This is Rated M for everyone!
This starts in 5.04 "The End"
Nina Dobrev as Jacquelin "Jackie" Hank (25 years old in 2014)
Dean sighs as he answers the phone, knowing it's from Castiel.
"We're talking about the Colt, right? I mean, as in the Colt?" Dean asked, looking out the window to see the praying man gone.
"We are," Castiel said on the phone.
"Well, that doesn't make any sense. I mean, why would the demons keep a gun around that, uh, kills demons?" Dean shut the drapes and plopped down on his bed, relaxing against the pillows.
"What? What? Did—I didn't—I didn't get that."
Dean laughs afterwards, finding humor in talking to an angel on a cell phone. "You know, it's kind of funny. Talking to a messenger of God on a cellphone. It's, you know, like watching a Hell's Angel ride a moped."
"This isn't funny, Dean. The voice says I'm almost out of minutes."
"Okay, all right. I'm—I'm telling you, Cas, the mooks have melted down the gun by now."
"Well, I hear differently. And if it's true and if you are still set on the insane task of killing the devil, this is how we do it. But first I have to look into this other solution."
"Wait, what other solution? And why haven't I heard this before?" Dean asked, sitting up for a moment.
"There's a woman I've heard that has a part of an angel with her. But I'm narrowing-"
"Part angel? Like Anna?" Dean asked, baffled as he gets a notebook.
"No. Her mother was human and her father was half angel and half human, but both were killed two decades ago by angels. Because nephilims are against the law in Heaven. But I have reason to believe that the child made it and is living in either secret or oblivious of what she is."
"Well, I think we should find her rather than a colt that's probably not even there." Dean lied back down, trying to erase the possibilities of finding the woman yet. He wanted to relax and sleep, rather than go on and on about someone that probably is dead.
"Where are you?"
Dean leans across the bed to grab his room key off the bedside table and says, "Kansas City, Century Hotel, room 113."
"I'll be there immediately."
"Whoa, whoa, whoa, whoa. No, no, come on, man. I just drove like sixteen hours straight, okay? I'm human. And there's stuff I got to do."
"What stuff?"
"Eat, for example. In this case, sleep. I just need like four hours once in a while, okay?" Dean began, before telling the angel he can pop in tomorrow and hangs up before falling asleep, feeling exhausted.
OCTOBER 15TH, 2014
Dean sighs as he walks in the camp, hoping to investigate further on what happens in this year since future him won't talk really and being really ominous. He stops when a beautiful and attractive young woman, with an oval face, light olive complexion, doe-eyes, and long wavy dark brown hair, walks up to him. He immediately smiles at her, giving her his flirty smile, before she rolls her eyes. "Dean, we aren't going to have sex right now. Specially since I'm pissed at you, again," She says, her strong voice echoing in his mind. "You're not supposed to scare the ten year old's, but give them a warning. Not tell them the croats are going to rip them to shreds if they don't behave."
"Oh. Uh, sorry," Dean said, feeling weird as this woman gives him a soft smile.
"Come on, I got a surprise for you," She says and yanks him down for a passionate kiss. Dean feels weird as he does, not understanding what's happening as she's not like a starving woman for him. It was sweet and he would never admit it, the kiss gave him butterflies. She pulls away with a frown after a bit and narrows her eyes at him. "Except you're not him. Not now, at least..." She begins to trail off, confusing Dean as she takes a big step back.
"Uh... sorry?" Dean says, feeling a little flustered at this woman as she raises an eyebrow at him. "Look, do you know where Cas is? I-"
"He can't help you with what you want. He's completely human now."
"What? What do you mean?" Dean asks and she sighs before looking around for her Dean, knowing he was going to be pissed at her later for this.
"Come follow me. I can kind of help. Cas is in one of his orgies right now," She says and grabs his hand, frowning at the sparks they both feel. Dean looks around as she drags him through camp, but he ends up watching people smiling at her as they walk, wondering who is this woman that seems to be with him in the future. They stop upon a small cabin and she closes the door behind them. "I'm Jackie, by the way. What year are you from?" She asks and Dean sighs as he sits down on a brown couch.
