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It was supposed to be easy. It was supposed to be stress free.
Then again, the universe never could make anything easy for the Winchesters, could it? Not even a simple road trip.
Going cross-country wasn’t even that bad, really. Especially not when the bulk of their formative years had been spent in the Impala’s backseat, and even more especially not when Dean was behind the wheel. He did have a tendency to drive fifteen over, one that Sam had been used to for years.
Besides, Kansas to Connecticut was hardly cross-country. More like cross-half-country, which Dean’s lead foot and a few full tanks of gas could accomplish in twenty hours instead of the GPS’ promised twenty-two.
So Sam and Dean settled in for the duration, reveling in the blessed normalcy of it all. The news article they were following up on looked to be nothing but a haunting, which Dean would ordinarily dismiss as a milk run and pass off to someone else. But this was a year of trigger happy Brits, the missing mom-to-be of Lucifer Junior, and a resurrected Mary whose skills in answering texts were severely lacking, which meant Dean found himself relieved to be facing an easy case. It felt like slipping on a pair of boots old and worn enough to be broken in just right. It was comfortable, almost homey.
It felt like a goddamn vacation.
They were coming up on the Missouri-Illinois border now, the setting sun spraying an orange glow on the pavement in front of them and the cornfields to the sides.
In the corner of his eye, Dean watched Sam close his messages app and switch back to good ol’ Google Maps. He’d been texting for almost the entire last hour, fingers flying furiously across his screen. Probably talking to Eileen.
“There’s a diner at the next exit,” Sam says, and Dean can’t decide if he’s feeling happy that food is in the near future or pissed that he has to turn down the radio volume to hold a conversation. Some songs simply deserve to be blasted as loud as possible, and Springsteen’s are certainly on that list.
Dean turns on the blinker and reluctantly slows down to take the exit, following it to a bustling rural downtown. “Is it one we’ve been to before?”
“No, it’s a local one, not a chain. It’s got four and a half stars, though.”
Dean’s about to say “nice,” when he spots a familiar silhouette standing by the bus stop they’ve nearly passed. Confusion pierces the bubble of comfort this journey has so wonderfully built up around him.
“You seeing what I’m seeing, Sammy?”
He’s not looking at his brother’s face, but Dean can practically feel the way Sam’s jaw hangs open, flapping as he’s trying to puzzle out the situation and decide what to say.
“...Yeah,” Sam manages. “Yeah, I think I am.”
Because there on the sidewalk, casting long shadows in the waning light, stands a very disheveled Castiel. He hasn’t spotted them yet, so Dean turns into the nearest parking lot and cuts the engine, hopping out of the car and crossing over to where Cas is standing.
The angel spots them before they’ve reached him, but Sam beats him to speaking.
“What are you doing here?” he asks, turning the heads of two teenagers also waiting for the bus. He quiets himself, and clarifies: “I thought you were in Ohio following a lead on Kelly Kline.”
Cas sighs, and he looks… embarrassed? That can’t be right.
“I was in Ohio,” Cas says, and now he just sounds grumpy with a side of long-suffering. “But there was an... accident, and now I’m trying to get back.”
Dean exchanges a bemused look with Sam.
“What the hell kind of accident leaves you two states west? And what happened to your truck?” Dean knows he’s getting aggressive with the questioning, but he can’t help it- he’s worried. Sue him.
“My truck is still in Ohio. It’s what I’m trying to get back to.”
“What could- oh.” Sam cuts himself off, lowering his tone to gentle sympathy. “Was it a banishing sigil?”
Cas nods.
“And it threw you this far? Are you okay?” Sam’s asking all the right questions, but Dean’s starting to see red.
“Who did this? ‘Cause if Kelly’s throwing you hundreds of miles, then-”
“No, it’s… it’s fine.” Cas waves a hand, as if the words he’s searching for are suspended in midair. “It’s nothing I’m not used to. It was just hunters. I tried to explain that I didn’t mean them any harm, but they didn’t seem to want me anywhere near their case.”
“Why didn’t you just steal another car, then?” Dean asks.
