Dean, Sam, and Castiel spent the rest of the day catching up, watching TV, and searching for any signs of other supernatural creatures in the area. It seemed there were none and they were all happy to stay in the motel room. When night fell though, Dean began feeling cooped up. He got up from his bed and grabbed his leather jacket off of a hook on the wall.

"Why don't we go to a bar in town?" he asked.

Sam and Castiel glanced at each other and then followed Dean out of the motel room. They all hopped into the Impala together and found a bar called Darlene's on the other side of town.

When they entered the three men headed straight for the bar and sat down on the stools. Sam and Castiel sat so that Dean was inbetween them.

"Hello," the pretty blonde bartender greeted them. "What would you like?" She winked at Castiel and Dean chuckled as his friend's cheeks gained color.

"Three beers from the tap," Dean told the bartender.

The young woman nodded and turned her back to them so she could fill up three mugs.

Dean nudged Castiel's right arm with his elbow. "She's into you."

Castiel shook his head as the woman passed them their beers and took a sip from his mug.

Just then, the front door to the bar opened and Castiel and the Winchesters looked up to see who entered.

Castiel's breath caught.

The young woman who was coming into the bar was beautiful. She was a couple inches shorter than him but had long slender legs. Her brown hair was golden highlighted, bouncy, and reached her middle back. She was dressed simply with dark blue jeans that hugged her body and was wearing an equally tight white sweater. She looked amazing in it and Castiel couldn't look away. His eyes widened when he realized she was walking up to him and the Winchester brothers.

"Hey, Sam and Dean!" The woman grinned as she plopped herself down on the empty stool next to Sam. "Long time no see." She turned to the bartender quickly and asked for a whiskey shot.

When she was given it, she swallowed it in one chug before facing the guys again. "So are you going to introduce me to your friend?"

"This is Castiel," Dean said. "Cas, this is Emily Stelling."

Emily gave Castiel a friendly smile. "Nice to meet you."

He nodded back. "You too."

Emily then took her eyes off of him and let them fall on Sam. "So did your leg heal up alright?"

"Yeap, no limp," Sam answered.

Castiel frowned. "What happened to your leg?"

"Werewolf," Sam replied simply.

"It was a while back, in March," Dean continued. "Some werewolves trapped us in an alleyway and one broke Sam's leg."

"Yeah and I saved their asses." Emily smirked. "Never expected to meet the famous Winchester brothers I hear about all the frickin time bloodied and pinned down by two werewolves."

Castiel laughed. "I just saved them from a few vampires yesterday."

Emily's glaze was drawn to him then back to Dean and Sam. She whistled. "You guys are getting rusty in your old age."

"I'm not that old," Sam protested.

Dean starred at him. "Are you saying I am?"

"Well, you are fifty-two Dean," Sam snickered.

"Well you're not a spring chicken either you know," Dean argued. "Do I have to remind you you're only four years younger than me?"

Emily burst out in giggles and tears sprung to her eyes. She quickly wiped them. "You two are hilarious."

"Glad we could be the comedy act of the night," Dean said sarcastically as he rolled his eyes.

Castiel and Sam laughed.

"So besides playing damsels in distress what have you been doing?" Emily inquired.

Dean sighed. "Nothing much. Same old same old."

"That's a very good thing in our line of work," Emily concluded as she peered past Sam, Dean, and Castiel to the pool table in the back of the room. Two men dressed entirely in leather were setting it up to play a game.

"Well, I think I'm going to go play some rounds of pool," she announced. "I need some cash. Nice seeing you again. Nice meeting you, Castiel."

Castiel nodded.

Emily smiled. "Wish me luck."

She walked away and Castiel couldn't help but watch. Dean caught him in the act.

"Why don't you go ask her out or something?"

"Huh?" Castiel craned his neck to see Dean's face.

"You like her," Dean said. "And she's your age. You should go ask her out."

Castiel glanced back nervously at Emily then took a sip from his mug. He avoided Dean's glaze because he knew without looking that his eyes now held confusion.

Dean cocked an eyebrow for a moment and then it dawned on him. "No way. You are not still a virgin."

Those words caught Sam's attention and his eyebrows lifted as he finished off his beer.

Castiel kept quiet but his flushed face gave the answer away.

Dean couldn't believe it. "You've got to be kidding me."

"I never got the chance to date a girl okay?" Castiel defended himself. "I was about to ask Taylor out when I found out the truth about my past and decided to begin hunting."

Dean tilted his head towards Emily's direction. "Well there's your chance."

Castiel watched as Emily leaned over the pool table and hit a red ball into a pocket. "What should I say?"

"Do you know how to play pool?" Dean questioned.

"Yes, my parents had one in the basement," Castiel answered.

"Good," Dean said. "Do you have any money on you?"

Castiel gave Dean a strange look. "Yeah."

"Then go place a bet and play a game with her," Dean told him. "It's the perfect ice breaker."

"Alright."

Castiel hesitantly stood and slowly made his way over to the pool table.

Dean gulped down his drink until he noticed Sam watching him. "What?"

"You and your dating advice."

Dean rolled his eyes.

"Mind if I play a game of pool with you?" Castiel inquired as Emily began counting the money she'd gotten from the bikers. They hadn't expected that a girl could play so well.

Emily shrugged. "It depends what you're willing to lay on the table."

"I have thirty dollars on me," Castiel said as he pulled out his wallet.

He threw the money down on the green velvet of the table and Emily smiled slightly. "I'll take your bet."

She set up the balls and passed Castiel a cue stick. "I'm warning you; I'm good."

Castiel chuckled. "I'm sure you are."

Emily let Castiel break and he sent four balls into two different pockets. Emily then hit three.

"I only get better from here on out," she promised as she backed from the table.

She had so much confidence. No wonder she could survive being a hunter.

It was five minutes into the game when Emily casually asked Castiel where he came from.

"Illinois," he replied. "You?"

"Texas."

"Do you have any family back home?"

Emily sighed. "Just my older sister, Beth. She's a teacher in Dallas. Do you have any?"

"My parents, and I have a younger sister named Holly," Castiel told her.

She nodded.

They played a couple rounds in silence before Emily spoke up again. "How'd you get into hunting?"

Castiel froze in the middle of a shot. The ball he was hitting moved a mere inch.

He wasn't sure what to say. Should he lie?

Castiel decided that he had no choice. She'd think he was crazy otherwise.

"I just kind of stumbled into it after Dean and Sam saved my family a while back from a demon. How did you get into this business?"

"I lost my brother, Mitch, to a shapeshifter," Emily answered sadly.

Castiel instantly felt bad for her. "I'm sorry," he apologized.

Emily forced a smile. "It's okay. It happened two years ago."

"Still, it must have been so hard for you."

Castiel realized just then, that he had moved closer to Emily then he had been the whole night. He was so close he could have touched her face. He could feel her breath on his skin.

His eyes met with her beautiful emerald ones and they both froze. Castiel heard Emily's breath catch as his heart sped up.

He found himself leaning forward, towards her, but she broke their eye contact and turned to the pool table.

Castiel awoke from his trance and watched as Emily hit the black ball into the hole across from her.

She turned to Castiel with a grin on her face. "Looks like you're broke."