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Uptown Boy

Summary:

When mechanic Dean Winchester meets lawyer Castiel when his Rolls Royce breaks down in the rain in the fall of 1987, they fall for each other. But can they fit into each other's world?

This fiction was inspired by an amazing piece of art by girlinthemirrorbluenight for the Dean/Cas Reverse Bang. Please checkout her Tumblr here. Both the story and the art are inspired by the song Uptown Girl by Billy Joel.

Chapter Text

September 18, 2023

Claire called out to her wife, Kaia, “Dad and Pops will be here in about twenty minutes. Sam just picked them up from the airport.”

She walked into the living room where her kids, Deanna, Samantha, and Cassandra were hanging up decorations for their grandparent's thirty-fifth wedding anniversary. She smiled as her eyes fell on the picture of her parents, Castiel and Dean, standing side-by-side on their wedding day so many years before. She had been twelve, and it had been one of the happiest days of her life. She looked at her own daughters. Deanna was finishing putting up a banner over the doorway, as Cassandra and Samantha were arranging paper plates and party hats around a cake decorated as a '67 Impala.

Claire smiled, “You guys almost ready?”

Cassandra responded, “Just putting up the last few touches, Mom.”

Deanna rolled her eyes, “They are not going to like it. Grandpa Dean doesn’t like surprises.”

Cassandra argued, “He’ll like this one.”

Samantha asked dreamily, “Was it love at first sight? Did they meet in romantic places, like a garden? They’ve been married forever.”

“Didn’t I tell you how they met before? “Claire asked.

Cassandra responded, “I don’t think so. Didn’t you and Aunt Meg set them up?”

Claire smiled. “We didn’t set them up. We just nudged them a bit in the right direction.”

Deanna asked, pretending not to be interested, but she wanted to know, “It’s probably boring like they met at a library.”

Claire responded, “Not exactly. It was a dark and stormy night.”

 

October 1987

Castiel gripped the steering wheel tightly as he drove through the heavy rainstorm. The rain was so dense that it felt like he was driving through a waterfall, and he had to turn on his windshield wipers to their highest speed just to be able to see the road ahead. The windshield wipers worked furiously to clear his view, but it hardly helped. He was driving an unfamiliar car, and the dashboard lights started flickering, making him anxious.

Suddenly, a bolt of lightning illuminated the sky, making him jump in his seat. The thunderclap that followed was so loud that it rattled his car windows.

Castiel let out a shaky breath and tried to calm his racing heart. Ever since he was a kid, he'd been afraid of thunderstorms. His mother used to tell him that thunder was just the angels bowling in heaven, but as he grew older, the sound of it only made him feel more uneasy. He took a deep breath and tried to focus on the road ahead. But then, another bolt of lightning struck, this one closer than the last. Castiel felt his heart race even faster, and his grip on the steering wheel tightened.

The rain seemed to be getting heavier, and Castiel could no longer see more than a few feet. He slowed his car to a crawl, trying to keep it on the road as the wind buffeted it from side to side.

Another bolt of lightning lit up the sky, and this time it struck a tree just ahead of Castiel's car. The tree exploded in a shower of sparks, and he swerved to avoid the debris. He heard a dull thud as a branch fell on the car, and the car shuddered.

Castiel's hands shook as he tried to keep control of the car, and he knew that he had to find a safe place to pull over before something worse happened.

When he spotted the turn-off for a parking lot, he pulled in and stopped the car, grateful to be off the road. He sat there for a few moments, his heart pounding in his chest, as lightning and thunder raced across the sky. Castiel took a deep breath and looked out at the rain-soaked landscape. As he sat there, he couldn't help but feel a sense of awe at the power of nature, even in its most terrifying moments.

When the worst of the thunderstorm passed, he pulled back on the road. Just when he thought it couldn't get any worse, he heard a loud bang, and the steering wheel shook violently. Castiel knew at once that he had a flat tire. He pulled over to the side of the road, his heart pounding in his chest. He tried to remember the last time he had changed a tire, but it had been years.

He got out of the car and braced himself against the rain as he walked to the trunk. He fumbled with the latch before finally getting it open. His heart sank as he popped the trunk of his brother's car and saw that there was no spare tire.

