Imagine Sam and Dean encouraging Bobby to ask you out.

Word Count: 540

~ Third Person POV ~

Bobby, Sam, and Dean sit at a table in a respectable bar run by a sweet girl named Y/n. The ensemble have yet to order, as they just arrived a few minutes ago. 

The h/c haired woman comes to their table with a notepad and a pencil. "The usual, Bobby?" She asks, a huge smile on her face as she awaits the answer.

"Um, yes, thanks," he smiles back to her. 

"How about you two?" She redirects her questioning to the two boys with Bobby. 

"I'l take a cheeseburger and a beer." Dean says.

"I'll have the same, thank you," Sam adds, and the waitress nods. 

With another bright smile, she leaves to place the orders and get the drinks. 

"So, Bobby, you come here a lot?" Sam initiates conversation.

He nods, eyeing the waitress as she walks back with a tray of drinks. She carefully places the drinks down and informs them that their food will be done shortly.

"I bet I know why," Dean comments, sending a smirk to Bobby.

"Really?" He asks, taking a drink of his beverage as he continues to follow Y/n's moves with his eyes. 

"Oh, yeah. You like her." 

"What?" Bobby says in disbelief. "No!" 

Dean smirks and looks to Sam, "Sammy sees it too, don't ya Sammy?"

"Yeah." Sam says, but decides to stay out of the conversation as much as he can. 

Dean smirks and swigs his beer, "You should ask her out before someone beats you to it." 

Bobby shoots him a glare as Y/n returns with the food and sets it on the table. 

"Anything else I can get you?" She smiles, particularly at Bobby. He smiles back at her, about to say no, but Dean interrupts. 

"Yeah, actually-" He's cut off as Bobby kicks him in the shin.

"No thanks, Y/n." Bobby answers.

She smiles, "Well, you know where to find me." With a wink, she walks off to help the other customers. 

"Oh, Bobby, she's into you." Dean laughs as he digs into his food. 

"You think so?" He asks, a dash of hope found in his voice.

"Think? Man, I'd know that look anywhere. She's got the hots for you, no doubt about it." 

Bobby looks to Sam for assurance, and Sam nods earnestly. Bobby grins and takes a drink of his beer. 

Having found his courage, Bobby excuses himself from the boys, "I'll be right back."

He makes his way to the counter where Y/n is polishing some cutlery. She grins warmly as he approaches.

"Hey, Y/n, I was wondering if..." He starts, but trails off as he looks into her e/c eyes that seemingly sparkle.

She chuckles in amusement, "Yes Bobby?"

"Oh, um, I was wondering if you're busy tomorrow night?"

"No, I'm not busy." She leans against the counter towards Bobby, "Why?"

He gulps nervously, "Well, I was thinking, maybe you want to get some drinks with me?" 

"I'd love to!"

He grins widely, "Great! I'll pick you up around seven?" 

"I can't wait," she smiles before quickly kissing his cheek. "But, right now I gotta get back to work. I'll see you tomorrow."

He watches her walk away to take more orders, "I look forward to it."

He walks back to the grinning Winchester brothers, with a smile on his face.