A/N: This is part of a challenge I have given myself that I've decided to call Project Winchester. Basically, I'm going to write a drabble, ficlet, oneshot, chapter-fic, song-fic, tag, or missing scene to every Supernatural episode (there are 115.)
If there is one moment in any Supernatural episode that is guaranteed to make me cry, it's when Dean is saying goodbye to Sam and the clock chimes in 'No Rest for the Wicked.' It gets me every single time. So this is a drabble/drabblet about that moment.

"I won't forget you when we're not together
This is the ending
Here's my surrender"

- Hawthorne Heights, 'Where Can I Stab Myself in the Ears?'

3x16 – No Rest for the Wicked
"If We Could Pretend"

The clock chimes as Dean stares at the bold number twelve that's glaring at him like a challenge. His chest is tight; fear is pushing his blood too fast for his heart to keep up with, and it pounds with effort. He feels his game face slip as the chimes echo in a menacing dong dong dong. Sam turns back to face him, tears already making their way down his face. In an instant Dean's mask is back up, even though it's broken and damaged. Sam can see right through him. He always could.

They didn't need words, they rarely did. Or maybe at this point, it's just too hard to form words. Dean knows that if he tried to open his mouth right how, sound would get caught in his throat.

Sam's lips quiver. The tears, panic, and the desperation are milliseconds from bubbling to the surface and exploding.

I'm sorry, I tried. Please don't go.

Dean swallows hard, plastering on a smile faker than plastic.

I know you did, it's ok. It'll be alright. You'll be alright. This isn't your fault.

Ruby's talking in the background but Dean's not listening. Nothing on earth could steal these last moments from him and his brother.

It's going to be ok, Sammy.

He tries to put it all into that one expression: reassurance, apologies, acceptance, comfort, love. He tries to tell Sam without actually saying anything that they would both be okay, and that Dean wouldn't change what was about to happen for anything. Living on earth with Sam dead is like hell, so he'd rather go to actual hell and have Sam stay alive.

He tries to smile again.

It's going to be ok.

Sam's still crying and Dean can see him subtly shake his head.

'No, it's not.'