Cas shuffles his feet. “That’s what I did last time, and I see no reason to leave people without transportation if it can be avoided. And I… I like this truck.”
Sam coughs to cover a smile, and Dean shakes his head. If going back to Ohio to look for his truck is what Cas wants to do, Dean supposes there’s really nothing he can do to stop him. So he sighs, backing down before an argument can erupt.
But he can’t manage to stop himself from asking, exasperated: “Do you even have bus fare?”
Cas frowns, and the only way he could possibly look more pitiful is if the skies opened up and dumped a thunderstorm on top of him. Sam elbows Dean in the side, but doesn’t give him a chance to speak before he opens his mouth.
“Why don’t you just come with us, Cas? We’re headed to Connecticut, so we’re going through Ohio anyway. It shouldn’t be too much of a detour to get you back to your truck.” Sam says, and somehow the offer makes Castiel’s brow furrow even more.
“Are you sure?” he asks, slowly. “I don’t want to distract you from your work-”
“Of course we’re sure,” Dean says. “Family road trip. It’ll be fun.”
--
For a while, it was.
The three of them found the diner Sam’s GPS had recommended, and it made a mean burger. The waitress turned out to be studying theology, and got Cas ensnared in a ten minute conversation about it. Dean was still trying to figure out how the subject came up by the time they were finished.
They pass a mini golf place on the way to the nearest motel, complete with an artificially blue waterfall shimmering a sweet yellow glow in the illumination of the streetlights. The next thing Dean knows he’s fighting a ruthless battle with Sam for second place because Cas has secret hole-in-one-every-damn-time powers. The bastard.
He elects to refill the Impala’s gas tank tonight rather than in the morning so he can sleep in as long as possible, which is how he ends up leaning on the car watching Sam and Cas through the glass doors of the convenience store. From the looks of it, they’re having a very intense discussion about which kind of chips to buy. Dean laughs to himself. The moon is high and bright, and the air is warm and calm. He can’t remember the last time things felt this peaceful.
He forgets about the Brits. He forgets about his worries regarding Mary. For a single, shining minute, Dean thinks about how grateful he is to be alive. He’s got his brother, his best friend, his car, and miles of open road to drive with them.
He goes to sleep happy that night, for the first time in a long time.
--
The next day, his good mood is gone. They hit the road around nine in the morning, the sun totally obscured by the growing storm clouds. The roads are full of potholes, and to make matters worse, they see another familiar silhouette on the side of the highway shortly after crossing into Illinois.
“You’ve got to be kidding me,” Dean grumbles.
“Just keep driving,” Cas pipes up from the backseat, tone dagger-sharp. Dean’s inclined to agree, but Sam isn’t.
“We should probably see what he wants,” Sam’s saying, like it’s reasonable. And it probably is, to be fair, so Dean slows to a stop, grimacing as Crowley turns his hand from the hitchhiking gesture to a standstill wave, waggling his fingers.
“Hello, boys. And angel,” he greets, standing up from where he was using his briefcase as a chair on the shoulder of the empty highway.
Dean rolls down the window a crack. “Cut the crap, Crowley. What the hell do you want?”
Crowley tugs on the hem of his suit jacket and straightens his tie. “Well, this is embarrassing, and believe me I hate to be asking you, but… I need a ride.”
“You need a ride. From us.” Sam states, flatly. He’s unimpressed, as is Dean.
“You can teleport,” Dean points out. “You don’t need to take a car anywhere.”
“Ordinarily, yes. But you see, I have business to attend to in a warehouse in Indiana which happens to be quite heavily warded. I can’t teleport there, or I would. It’s much preferable to hours on the road with the three of you, but I’ll take what I can get.”
“Wait a second, why didn’t you just teleport closer to the warehouse? This is Illinois. You could have just appeared on the edge of the warding and saved yourself the need to travel in the first place,” Sam says.
“Ever the logical one, Moose,” Crowley concedes, smooth as butter. “But I sensed you were in the area and felt this would double as an opportunity for you to update me on the situation with the baby nephil. You are looking for the mother, yes?”
“What do you care? And how did you even find us?” Dean snaps.
