable of being The Drop Dead Gorgeous One in any room she wished to be in.

He wanted to look good. He wanted J to think that he looked good. That they would look good together… He felt like he looked good. Maybe not as good as he would have hoped. All things considered; Dean Winchester cleaned up nicely. But if J was capable of looking like that, how she did that night at the Roadhouse,she deserved a date who looked, or at least was trying to look, just as good.

At least the looks he was getting from some of the female patrons, and even some male ones as well, were boosting his confidence more and more as the minutes passed. Dean felt like he was doing more than satisfactory at at least looking the part. He turned to the bar to order a drink while he waited when he felt a tap on his shoulder.

A very pretty blonde was sliding onto the barstool at the end of the bar right next to where Dean was standing. He had not noticed her walk up next to him somehow. He must have been more preoccupied than he thought. He was certainly distracted, trying to spot J before she magically appeared next to him.

The new-comer eyed him up and down hungrily and without hiding it. Dean smiled when he realized there was no difference in height when she was sitting down on the barstool versus when she was standing up.

This stranger must have taken that as her cue.

"Well, hello there, big boy. I don't recall ever seeing you around here before. My name is Madison."

Dean rolled his eyes so hard inside he was surprised that he had kept himself from actually physically doing it. He felt annoyed by this woman already. His interests were not even in this room. Not yet at least. Even if he were here on a mission to pick up his usual next one-night stand, this already-drunk woman would not be his first, second, nor even third choice.

"Hello, Madison. My name is Dean. I'm actually- "

"We'll have two whiskeys over here!" Madison rudely called to the bartender, effectively cutting him off at the same time. Dean saw the frown under the bartender's pencil mustache as he grabbed two glasses, eyeing them both.

Dean made eye contact with him and motioned his apologies. "Make that a double." Dean added, throwing a bill into the tip jar. The bartender gave him a small smile. The bartender could tell when a fellow was in over his head. And Dean was certainly there.

"Coming right up, sir." The bartender said as he grabbed a bottle of amber liquid.

All Dean had time to do was look back at Madison before the bartender was in front of them with the two glasses and a bottle of whiskey.

"Neat or on the rocks?" Asked the pencil-mustache-clad bartender.

"Neat." Replied Dean at the same time Madison said "On the rocks."

They looked at each other and laughed. Madison was laughing at the fact that they had spoken at the same time, Dean was laughing at the fact that this woman liked watered-down whiskey.

The bartender handed Dean his double whiskey and poured some ice into Madison's glass before pouring her drink and handing it to her.

Madison must have mistaken Dean's mocking laugher as flirtatious laugher. She grabbed her glass and took a sip, eyeing him the whole time. A smug look in her eye.

She set her glass down on the bar and leaned into Dean as he went to take his first sip, gulp maybe, of his own whiskey. He pulled his glass away and physically leaned away from her as she got uncomfortably close. Did this chick seriously not get personal space?

"So, what is a fine gentleman like yourself doing around these parts. It's not too often we get a newbie here. Particularly one of your… caliber…" she tried whispering in his ear. She trailed off as she took another swig of her drink. The ice shifting in the glass, spilling some of the amber liquid over her chin.

So, this is what it's like to be a woman. Oh, my god… Dean thought to himself, half mortified, half shocked.

"Actually, I'm here meeting someone." Dean said, thankful for this to not only be true but also for how fast Madison turned from being perfectly friendly to downright cold.

"You could have said something, asshole." She said as she stormed away.

"You didn't give me a chance to really say anything." Dean said more to himself than anything as she stomped away. He pulled out his wallet again to retrieve more money to pay for this round of unexpected drinks. He took a few bills and threw them over the counter of the bar when he made eye contact with Pencil-stache again.

As Dean was putting his wallet away, he looked back up to the stage at the back of the club. His plan was to find his brother and assess how he was doing with the pretty singer in the red dress. He did not plan on looking over and seeing J blowing a kiss to said strawberry-blonde as she walked towards the dance floor on the opposite side of the club.

There was no way Dean could have missed her. Even if he had tried.