Dean thought he was being slick by disappearing and crying in private but Sam and Castiel were onto him. Several days after Mary's memorial and their attempt to lock Jack in the box failed, Cas knocked on Dean's door in an attempt to have an honest conversation with him but received no answer. "He's crying in the shower again," Sam told him as he passed by.
Cas winced. "Again?" At least he hadn't driven the Impala into the woods to grieve again.
Sam nodded. He just wished his brother could open up to them but he knew how Dean handled his grief - he'd come to them when he was ready but for now, he just needed to do it alone. Like his brother, he missed his mom so much he couldn't take it but he took comfort in the fact that his parents were now together and at peace. It didn't help all that much but it at least it lessened the grief just a bit.
"We have to confront him at some point." Cas didn't want to, especially when Dean's fury radiated off him and was directed mostly towards him, but it was necessary.
"And we will but just leave him be for now."
Cas sighed. "Fine. Any luck on finding Jack?"
Sam shook his head. "Nothing's coming up but we'll find him even though he doesn't want to be."
"I hope so." Jack had been pretty pissed and took off pretty quickly after escaping and nearly destroying the bunker. They had been unable to locate him since, but at least he had stopped murdering innocent people - the three of them were keeping an eye on Bible-related killings. Cas' heart continued to break and he felt guilty every time he thought about the past few months. And they still didn't know about his deal with the Empty, which he knew he had to confess to soon.
"Good luck." Sam clapped him on the shoulder and then headed to the war room.
Cas made his way to his own bedroom and sat down, trying not think so he wouldn't drown in grief, guilt, and despair.
Dean washed his hair, his whole body shaking with sobs. He tried to keep as quiet as possible so Sam and Cas didn't hear but thankfully they weren't coming in to check on him. He wanted to be strong but his mother's second death had re-opened old wounds and the trauma from her first death was hitting him full force again. He hated it with a passion but the grief overwhelmed him every step of the way. Holding on to his anger was the only thing keeping him going, and he didn't know what he'd do if that went away. He just wanted his mom back - he missed her so much and not even the fact that she and John had reunited again helped. Turning the water off and using the towel to hide the evidence of his tears when he stepped out of the shower, Dean bolted back to his room. Luckily for him, he didn't run into Cas or his brother.
As soon as he dried off and dressed himself, Dean sat down on the bed and contemplated taking Baby into the woods again. Maybe it'd make Sam and Cas suspicious but they didn't seem to be so far so that was a point in his favor. He choked on a sob and sighed. "Mom?" he asked, his voice cracking. "If you can hear me, I just want to tell you that I'm sorry and I miss you, and hope you and Dad are happy."
None of them were okay, and Dean was just barely holding on by a thread. He was thisclose to completely falling apart. Cracking at the seams, he wished to go back to just a few weeks ago, when he was happy and still had a mom.
They had to take care of this Jack situation, and maybe (just maybe) he could finally start thinking straight again without grief hanging over his head.
Life continued to deal them a shitty hand and the Winchesters just had to shut up and deal with it, even though they all needed a break at the moment.