The next few hours were spent pouring over every music sheet in the building. Dean had Y/N sing a few more songs in a few different styles, claiming he needed to know what best suited her voice. She was suspicious, but said nothing.

By noon, the bartender, Castiel, entered with Meg. She was wrapped around him like vines on a house, but they separated when they saw that they weren't alone.

Dean had shouted across the room that the private rooms were in the back, and Meg had sent him a glare that, for all intents and purposes, should've killed him.

Meg disappeared into the kitchen behind the bar, whilst Castiel took his post and began prepping for the evening.

Around two, Dean decided that it was time to take a break and give Y/N's voice a rest. "Plus, it gives me an excuse to buy you a drink!" he'd winked.

"Well, I'm not one to turn down a free drink!" Y/N smiled, already enjoying this day a thousand times more than she thought she would.

He held out his hand to help her off the stage, and she took it, both of them ignoring that she didn't need the help and the fact that there were stairs off to the side to make for easy access.

They walked up to the bar, and Castiel smiled. "Good afternoon, Dean." He bowed his head slightly.

"Heya, Cas. This here's Y/N Y/L/N, the new singer."

"I assumed as much." Castiel turned to her. "It's a pleasure to meet you, Miss Y/L/N."

"Please, just Y/N's fine."

"If you insist. I am Castiel Novak."

"You can call him Cas," Dean finally took a seat on one of the stools.

The second Dean sat, Castiel began pouring a shot of whiskey for the pianist. Dean downed it all in one go before putting it back down on the bar. That was apparently Castiel's signal to refill, as that's what he did next. Dean turned to Y/N before motioning to Castiel with his head. "What about you, doll?"

Y/N frowned. "I can't have anything too strong, unfortunately. How 'bout a Shirley Temple?"

"You a lightweight?"

Y/N laughed, but Castiel answered. "It's not good for her voice, Dean."

Dean's ears tinged a little pink. "I-I knew that, Cas. Jus' askin' a question, that's all."

She sat down next to her bandmate as the bartender slid her drink to her. "Thank you, Castiel."

"You can call him Cas."

"When he says I can, Dean."

"I do not mind, Y/N. Whichever you prefer is fine with me."

She huffed. "Well, if you're sure it's okay."

He shrugged, pouring another shot for Dean.

"Alright, well then, thank you, Cas," Y/N smiled.

That was the moment Meg walked out of the kitchen, now in a white shirt and black skirt that were barely appropriate that Y/N had to assume was her uniform. Her brown hair was swept back beautifully, framing her face, but keeping it out of her way. Her chocolate eyes landed on the three at the bar, and her perfect lips pulled back in a smile. "Howdy folks!"

Castiel smiled softly at her, whilst Dean raised his drink towards her. "Meg, Y/N. Y/N, Meg." He said in the way of introduction.

"Ah, new singer, right?"

Y/N stood and held out her hand to the new girl in the room. "That's right. And you're the head waitress, right?"

"That's right," Meg nodded and shook Y/N's hand firmly. "Don't worry about meetin' the other girls. They come and go so fast, even I can't keep track of 'em all."

Y/N's eyebrows shot up at that. "Wow…how do you get anything done then?"

"No clue," Meg grinned.

Y/N chuckled in disbelief at that. "Well, I can't wait to see how you do it."

Meg grinned, heading behind the bar. "Same here. Cas and I heard you both a bit when we came in, but I'd like the full effect." She walked over, placed a quick kiss on Castiel's cheek, then leaned over and placed her hand over Dean's drink.

"Hey!"

"How many have you had, Dean-o?"

He grumbled, but Castiel answered. "That is his fourth shot."

"Then less drinking, more practicing."

The pianist grumbled, but stepped back from the bar. "Fine. C'mon, Y/N, let's give 'em a show."

The day went by quickly as everyone else filed in. Chuck came in, introduced himself quickly, then reintroduced himself to the bar and Castiel.

After a drink, he was up on stage with them, fine tuning a few songs with them. He seemed a bit squirrely but otherwise rather nice. He was shorter than the other men in the club, with brown scruff to match his rather matted hair and tired eyes.

About an hour before opening, Gabriel swaggered in, his blonde hair half gelled back and half standing up at different ends with lipstick stains on his face and lapel. His hazel eyes shone with glee, seemingly proud of himself. He waved to Castiel, winked at a few of the waitresses, then made his way backstage, completely ignoring the new addition to the band.

Dean and Chuck seemed unsurprised by this, so Y/N said nothing.

When he finally came out, he smiled flirtatiously at the new singer. "Hola, mi amor."

She didn't even get a work out before Dean interrupted. "Don't even think about, Gabe."

Gabe threw a confused look at Dean, before grinning. "Ah. Okay. Read ya loud and clear."

