Dean was in a lot of pain.
New Years Eve they were hunting a spirit. It was supposed to be an easy hunt. Sam didn't even come; he hung out back at the motel. But as it turns out, nothing is really that easy for the Winchesters.
John and Dean were taking turns digging up the grave of a construction worker, shot three times by his daughter. He stuck around the construction sight and caused fatal "accidents" to the other workers.
They had already hit the coffin when the ghost showed up.
It threw Dean out of the grave immediately. He hit his back on a nearby grave stone. Then it went after John.
John was flung out of the grave as well, but landed flat on his back in the grass. Before he knew it, the ghost was on top of him, digging its nails into his chest.
"You tryin' to dig me up? Tryin' to send me away?" The ghost sneered as John cried out in pain. "I shouldn't even be dead! That bitch just couldn't take me anymore! What was I supposed to do? I was trying to be a good father. Tryin' to instil some discipline. You know what I'm saying, don't ya? You understand!"
Suddenly, a shot rang out, and the ghost disappeared. John looked over to see Dean standing over him with a shotgun. He was holding his side with one hand. He nodded to the grave.
John stood, ignoring the pain in his chest. He hopped back into the grave and struck the coffin with the shovel. Meanwhile, Dean was standing guard.
John was getting the coffin open when he heard Dean scream.
Dean was flung away from the grave. He felt an invisible force dragging him away, digging into his skin. He felt blood pouring down his neck and chest. John didn't even look up from what he was doing.
John poured salt across the bones, and lit the match. As soon as the match hit the lighter fluid, the whole skeleton went up in flames. He turned just in time to see the spirit, who was on top of Dean, disappear into flames.
Once the ghost was gone, John rushed to his sons side. Dean was bleeding, badly. He was groaning, and wasn't responding to John's questioning. "Dean, can you hear me? Dean, answer me."
After a few minutes of struggling, John managed to get Dean in the back of the Impala. He called Sam and told him to get the first aid supplies ready.
"What, why? What happened? Is Dean alright?" Sam's worried tone rang over the other line.
"Just get the damn kit ready, Sam." John yelled, hanging up the phone.
When he pulled the Impala into the parking lot, Sam was already outside. He ran past John and went straight to the backseat where Dean was lying. "Oh my God! Dean!" Sam cried out.
"Shut up, Sam! We don't want to draw attention to ourselves. Help me get him inside."
They laid him down on the motel bed, and John got to work patching him up. He stripped him of his clothes except for his boxers to get a better look at the injuries.
Sam stood behind him. "Oh my God... Dad... there is blood everywhere!" Sam felt his whole body shaking. "We need to get him to a hospital or something!"
John shook his head. "No, Sam, he'll be fine. We just need to bandage him up."
"Sam you need to be quiet! I'm trying to work here."
When Dean woke up, he was understandably confused. The last thing he remembered, he was at the graveyard, being attacked by a ghost. But when he awoke, he was staring at a popcorn ceiling.
His whole body ached, and he could feel the bandages all over his skin. He knew he must have been back at the motel.
He looked over to his side, and saw Sam, asleep in a chair next to his bed. Dean sat up slowly, careful not to mess with his bandages. Even so, it still hurt to move, and he couldn't stop a hiss of pain from escaping his lips.
"Dean?" Sam stirred, and was surprised to see his brother awake. "Dean! You're awake!" Sam hopped out of his chair and sat beside Dean on the bed.
"What the hell happened, Sammy?" Dean groaned.
"You got hurt on the hunt. Dad patched you up. How are you feeling?" Sam's voice was high-pitched with worry.
"I've been worse. Where's Dad?"
Sam stared at him and shrugged. "I don't know. He took off last night once you were okay. He hasn't been back, yet."
Dean nodded. John always disappeared after bad hunts, even when Dean was badly hurt. He was used to it.
"Dean," Sam's voice was unusually quiet, now. "You need to be more careful."
Dean scoffed. "I am careful, Sammy. It's just part of the job. Sometimes you get hurt."
"I've never gotten hurt this badly. Even Dad doesn't get hurt as often as you do." Sam argued. "I'm just worried about you, Dean."
Dean smiled. "There's no reason to worry about me, kiddo. I'm fine. Just a little bruised, that's all. But it'll go away."
Sam didn't look convinced. "Dean," Sam put on his business-like face again, and Dean couldn't help but grin. It had been awhile since he had seen that face. "You know how I feel about hunting..."
"We all know how you feel about hunting, Sam. You tell us all the time."
"Dean, please. I'm being serious."
"So am I!"
"Dean!" Sam shouted, effectively shutting Dean up. "I don't want to do this anymore. I don't want to hunt. And I don't want you to, either!" He paused as if waiting for Dean to argue, but he remained silent. "You're gonna get yourself killed out there because you're always jumping into trouble! You're always trying to protect me or Dad, and you're always getting hurt because of it!"
"Let's just go!" Sam stood up. He had been thinking about this, planning it, Dean could tell. He'd wanted to have the conversation for a long time. "Let's just get out of here! Your 20, Dean! Almost 21! You and me, we can get out of this life. This hellhole. We can do it together!"
Dean didn't know what to say. "Sam, we can't just... leave! What about Dad?"
"Fuck him! He's never here anyway! We don't need him. He's always going on about protecting us, but all he's gonna do is get us killed!"
"Sam I can't just take you! That would be kidnapping!" Dean didn't know what the kid was thinking. Take off? They couldn't just take off! It reminded him of the last time Sam tried this in Flagstaff. Was he planning on running away again? This time with Dean?
"Dean, please!" Sam sat back down, taking Dean's hand. "I hate it here. I hate everything about this life. The only good thing is you." Sam's eyes were teary, but he wasn't crying. Not yet. "Let's just go."
Dean wanted to say yes. All he wanted was for Sam to be safe and happy, and this seemed like the way to go about it. But... he couldn't. He couldn't leave Dad. He'd come looking for them, and he'd definitely find the. Dad was a hunter, of course.
Dean shook his head. "I... I can't, Sammy. I just can't."
Sam sighed, letting go of Dean. He didn't look surprised. "Yeah, I know."
Sam didn't mention this conversation again, and neither did Dean. But Dean still kept an eye on him, to see if he planned on making the trip without him.
Years later, Dean would regret not saying yes.