He had borrowed his brother Gabriel’s Rolls Royce for the week while his more modest Chrysler was in the shop. He hadn't thought to check if it had a spare tire. He felt foolish for not being more thorough, but he was also frustrated at the situation he found himself in. Gabriel was never prepared for anything but somehow lived a charmed existence where everything just worked out perfectly for him. Castiel never had such luck.

He saw the lights of a small auto shop in the distance. He headed toward the light, covering his head with his trench coat as best as he could. His teeth were chattering by the time he arrived.

He opened the shop door and entered. A tall man with sandy blond hair was mopping the floor; however, he did it while singing along with a loud radio and dancing with the mop as if it was a ballroom dancer. The man sang slightly off-key but with gusto,

Uptown girl
She's been living in her uptown world
I bet she's never had a backstreet guy
I bet her momma never told her why

I'm gonna try for an uptown girl
She's been living in her white-bread world
As long as anyone with hot blood can
And now she's looking for a downtown man
That's what I am

He danced with abandon; his eyes closed as he sang. He seemed oblivious to how silly he looked because he was caught in the moment. As the song ended, he flourished the mop into a final pose and bowed with it. As he opened his eyes, he looked directly at Castiel. A blush radiated from his face as he said, "Oops."

Leaning the mop quickly against the wall, he strode over to Castiel. "Hi, I'm Dean. How can I help you?" Dean talked quickly as if he wanted to leave the moment of being caught dancing long behind him. He held out his hand for Castiel.

Castiel shook it, replying, "I'm Castiel. My car is a couple of blocks down the road. I have a flat tire and no spare."

Dean pulled out a clipboard, "Make, model."

"Rolls Royce. Black and white. You can't miss it."

Dean whistled, "Fancy, schmancy."

Castiel replied, defensively, "It's not mine. It's my brother's."

"I don't judge." Dean walked over to a clipboard on the shop's counter. After a moment of peering at his notes for a moment, he said, "It's your lucky night. We have that tire in stock." He looked at Castiel, still dripping on the floor with his teeth chattering slightly. "I'll go get it with my tow truck. Why don't you make yourself comfortable?"

"I could go with you," Castiel replied.

"That's not necessary. You look like you are freezing. Hold on." Dean walked to the door and disappeared for a few moments. He re-emerged with a pair of jeans and a T-shirt. "Here's some dry clothes. I can't do much about the shoes because I don't think we are the same size, but this will at least warm you up some. You can change in the back office. I'll be right back with your car."

Castiel changed his clothes quickly. His leather shoes were ruined. His suit wasn't much better, but the trench coat had moderately protected his suit jacket, and his blue dress pants were covered in mud. After he was dried off, he went into the front to wait for Dean to return.

He glanced around the shop. The shop had seen better days, but it was tidy and clean. Tools lined the garage. A sign behind the counter said, "Singer and Sons." Castiel wondered if Dean's last name was Singer. He could see the mechanic owning the shop.

Dean returned to the gas station much quicker than Dean expected and deposited the Rolls in the garage. Castiel stood companionably as Dean started the work to install the tire.

So, what do you do for a living?" Dean asked, wiping his hands on a rag, before reaching over for the jack.

"I'm a lawyer," Castiel said, hoping Dean wouldn't find his profession too boring.

Dean looked surprised and impressed. "Really? That's cool. My little brother is in law school at Stanford. He’s stupid smart. What kind of law do you practice?"

Castiel smiled. "I work in personal injury law. I'm in the middle of a case right now. I was on my way back from interviewing a witness when my car broke down."

Dean raised his eyebrows. "Wow, that sounds intense. What's the case about?"

Castiel hesitated for a moment, wondering if he should share the details with a stranger. But he felt a connection with Dean and decided to open up. "A woman was killed in a fire. I think it’s due to subpar construction work. The witness I'm interviewing has some important information that could help our case."

Dean nodded, listening intently. He looked away for a few moments. Castiel wondered if had said something to upset him when Dean finally said slowly, "That's pretty interesting. It must be rewarding to help people like that."

Castiel smiled. "It can be. It's not always easy, but I feel like I'm making a difference in people's lives."

Dean nodded. "Well, I have to say, I'm impressed. I don't think I could ever be a lawyer. Too much paperwork for me. You must be brainy like Sam. I’m more blue-collar."