"2009 in the beginning of October," He says as she chuckles.
"You haven't met me yet then. But you will in two-four weeks," Jackie says, smiling at him as she sits across from him, dragging a chair and sitting down.
"Are we...?"
"Together? Yeah. We've been together for a long time, but I never met Sam. Even though you talk about him a lot," She says, getting out a grabbing a beer from a cooler, giving one to Dean.
"How did we meet?" Dean asked, wondering more about his future.
"You saved my life from an angel and well, let's just say I had a crush on you from the start," Jackie jokes, letting out a small laugh with Dean, who shares a laugh.
"Where's Sam?"
"Dead. Five years ago, he died," She said, letting out a frown as she remembered something deeply upsetting and even a bit disturbing for her, which Dean notices amongst his sadness.
"What?" He asked, wanting to know as tears were in her eyes.
"You used to tell me if it wasn't for me and Cas, that you wouldn't be here. That you would of killed yourself. You were trying to be romantic but it really wasn't," She said, rubbing her eye. "Don't worry, you stopped after I punched you."
"Damn... I'm sorry," He says, wondering why she's stuck around for so long. Then, they hear a shot fire off and immediately Jackie stood up and grabbed her gun from her waist, walking outside, but not before pushing Dean back in.
"They can't be seeing two Dean's around." He nods his head, but looks out the window as he sees a dead soldier and future him standing there with his gun out. But he sees Jackie run up to future him and the two hug, making him furrow his eyebrows at remembering how future him only seems happy in secret around Jackie. The two seem to be whispering to one another, but Dean knew it must be about him as they kept looking over at the cabin he was in. The two walked together, sticking to each other's side as they talked, making Dean raise his eyebrows when he saw himself tug her behind a wall and he could barely see them share a loving and passionate kiss. It felt weird to him to see future him be so... hard and cold, but super soft at the same time to one person. He watched as they just silently shared a small moment as they rested their foreheads together, both looking at each other in the eyes with tears in them.
Then, they stopped as they pulled away and began walking towards the cabin again. Dean quickly moved back to the couch before the could see him and not long after, future Dean walked in, followed by Jackie. "So you decided to roam around and mess with my girl?" Future him said, before rolling his eyes and waving his present self off as Jackie rolled her eyes. "Whatever. I don't care."
"Look, I'm sorry. It's just been a really wacky weekend," Dean said, running a hand through his spiked hair as Jackie just chuckles at him.
"Tell me about it," Future Dean says, looking over at his girl before she tosses him a beer bottle. He catches it as Jackie does the same to past Dean, who caught it and looked at Jackie who stood next to future him. All three of them began to drink before Jackie asks, "How did the mission go?" Future Dean looks between them and sighs as past Dean eyebrows furrowed.
"What was the mission, anyway?" Dean asked, crossing his arms over his chest. Future Dean smirks as he pulls a gun out of his pocket. Jackie's eyes widen as Dean's did to.
"You found it!"
"The Colt?" Dean asked himself, who reassured them both. "Where was it?"
"Everywhere," Jackie said before Future Dean continued, "They've been moving it around. Took me five years, but...I finally got it. And tonight—tonight, I'm gonna kill the devil."
"So, that's it? That's the Colt?" Risa asked, arms folded as she looked at the gun Jackie was holding before she put it on the table and moving to stand by future Dean.
"If anything can kill Lucifer, this is it," Future Dean said, pointing to the gun as past him looked over at himself to detect anything fishy going on.
"Great. Have we got anything that can find Lucifer?" Risa asked, looking over at her friend and past Dean.
"We don't have to find Lucifer. We know where he is. The demon that we caught last week, he was one of the big guy's entourage. He knew," Future Dean said, looking down at Jackie, who was hugging herself and looking uncomfortable.
"So, a demon tells you where Satan's gonna be, and you just believe it?" Risa says.
"Oh, trust me, he wasn't lying."