Dean glared at his bandmate, trying to hide the pink tinging the tips of his ears. Y/N bit her bottom lip, suddenly slightly more hopeful.

"C'mon, let's get started, slackers!" Gabe grinned, taking a seat behind his drums and beginning to play.

Y/N's eyes widened enough to nearly pop out of her head. He was amazing. He was mesmerizing. He threw himself fully into his music, the passion flowing out to touch everyone in the room. She couldn't hear anything except his playing, and she wondered idly if that was because she was mesmerized, or if because everyone had stopped what they were doing to listen to him.

When he stopped a few moments later, he turned to Dean and said, "Ready?"

Dean chuckled. "As always."

And, with that, they began their first full rehearsal.

The bar filled up within moments of it opening. The new band stood behind the stage, running through their final preparations before beginning their show for the night.

Meg had been lovely enough to pull Y/N aside about thirty minutes earlier and get her all spruced up. She had helped with her hair and they'd found an appropriate dress in the racks hidden away. It was elegant and hugged every curve of her body. It went all the way down to the floor, brushed against her feet in her shoes, the same shoes she'd worn to work earlier that day. Her Y/H/C hair was swept back and to the side, layering over her right shoulder. Meg might've gone a little overboard with the make-up, but she claimed that it would withstand the spotlight and that's what mattered.

It was worth it, though, when the girls exited the dressing room, and the boys looked at Y/N like they'd not seen her before. Dean especially looked like someone had knocked the breath out of him.

Meg had nudged Y/N's side, grinning. Y/N's now-red lips split to smile widely at the head waitress. Meg had then accepted Y/N's thanks and headed out to take care of patrons and the other girls.

The plan was for the boys to go up on stage before Y/N, then introduce the new singer to the crowd. Gabriel and Chuck had told her to break a leg, then headed out.

Dean's large hand landed softly on her left shoulder, and she looked up into his soft green eyes. He smiled warmly. "You're gonna knock 'em dead, doll."

Y/N nodded, refusing to let any nerves get to her. "I know."

Dean laughed at that. "And so modest!"

She shrugged playfully. "I know what I got, Winchester."

"Anytime you're willin' to share, doll, I'm all ears."

She looked up at him, a comeback on the tip of her tongue. That comeback died, however, when she locked eyes with him. She had expected some mischief in his eyes, or a salacious smile gracing his cheeks, and, instead, she was met with a serious expression.

She gulped and tried to ignore her heart beating in her ears. After a moment, she managed to squeak out, "You'll be the first to know, Dean."

He gave a genuine smile at that before lightly patting her on the shoulder. "See ya out there, doll." With that, he threw one last playful grin at her and headed out into the main room.

Y/N was left alone backstage. She heard the boys tuning their instruments once more mixed with the low murmur of the patrons as they filed and settled in for a night of fun.

"Nervous?"

Y/N nearly jumped out of her skin before she turned to see her new boss standing towards the end of the hall. She heard the click of his designer shoes as he slowly walked over to her. "There's no reason to be nervous, darling."

"I'll be great, Mr. Crowley."

His eyebrows raised slightly as he came to a stop beside her. "Good. That's what I like to hear from my investments."

Her jaw clenched, but she looked directly into his eyes. "I'll be great, Mr. Crowley," she said as evenly as she could, refusing to let him see her fear.

He smiled before turning on his heel and beginning to walk away. "Can't wait."

She breathed out a sigh of relief when he disappeared out into the main room. He hadn't been listening to their rehearsing all day, locked away in his office, and now she was a bit more worried. If he didn't like their performance, there went her freedom. Well, what little she had left. But the small amount of freedom Crowley offered her was better than nothing.

She heard Gabriel speaking now, thanking everyone for coming that night and promising them a wonderful time. Then, he introduced her.

"And tonight, you're all in for a treat. We've got a special songbird that starts tonight, ready to knock your socks off. Please welcome the lovely, the melodious, the amazing Y/N Y/L/N!"

She took one last deep breath as the polite applause began, then opened the door to the main room.

It looked quite different than it did empty, which shouldn't have surprised her as much as it did. The low light hid everyone's faces, though, so she could only make out builds and some outfits. Tables were laid out around the room, each filled with a few people. The booths had some men sitting there with girls wearing outfits similar to Meg's curled up at their sides.

Then, she looked to the stage, and she saw her bandmates. They were all smiling at her, and Dean was standing by the steps, his hand out and ready for hers.

She took it happily, relishing in the warm of the contact, before walking up the steps as the applause began dying down.

The spotlight and floor lights eliminated her ability to see even the outlines of the audience, which made her feel better.

She turned to throw one last look at her pianist, who winked at her, then began playing.