Episode tag to The Trap

When Sam headed to bed early, Dean and Cas weren't surprised. "I'll check in on him in a little while, make sure he's not having nightmares," he told the angel.

"Sounds good." Cas grabbed his glass and downed some of his drink. He sighed. "We'll figure out another way to get to Chuck."

"Of course we will. That fucker's going down." Dean yawned and flashed his friend a tired smile. Twelve hours in Purgatory and then rescuing Sam and Eileen had taken a lot out of him. He couldn't wait to go to bed, even as keyed up as he was right now.

Cas nodded. "We'll make sure of it," he vowed. They had suffered a loss tonight that was okay - they'd get Chuck at some point down the road.

Dean hesitated for a second. "We're good now, right?"

"Yes, we're fine now. You don't have to worry," the angel assured him.

"You're sure?"

"I'm sure. Now you're dead on your feet so please go to bed."

"I can stay here and drink with you for a little while longer." Dean yawned again and then downed another glass before pouring himself some more.

The two of them sat in (a comfortable) silence for a while longer. "Maybe we should thank Rowena for telling us to work our issues out," Cas joked.

He snorted. "She definitely helped but it was mostly Purgatory and you nearly dying on me again." Dean playfully knocked his shoulder. "Don't do that."

"I'll try not to. I don't want you or Sam to die on me either."

Dean sobered for a second. "How are you doing? I never really asked you how you were coping with Jack's death."

The lost look in the angel's eyes nearly broke him. Cas just shrugged. "I'm coping as well as can be expected. It hurts. My child is gone, and then I had to kill the demon riding his body. I miss him."

Dean put his drink down and squeezed Cas' shoulder. "I'm sorry - I know I made it worse. And I miss him too. I miss Mom." He sighed.

"How are you coping with Mary's death?" Dean hadn't brought Mary up very much in the months since her death, and Cas knew he was still grieving the loss even as they were dealing with the Chuck problem.

Dean sighed. "I miss her every day. Glad I got to truly know her." She wasn't perfect and definitely not the woman he built up in his head but like he told her before, he loved her. He was grateful for the three extra years they got to spend with each other, and was still so happy Sam had the chance to make memories with her and discover who she was.

"She loved you both so very much, Dean."

He smiled at Cas. "I know. She loved you too - considered you one of her boys."

Cas beamed right back. "That was sweet of her." He sighed and downed his drink. "I think it's time to head to bed."

Dean checked his phone. "Yeah, you're right. I want to check in on Sammy, see how he's doing after the day from hell."

The two of them stood up and then went their separate ways. Dean opened Sam's door and wasn't surprised to find his brother still wide awake. "You don't have to check on me. I'm fine, Dean." But the look of relief on Sam's face said otherwise.

"You're not fine, and you don't have to pretend to be, kid. Tell me the truth," Dean encouraged as he sat down on the bed. He flashed his brother an encouraging smirk.

Sam smiled back but it didn't reach his eyes. "I'm nowhere near okay, Dean. You really think we can beat Chuck?" He needed his hope back but it felt impossible, especially now.

He nodded. "I really think we can beat Chuck. Don't know how but we got this." He intended to do more than punch Chuck the next time they saw him, even if it didn't do shit. God needed to pay for hurting Sam.

Sam fidgeted a bit before taking the covers off him and sitting up on a pillow. "I can't fucking believe I let him get in my head - I've been tortured worse."

"You have but torture is torture, and I'm guessing he knew exactly what buttons to push?"

"Yeah. It seemed so out of character for us, you know? But I couldn't take the risk." Sam lowered his eyes and felt the guilt creeping in again.

Dean tapped his shoulder. "Hey, don't do that. I trust you and know you made the right decision. What exactly happened?" He hated digging into Sam's trauma when it was so fresh but his curiosity had gotten the best of him. And maybe it'd even help his younger brother.

Sam didn't answer at first, not wanting to dive deep into the horrors he saw, but he yawned and leaned his head against Dean's shoulder (and as expected, his brother didn't even complain), needing the comfort. "You lost hope, you know? And I told Chuck that the Dean who raised me would never do that."

Dean flushed. "Yeah? Well, you're right. Chuck can go fuck himself."

He laughed, took a deep breath, and then explained everything he saw to his older brother, having to stop a few times to regain his composure. Dean listened without judgment and didn't even interject until Sam finished. "Sammy, that shit Chuck showed you? Is out of character for us both. We wouldn't have let ourselves turn like that, make Bobby and Jody take us out."

"Are you pissed I let him into my head now?" Sam desperately hoped he wasn't.

"I'm pissed at Chuck and don't blame you at all. Again, tortured. Let it go, Sammy. Be like Elsa." Dean waited and wasn't surprised when Sam snorted. He smirked at his brother. "I'm going to go now. Call me if you need." He went to stand up but stopped when Sam grabbed onto his arm.

"Stay," Sam pleaded, his voice hitching.

Dean couldn't say no to that, even if he wanted to. "Damn it, kid, the puppy dog eyes should have stopped working on me years ago. How do you still do this to me?" But he slid up to Sam's side, pulled the covers over his brother, and lay down.

Team Free Will was truly back and functioning well again, and Chuck wouldn't know what hit him next time they ran into him. But for now, Sam was a little brother in need of comfort, and Dean needed to make sure he was okay. The three of them would be able to start over when the sun rose the next day. For now, they let themselves fall apart because they truly needed it.