Dean was a soldier. He had a job to do – and he did it. He held himself together and carried on. Until Chuck was defeated. Until Jack buggered off to heaven. And then it was a different story. Bit by bit, day by day, he fell apart: a downward spiral sinking him ever deeper into depression.
Sam strongly suspected it had something to do with the death of a certain angel, and now that time lay heavy on his hands, Dean was finally processing the loss. Time would heal his pain. But time passed, and nothing changed. If anything, Dean's depression grew worse; the psychic wound remained open and bleeding.
One cold December night, Sam found Dean sitting in the dark, a mostly empty glass clenched in his hand. Bloodshot eyes blinked in the sudden glare of the overhead light. Aside from that, Dean didn't react to his brother's presence. He simply sat there staring off into space: his hair uncombed, his clothing rumpled; shoulders slumped, defeat oozing from every pore.
It wasn't the first time Sam had found him this way.
It probably wouldn't be the last.
Sam sighed, took the seat across from Dean, and poured himself a shot of whiskey. He knew it was useless to offer words of comfort. He'd tried repeatedly in the past. It only made Dean stagger off to continue binge drinking in the privacy of his room. So, tonight, Sam decided to try something different. Tonight he'd sit in silence.
Tonight, they'd both mourn the loss of their friend.
And so they quietly sat there for the better part of an hour, the only sound the occasional clink of a bottle refilling a glass.
It came as a shock when Dean broke the silence: the first words he'd spoken in days.
"I've never been anyone's happiness before."
"What are you talking about, Dean?"
"Cas. That's what he told me. That the Empty would come and take him away if he knew a single moment of true happiness. And he did. And it did. And I stood there like a fool. Couldn't choke out anything but 'Don't do this, Cas.' But when did he ever listen to me?" Dean slammed his glass on the table and picked up the bottle instead. He tilted his head back, and gulped down a mouthful that brought tears to his eyes.
Sam knew the fiery liquid wasn't really the cause of the tears. They'd lost Cas many times before but, apparently, this time was different. He'd certainly never seen his brother act this way. Oh, sure, he'd seen him drunk. He'd seen him cry. He'd seen him furious and raging and self-destructive. But this... this was something new. Dean's emotions were raw, his usual barriers stripped away.
"I never told him. I didn't have the chance – no, that's not true. I had time before the Empty took him. I was just too much of a coward to speak... And then he was gone. And he didn't know. He'll never know."
"Know what, Dean?" Sam whispered, not really expecting Dean to reply. But apparently it was a night for surprise confessions.
"That I loved him. That he was my happiness too."