Oliver 'Oli' Winchester, Sam Winchester's younger twin and Dean Winchester's baby brother. When their dad goes on a hunting trip and doesn't come home Oli and Dean go and get Sam from college to go find him.
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"Dean, I swear you throw one more sweet wrapper at me I'm going to kill you." Oli glares, turning to face his older brother from his motel bed. Dean grins and throws another one "Come on man. I just want to get some sleep before we head off to meet dad...When he actually calls." Oli tells him. "Okay, get some beauty sleep. You definitely need it." Dean responds. Oli grabs one of the wrapper and chucks it at Dean "Ass." he glares. "Bitch." Dean counters. Rolling his eyes Oli pulls his shirt off and climbs into bed, as he does Dean's phone beeps to show a voicemail. Oli ignores it and dozes off until Dean chucks a shirt at him "Up and dressed dad's got in contact, we need to get Sammy." he tells him. Oli groans "What'd dad say?" he asks, pulling his shirt on. "Here." Dean chucks a tape recorder at him. Frowning Oli presses play, confused when he hears their dad's voice "Dean...something big is starting to happen...I need to try and figure out what's going on. It may... Be very careful, Dean. We're all in danger." fee recording of John says, Oli pressing stop. "You run it through a gold wave?" Oli asks. "And slowed it, press play." Dean responds. Oli does so "I can never go home." a female voice says. Oli turns it off and chucks the recorder to Dean "So...why we getting Sam?" he asks. "Because we need his help to find dad." Dean tells him. "We know where he went, why not just head there now?" Oli asks. "Because we might need help." Dean responds. "Okay, fine." Oli nods, packing his stuff up. Dean sighs "I know you and Sam-" he starts. "Don't want to talk about it." Oli cuts him off. "Okay." Dean nods. Oli sighs "Sorry." he tells Dean. "It's alright Oli, I get it. Now, let's go." Dean says.
Oli sighs "We going in now? We've been here for hours." he asks. "Yeah, come on." Dean nods, climbing out the car. "Finally." Oli tells him. The two of them walk round the side of the apartment building to a window "Definitely this one?" Oli asks. "Yep." Dean nods. "After you Princess." Oli smirks. Dean rolls his head and climbs the drainage pipe, using his knife to shimmy the window open. Once Dean climbs in Oli follows him up and in, finding Dean and Sam fighting each other in the dark. Dean knocks Sam down and pins him to the floor, one hand at Sam's neck and the other holding his wrist "Whoa, easy, tiger." he smiles. "Dean?" Sam asks, breathing hard. Dean laughs "You scared the crap out of me!" Sam exclaims. "That's 'cause you're out of practice." Dean tells him. Sam grabs Dean's hand and pulls in hard, slamming his heel into Dean's back as Dean lands on the floor "Or not. Get off of me." Dean tells him, tapping Sam twice. Oli crosses arms as Sam pulls Dean up "What the hell are you doing here?" Sam asks. "Well, I was looking for a beer. Oli on the other hand was still climbing in." Dean says putting his hands on Sam's shoulders. "What the hell are you doing here?" Sam reiterates. "Okay. All right. We gotta talk." Dean tells him. "Uh, the phone?" Sam asks. "If we'd'a called, would you have picked up?" Oli asks. Sam goes to answer but stops as the light gets turned on by a blonde in short shorts and a cropped Smurfs shirt "Sam?" she asks.
The three brothers turn their heads in unison "Jess. Hey. Dean, Oli, this is my girlfriend, Jessica." Sam introduces. Dean looks her up and down "Wait, your brothers Dean and Oli?" Jess smiles making Sam nod. Dean grins and moves closer "Oh, I love the Smurfs. You know, I gotta tell you. You are completely out of my brother's league." he tells her. Oli rolls his eyes slightly at Dean's flirting "Just let me put something on." Jess says turning to go. "No, no, no, I wouldn't dream of it. Seriously. Anyway, we gotta borrow your boyfriend here, talk about some private family business. But, uh, nice meeting you." Dan tells her. "No." Sam tells him, going over to Jess and putting an arm around her "No, whatever you want to say, you can say it in front of her." he tells his brothers. "Okay. Um. Dad hasn't been home in a few days." Oli tells him. "So he's working overtime on a Miller Time shift. He'll stumble back in sooner or later." Sam responds. Dean ducks his head and looks back up "Dad's on a hunting trip. And he hasn't been home in a few days." he tells him. "Jess, excuse us. We have to go outside." Sam tells his girlfriend.
