There is a sign posted on the front door of a small diner in a place called Lawrence. Originally called Old Roy's, it went out of business in the late 90s and sat there until the second owners rolled in. The first year was rough, but just three months after its opening, a food critic wrote up that sign and taped it to the window.
Best Pie in Kansas!
Now, the owners were by no means arrogant about it, but that extra boost of confidence from the sign was what they needed to kick off their business. See, the Winchester brothers had such little experience in restaurant management and business in general that it was really quite the puzzle to pull the diner off well, but that didn't stop them. It was no small or strange thing that they pursued that career, not at all; in fact it was the driving force in their lives to make it work. Time for a little history lesson.
The boys had been raised by their mother, Mary. Their father had vanished when the youngest of them, Sam, wasn't old enough to remember him at all and Dean, evidently the eldest, only had a vague impression (that one cruddy photo album is practically the only thing they know of him). Mary never explained where or why left, leaving the boys nothing but a "He just isn't coming back" to ponder.
The decades that followed were filled with a brilliant mother's love. Sam and Dean were happy kids that couldn't have asked for more, despite having a non-existent father. As they grew up, Sam took a keen interest in academics while Dean fell behind. He managed to pick odd jobs here and there, construction and whatnot, but it was hard for the older boy to hold anything down.
So Sam went to college and Dean stayed at home, helping out his mother and doing what he could to bring in money. In the summer of his 24th year, Dean met Cas. Things changed dramatically for him, then; they fell in love and he yearned to move out. But something was holding him back.
Little did Dean know but Mary had been harboring a very serious cancer. Her inability to function on her own was gradual, and at first Dean assumed it was her getting older or perhaps Sam's leaving, but once she got the diagnosis, he was devastated. They were all devastated.
It would be cruel to continue on with these minor details, since most people know how it feels to watch a loved one decline. The important take away in this history lesson is that Mary had, the whole time she raised her boys, talked about something; she always wanted to run a diner. She had worked in plenty, sure, since as a single mother she took every job she could, often leaving Dean in charge to watch his baby brother late into the night. It was painful and she dread it, but she did what she had to do, and self-sacrifice was what she was best at.
Watching his mother die, happy that her kids were content with what she had done but still clinging to that wish of being a restaurant owner, really warped Dean. For days after Mary passed, he would pace up and down the street, cursing to himself and screaming at the heavens for a way to make it up to his mother. In the midst of chaos, Sam had taken a break from school and come back home to stay with Dean. Well, Dean and Cas. Before Mary got terribly sick, the two had married and they were living in the old house together.
So once again, the Winchester brothers were together but now Dean had a husband. Cas had finished culinary school and was looking for work in that realm. As they wandered about town one day, Dean noticed the Old Roy's diner, abandoned for so long, FOR SALE sign fading in the window. And that's when he had the crazy idea. Sam stayed home much longer than he expected, and by the time that Dean was 27, the diner was up and running under its new name; Mary's.
"All I'm sayin' is if you were ta put a stand outside the emish'ns testin' facility, sellin' new gas caps, ya'd make a killin'. You git that, boy?"
"Um…sure, Bobby. Whatever you say."
Sam was the only waiter at Mary's Diner and often subject to the useless banter of their customers. He couldn't possibly talk trash about Bobby, their first and best regular, but when he got into the "car stuff" it was really hard for Sam to follow. Dean dug that type of talking better, but he usually slipped away from the register and popped his head back into the kitchen to watch his husband fill the orders.
"They always fail," Bobby continued as Sam refilled his coffee. "So why not make a li'l profit off that? Saves ev'ryone time and ya make some money."
"I don't know if it's legal to sell anything on the emissions testing facility," said Sam.
Bobby just rolled his eyes and muttered, "Law school types" behind his beard. It couldn't be helped. Sam shrugged it off and went to check on the only other customer in the diner. It was just a little before the lunch rush would come in so they still had time to relax.
Once Bobby had run out of gas cap chat to bitch about, Dean conveniently reappeared from the kitchen with a smile on his face. "Hey Bobby," he said. "My brother treating you alright?"
"Yeah I guess," Bobby groaned. "He just don't git it like we do."
"Mmhm, right. Hey you want your check now?"
Bobby grumped. "Dang it, Dean. What'd I tell ya 'bout askin' people fer their checks too soon?"
"Not to?" Dean asked, frowning.
"Yer a nice kid but I ain't too sure about ya runnin' a restaurant."
"Woah, hold on a second," Dean said, folding his arms and coming as close to Bobby as he could with the countertop between them. "I've done great for a year."
"Yeah an' I'm proud of that."
"Well thanks, Bobby."
The older man took a sip of his coffee and set it down, smacking his lips. "Surprised, though."
"Oh, thanks," Dean added. Before anymore could be said, the little bell tied to the front door chattered as a new patron stepped inside. Sam immediately jumped up from the table he had commandeered and greeted them. Not long after they had a seat, two more people came through. Sam took down all their orders and handed them off to Cas, just before grabbing water for them. Dean propped his chin up on the ledge and watched Cas as he poured frozen French fries into the deep fryer. "I tell you how sexy you look when you're back there?" Dean asked, smirking.
"Yes," Cas answered shortly, looking back at Dean real quick. "Every day, I think."
"Heheh, alright, well, you look sexy when you're back there."
"Thank you, Dean. Here, the starter salads for table 3."
"Right, right," Dean yawned. He took the plates and turned around, yelling "Hey Samm-yyy!"
"I'm right here, Dean! You don't have to yell."
"But I like to."
"Yeah I know you do." Sam shook a wisp of hair out of his face as he was handed the salads, not before giving his brother the check from the earlier guest. "Thanks," he said quietly.
"Good job, Sammy," Dean grinned, patting his brother on the shoulder. He took the money and rang it up into the register. The bell chimed again, this time bringing a group of four into the diner. They looked around with pleasantly surprised faces. Sure, from the outside, Mary's Diner looked like a dump. The lines in the parking lot needed to be repaved and it wouldn't hurt to have a power washer knock some of the dirt off her outside walls, but within the building was a quaint little slice of heaven.
"Hey uh, Sam will seat you," Dean said quietly to the people who just walked in. One snorted to another, standing there awkwardly. "Hey Samm-YYYYYYYY!" Dean called out.
"Hold on, hold on!" Sam whined. He was in the middle of jotting down another order.
Bobby, still at the counter, drummed his fingers on the handle of his coffee cup and looked at Dean with a smirk. "I think y'all should consider hirin' another waiter."
"Yeah, you think?" Dean groaned. Bobby put a five down on the counter and slid out of the chair, tipping his baseball cap to the not-so-efficient owner.
Finally Sam gave the orders over to Cas, then seated the four people at a booth in the back. He grabbed yet another finished order from the kitchen and gave it to another table. All the while Dean just stood behind the counter, watching his husband rush about in the kitchen.
"Dean, come on," Sam said, coming up to the counter.
"What do you mean come on? You come on. Those people were waiting for like two minutes while you took that other order."
"No I mean come on, hire another waiter."
Dean raised his eyebrows. "You uh, you heard Bobby?"
Sam shook his head. "No. What?"
"Nevermind. But I mean yeah, yeah I think we should start looking."