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Disclaimer: All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author. The author is in no way associated with the owners, creators, or producers of any media franchise. No copyright infringement is intended.

Crossover: Sleepy Hollow/Supernatural

Characters: Jennifer Mills, Sam Winchester. Side: Abbie Mills and Dean Winchester.

I enjoy these two fandoms and want to explore their relationships to one another. I think it'd be interesting :)

Author's Chapter Notes:

I'm not sure if this is a thing ANYWHERE else, but has anyone from both the Supernatural or the Sleepy Hollow fandoms thought about the Mills sisters and the Winchester brothers? Whether that be friendship, team-work or otherwise? Cas and Crane would even be fun to wite. Come on guys!! 


In all seriousness, this was born from Jenny being gorgeous and Sam being the kind of guy that would recognize it. :) I know it's corny, but I like it.


Title from Hozier's Work Song.


Context: The Mills sisters are on duty with the Winchesters to take down their respective knights of Hell. Follows Season 9 of SPN and Season 1 of SH.

Warnings: Crossover, Slightly off-cannon.

Disclaimer: All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author. The author is in no way associated with the owners, creators, or producers of any media franchise. No copyright infringement is intended.

This wasn't them; laughing, smiling, happy. This couldn't be them.

They were the broken types. The ones always fighting. The grunts.

Sitting in a bar and laughing at corny jokes? Being genuine in a person's presence, no guards and no strings? Unheard of.

If you knew Sam Winchester and Jenny Mills, you'd be thinking the same thing.

So it was only natural that this was the mantra going through Sam's mind after a few hours in Jenny's presence. Neither of them had been big talkers upon their meeting. They were the ones who studied; who read and brought information to the table. That's what they'd been doing, actually, before Jenny suggested that they both have a well-deserved drink and drove in silence to a bar.

The lighting was low. The music had a lot of base. Nobody was there. Sam, for the first time in a long time, felt a little awkward. Because the last woman he'd been in a bar with had been Amelia. And though that wound was healing, it would still go raw if poked at enough.

And he didn't want to poke it, so he tried ignoring it.

Sam noticed that they had been standing by the entrance a while, and upon looking to Jenny, he was met with intense hazel, "bar or table?"

"Bar", he cleared his throat, gesturing for her to go ahead of him. Her eyebrow reached that perfect arch he'd grown accustomed to over the past few weeks, and they walked over to the bar. He ordered a beer. She ordered a scotch. Now it was his turn to raise an eyebrow. But she looked at him square in the eye. He smiled, shaking his head. She wasn't laughing. He cleared his throat again, "just—didn't expect that." She was wordless still, but backed down a bit. Sam looked at his beer.

They were usually like this, he noticed; all silent communication and eye contact. They'd been like that in the beginning, and Sam wasn't surprised it hadn't changed. The Mills trusted on a professional level, which Sam sensed wasn't enough for both he and his brother and them. But Sam had no idea how to reach these two women. They were protective; of one another and themselves. The Mills sisters were never rude, however, they never treated the entrance of the brother's into their lives like most women, frankly, had; like saviors. Or heroes. They treated them like partners on a mission. Sam felt pressure-less—but wanted to see more of who they were. The Winchesters had always been candid to a degree; they learned that from never knowing how to keep their business as their own. But these two, were unreadable.

Jenny sipped silently while Sam tried to frantically adapt to the unreadable situation. Her eyes never left her drink. His eyes wouldn't stop darting over to her. And time wasn't even moving. "You alright, Winchester?" Her smile surprised him, but he kept cool, like she had, the whole freaking time. "Yeah—why wouldn't I be?"

"You haven't stopped looking at me since we left the bunker this morning."

"Well, you haven't really spoken since we left the bunker this morning."

Her brows scrunched, and she looked at him, "I didn't think this casual, Winchester; we have work to do."

"I'm sorry", Sam shook his head, "we can keep it professional."

"Oh, wait", her body language, again, surprises him. But he can't tell if it's genuine or sarcastic; unreadable, "don't tell me I've hurt your feelings."

Now it's his turn to scrunch his eyebrows, push and pull, "hurt my feelings?"

"Why else would you say that 'keep it professional' crap?" she drinks. Maybe she's being genuine. Her smile's too disarming. Then again, so is his when he's conning people.

Or maybe he's reading too much into this. So he smiles, too, "you didn't seem to be in a talking mood. So I'll adapt."

"Seems like you're good at that", she takes another sip; when did he get readable?

His smile stays, but now his brain calculates, "you really know how to read someone, don't you?"