Castiel chuckled. "It can be a lot of paperwork, that's for sure. But it's worth it to help people get justice. I don’t think I could begin to do what you do. I’m hopeless when it comes to cars or anything mechanical."

As they continued chatting, Castiel felt comfort and ease around Dean. Dean had a friendly, easy-going quality about him that was relaxing. He didn’t feel like he needed to put on any pretenses when talking to him. Castiel worked in the family law firm, where he was always expected to have proper decorum and to choose his words carefully in a potentially explosive environment. He never could be himself. He always felt alone, even when surrounded by her supposed family. Only his brother, Jimmy, had been able to see through Castiel’s cool façade. And when his twin died twelve years previously, he felt like he lost a puzzle piece that he never quite reconnected. Castiel had adopted Jimmy’s daughter, Claire, after her parents died in a car accident, and she helped fill a large gap, but even with Claire, he had stuffed his feelings as deep as he could.

He gasped suddenly, “Claire. I need to call her.” He’d been so distracted by the car and the storm he had forgotten to check in with his daughter. He knew he was going to be home late tonight, and his assistant Meg was staying overnight, but he always checked in with her before bed. “Do you mind if I use your phone?”

Castiel saw a flicker of disappointment in Dean’s eyes as he replied, “Help yourself.” He pointed to the phone on the counter. Castiel walked across the room and dialed home. Claire picked up the phone as soon as it rang.

“Dad?” She asked urgently. “Are you ok? I was getting worried.”

He reassured her, “I’m fine. But Uncle Gabe should have replaced the tires on his car. I had a blowout, and Gabe being Gabe, didn’t have a spare.”

She asked worriedly, “Where are you at?”

“Singer and Sons Auto. The car was towed here, and I’m getting a tire replaced now. Is Meg still with you?” Castiel’s assistant, Meg, was sarcastic and funny. The rest of the firm didn’t know what to make of her, but she and Castiel had been friends in college. After Jimmy died, Castiel struggled to maintain his part of the family practice and take care of Claire. Meg dropped everything and moved in with him to help. She was part assistant, part paralegal, part nanny, but always a help. Castiel considered her his one act of true rebellion. His family didn’t appreciate Meg and her snarky way but she had always been there for him when no one else had been. She had moved into her own place a few years ago, but she still hung out with Claire when the Castiel had a late night.

“We were playing poker. I think she’s cheating again.”

“You aren’t playing her for money again, are you?”

Claire responded, “We are playing for marshmallows. She’s got almost the whole bag now. I think I have enough left for a single mug of hot cocoa."

"Well, it's the night for cocoa. Maybe you should take your winnings and retire for the evening while you still have enough. I better get back to helping Dean. “

"Drive careful, Dad."

After handing up with Claire, Castiel headed back to Dean. Dean was still working efficiently and almost finished installing the tire.

Dean asked airily, "Everything ok with your wife?"

Castiel responded, "Claire's my daughter. No wife. Or husband. Just my daughter and my dipshit brother Gabriel, who fails to keep a spare tire in his trunk. I have some other older brothers named Raphael, Luke, and Michael, and a couple of cousins but we only tolerate each other."

Dean smiled at him, "I just have the one brother. Well, it looks like we're wrapping up here. Cash or credit?" Dean headed to the cash register with Castiel on his heels.

As Castiel counted out the bills to pay for the tire, he was trying to will time to stand still. He hadn't felt as connected to a person like Dean in years. Since college really. As he returned his money to the wallet, he impulsively pulled out a picture of Claire. "This is Claire."

Dean looked at the picture, "She’s lovely. She has your eyes. I don't envy you, man. Raising a teenage daughter must be brutal."

"She started at Raymond High School early. She's really smart, but sadly she knows she is really smart. I love her, but she has her moments. Do you have kids?"

Dean jerked back, dropping the picture onto the counter. He looked uncomfortable as he responded, "I had a stepson named Ben. When things didn't work out with his mother, they moved to Wisconsin. I talk to him from time to time on the phone, but they've moved on." There was almost a wistful tone to his voice. As he turned around, his elbow hit a container of pens that scattered across the counter, rolling in different directions, and onto the floor. 

Castiel started to help him, but Dean stopped him. "It's ok, Cas. I'll finish up here. You probably should head out during this storm lull."

Feeling slightly rebuked, Castiel thanked Dean and climbed into his car. He drove off into the night.