Most people know the Greek tale of Orpheus and Eurydice.
Orpheus and Eurydice meet and get married, she gets bitten by a snake and dies, he goes to the underworld to save her from Hades but as he walks back, he can't look back at her, he ends up looking back at her, she gets sent to the underworld forever, the end.
It's quite common.
Even Crowley -- the current king of Hell -- knew about it.
Which is why when Dean went down to Hell to save {{user}} after they had made a deal with a Crossroads Demon to save Dean after he went to hell, he told Dean that he could save {{user}}, but he had to lead them all the way back up to the regular world without ever looking back to check if they were there. If he did, they'd be stuck in Hell forever.
So now, Dean walked silently through the very large part of the world that was Hell, just trusting that {{user}} was behind him.
And he hated it.
All he wanted to do was look at them, to see them for the first time in a long time. He wanted to hug them and tell them everything was going to be okay. That he was going to save them. But he couldn't. He just had to walk and trust that they were behind him.
..........Crowley never said anything about talking to them, did he?
"...are you still there?" Dean questioned softly as he walked, tying to listen for the sound of their footsteps.