"It's a skill I've acquired, yes", she polished the drink and orders another. Sam looks down, smiling still. Not only is he being read like some of the Gallic texts they were studying, he's also a drink behind Ms. Mills.

Her smile hasn't left, and they're eyes are completely challenging while they stay silent, drink, and stare.

Then she laughs, "what even is this?" she looks at him again. He smiles too. Because he's being silly and so is she; why are they playing around? He takes another drink, "how about we change topics?"

"Go for it", her smile seems permanently etched into her face. Sam likes it.

"How long you been traveling? You know a hell of a lot for, what, 25?" he finishes the drink, orders another. She's almost done with number two.

Jenny's still grinning, "25?"

Sam's still grinning, "Are you younger? People are gonna look at me funny."

And she laughs, genuine this time. And they remain like that; laughing and drinking and talking about her past and his past (as much as each will allow). And they flirt. A lot. And they sing along to the music as their drinks pile up. And Sam realizes that if he drives Dean's car in these conditions, his brother will probably kill him. So he sends him a drunken s.o.s and hopes he doesn't panic.

"By the way, your brother is a babe. An ass, but a hot one". She's completely disarmed. But to be fair, so is he; they've fallen over themselves and each other a few times and she won't stop laughing at the moose story, nor he at the bounty hunter that she nearly shot for pulling her hair.

Sam's face crunches, hiding the acute jealousy, "he is not."

She laughs again, "I'd hope you wouldn't think so."

Now he's laughing, "well, you're sister is gorgeous…like", he nods, thinking about Abigail Mills and Jenny hits his chest, "that's my sister!"

"And that's my brother", they keep laughing at each other and she nearly falls off the bench, but Sam catches her by the forearms. And she's till laughing. And her breath is warm against her face and he lifts her closer. She looks up at him, the smile still ghosting her face, "yeah, but I don't really want to kiss your brother".

Sam smiles again, and his eyes train on her lips. This woman has digressed him to the feelings of a twenty-something in college with a girl he might be falling in love with and…

He's sobering and his head is swimming; can't he have a good time without remembering, for once?

"Maybe when you're sober?" He lifts her again, but she's the one who closes the gap this time, "no time like the present, Sam Winchester."

But he has to stop her. Because he doesn't know what's going to happen if he doesn't and he's afraid that if he lets this happen that he'll open up boxes that she's been blowing the lids off of since they started all this. But he doesn't want to stop her. Because he likes Jenny Mills' smile. And she can read people better than he can. And she's better at Gallic than he is. And she wants to kiss him. And he wants to kiss her.



She's still smiling up at him a hand on each of his thighs, and he's still staring right back at her. Dean and Abbie exchange looks of slight confusion, before each go to their respective sibling.

Dean's got a hold on Sam's shoulders.

Abbie's got both hands on Jenny's sides and is putting her arms over her shoulder. Neither of their younger siblings acknowledge them, but keep on looking at each other. Abbie and Dean are going to their respective cars, and buckling them in, and they're wordless. They both look at each other, shaking heads and shrugging.

Next Morning:

"My head!"

"Why does it feel like someone hit me with a truck?"

Their entrances into the kitchen that morning had an already lively bunker silent and smiling. Sam looked at Jenny. Jenny looked at Sam. Both of them sprouted a headache.

Dean grins into his coffee cup, "If we would have been any later to pick you two up you would have".

Abbie, Jenny, and Sam give him the bitch face and he feels accomplished.

"I think I'm gonna go shower—"

"I need a shower—"

"Wow, guys. Keep something to yourself." Dean's grin is permanent.

"Shut up"; Sam and Jenny.

Dean can't stop smiling.

Abbie's shaking her head and handing both of them coffee mugs, "go—you both smell like a liquor store."

"Thanks Abbie", Sam smiles weakly. He feels like a liquor store.

"I know you are but what am I?" Jenny grins at her sister.

They collide in the door way. Sam hadn't realized how tall she was. Jenny wasn't aware of how broad he was. And after two failed attempts and a doubled over Dean, she made him go first.

"Well well well. And they thought it was going to be us", Dean laughed into his coffee mug again.

Abbie's loud laugh surprised him. And it went on too long.

She kept laughing after seeing the look of offence on Dean's face.

Chapter End Notes:

Thanks all for reading!

I hope you've enjoyed this! I'll probably start a whole drabble section about these guys because they're perfect:)

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Disclaimer: All publicly recognizable characters, settings, etc. are the property of their respective owners. The original characters and plot are the property of the author. The author is in no way associated with the owners, creators, or producers of any media franchise. No copyright infringement is intended.