“Well, the stench of all that toxic masculinity crammed into a gas-guzzler like this is a bit hard to miss, lad.” Crowley leans down to pick up his briefcase. “And I do have a bit of a vested interest in beings capable of ending the world, so if you wouldn’t mind unlocking the doors?”
“You can’t seriously expect us to help you carry out your nefarious business,” Cas bites. Dean can practically feel the death glare he’s shooting at the demon outside.
“It’s not nefarious, just day-to-day duties as king of Hell. Things that are necessary to keep the place operational. Demons are important to the ecosystem, you know.”
“Like cockroaches,” Cas growls.
Crowley hums. “Perhaps. We are both quite resilient and determined creatures.”
“Yeah, and you’re both things I don’t want in my goddamn car,” says Dean.
“Just let him in.”
“What?” Dean and Cas both turn to stare at Sam in shock. Sam, who’s pinching the bridge of his nose like saying those words has given him a migraine.
“Just let him in,” he reiterates. “The sooner we get going, the sooner we’ll be rid of him. Besides… what’s the worst he can do?”
“I’m touched, Sam,” Crowley says, smirking.
And just like that, Dean’s got the king of freakin’ Hades in his backseat.
--
It’s not the first time Dean’s had to drive with Cas and Crowley in the backseat, but he’s pretty sure this is the first time Sam’s had the distinct pleasure of experiencing it.
“I thought you had your own set of wheels now, choir boy,” Crowley’s saying. “What happened to your independent streak?”
“I don’t see you driving yourself anywhere,” Cas retorts.
“Guys, seriously,” Sam says, turning in his seat to cut them off.
“Not worth it, Sammy,” Dean grunts, eyes glued to the road. “They’re gonna gripe like little kids coming down from a sugar high no matter what you do.”
Shockingly (and wonderfully) that comment earns them a few minutes of peace.
--
Silence very quickly turns to tension with the four of them in one car, as it turns out, and it’s Sam who breaks it first.
“So, what’s in the briefcase?” he asks. Crowley preens under the attention, Cas rolls his eyes, and Dean tries to keep focused on counting down the miles until Indiana.
“If you must know, it’s a contract,” Crowley answers. “And there’s also a magical artifact in case the negotiation goes south. Never go anywhere without a backup plan, that’s what I always say.”
“Right, because backup plans are so very necessary for negotiations that aren’t malevolent in any way,” says Cas, in such a mocking tone that he almost doesn’t sound like himself.
“You know, I really thought we’d been making strides in our relationship recently, Cassie. Especially since I saved your life during that embarrassing business with Ramiel and the Lance of Michael,” Crowley says, and Dean can feel Cas stiffening into a ball of anger. He resolves never to mention that he finds Cas’ undying hatred for the demon ever so slightly hilarious.
“You did not save my life. You were… you were furthering your own agenda. Like you always do.” Cas is bristling in indignance now, voice dangerously low. Dean knows it's because Cas would sooner die than thank Crowley for breaking the lance. He does have a sense of dignity, after all.
Sam swipes a hand over his mouth, making Dean wonder idly if his brother is trying not to laugh. Not that Dean’s in the same boat. No way, no how.
“Sorry to say this, buddy, but he kind of did.”
Cas says “Sam,” but they all know he means to say “you were supposed to be on my side.”
Then suddenly Cas leans over and connects his fist to Crowley’s shoulder.
“Ow!” he exclaims, clutching at what’s undoubtedly a bruise forming underneath his suit.
Sam turns and openly gapes at Cas, and Dean spares as much shocked staring as he can through the rear view mirror. Not that Crowley didn’t have it coming -hell, Dean’s felt the urge about a thousand times before- but Cas usually has more restraint than that.
Cas, to his credit, is unbothered. He crosses his arms and leans back against the window.
“What?” he says. “I saw a Volkswagen Beetle on the other side of the highway. It was a ‘punch buggy.’”
Sam’s hiding another chuckle, Crowley’s sputtering, and Cas is indulging himself in a self satisfied smirk.
Dean can’t help but smile too. And he thinks that somehow, by some great miracle, this trip didn’t turn out so bad after all.
Even if Crowley sulks for the rest of the ride.