"And you know this how?" Risa demanded, making past Dean look over to see Jackie hugging herself.
"Our fearless leader, I'm afraid, is all too well schooled in the art of getting to the truth," Castiel said, looking sadly at Jackie, who grimaced as future Dean subtly grabbed her hand. Past Dean noticed that future him looked worried for a moment before it clicked in his mind.
"Torture? Oh, so, we're—we're torturing again," Dean said to future him, frowning before rolling his eyes in disbelief as he looks at himself. "No, that's—that's good. Classy." Castiel let out a laugh, making Jackie glare at him as future Dean did the same.
"What? I like past you," Cas defended himself as Jackie rolled her eyes.
"Lucifer is here. Now. I know the block," Dean said, looking around at the group.
"And I know the building," Jackie said, finally talking, eyebrows furrowing as she looked over to see past Dean looking at her with a soft look that only her current Dean does. Jackie shook her head before pointing down at a map, right in the middle of a hot zone.
"Oh, good—it's right in the middle of a hot zone." Castiel couldn't keep his mouth shut.
"Crawling with Croats, yeah. You saying my plan is reckless?" Dean asked, smirking at Cas.
"Are you saying we, uh, walk in straight up the driveway, past all the demons and the Croats, and we shoot the devil?"
"Yes," Jackie says, looking unhinged for a moment before calming down when future Dean caressed her hand.
"Okay, if you don't like, uh, 'reckless', I could use 'insouciant', maybe."
"Are you coming?" Dean demanded of his friend.
Castiel sighs before saying, "Of course. But why is he? I mean, he's you five years ago. If something happens to him, you're gone, right?"
"He's coming."
"Okay. Well, uh. I'll get the grunts moving."
"We're loaded and on the road by midnight."
"All righty." Castiel and Risa leave with Jackie in tow, leaving the two Deans alone for a moment.
"Why are you taking me?" Dean asked, eyebrows furrowing as he stood up from his chair.
Reloading his gun, future him shrugged as he said, "Relax. You'll be fine. Zach's looking after you, right?"
"No, that's not what I mean. I want to know what's going on," Dean said, looking over at the door.
Future him, pissed says, turning around to face his past self, "Yeah, okay. You're coming because I want you to see something. I want you to see our brother."
"Sam? I thought he was dead. That's what Jackie-"
"Jackie likes to protect me... Gosh," He rolled his eyes as he said in disbelief, "Even past me. But, anyway, Sam didn't die in Detroit. He said 'yes'."
"'Yes'?" Dean asked, wanting to know more before a long pause ensured. "Wait. You mean—"
"That's right. The big 'yes'. To the devil. Lucifer's wearing him to the prom," Dean snapped, glaring at himself.
"Why would he do that?"
"Wish I knew. But now we don't have a choice. It's in him, and it's not getting out. And we've got to kill him, Dean. And you need to see it—the whole damn thing, how bad it gets—so you can do it different." Future Dean set his gun down as he looked over the map.
"What do you mean?"
"Zach said he was gonna bring you back, right? To oh-nine?"
"Yeah."
"Well, when you get back home—you say 'yes'. You hear me? Say 'yes' to Michael."
"So, you're really from oh-nine?" Chuck asks, watching Dean with some curiosity as the hunter shrugged his shoulders.
"Yeah, afraid so." Dean looked over to see future Dean and Jackie sharing another intimate moment. Jackie sniffed, tears flowing down her eyes as she hugs future him, who also has tears in his eyes. Dean, ignores Chuck as he watches, feeling weird to see such a cold blooded him be so... vulnerable still with her. But when they pull away, she starts talking and he heard bits of "I'm going too" and how future him refused. Then, he heard that he can't risk their baby-"Wait, baby?" Dean whispered, feeling dread wash over him at the news.
"You okay there, Dean?" Chuck asked, before looking over at the arguing couple. He chuckles before telling Dean, "Must be weird seeing a future you and Jackie? No matter what happens you'll meet her."
"What?" Dean asked, but Chuck just pushed him into a van. Before they drive off.