Dean and Death

The relationship between Dean Winchester and Death is strikingly serious. They only meet when necessary. The two are not friends, but Dean is one of the few who have met Death personally.

Dean is forced to respect the horseman due his immense power. Death finds Dean extremely insignificant.

Background
Since his ascension, Dean has encountered Death, and has had numerous interactions with him. Dean himself has died and come back to life many times, avoiding Death. Death came to physical form in Abandon All Hope..., but Dean was unconscious at the time.

Season 5
"To a thing like me, a thing like you...well think about how you'd feel if a bacterium sat at your table and started to get snarky. This is one tiny planet, one tiny little solar system in a galaxy that's barely out of its diapers. I'm old, Dean, very old. So I invite you to contemplate how insignificant I find you."

- Death to Dean

Dean and Death first meet in Two Minutes to Midnight as Dean heads out to retrieve Death's ring in order to open Lucifer's Cage. Dean eventually finds Death in a pizza parlor in Chicago where a hurricane is coming in. Dean fully intends to attack Death and kill him using Death's Scythe. Death, knowing Dean is coming causes the blade to heat and Dean to drop it, before inviting him to sit at his table.

Season 6
"This is hard for you, Dean. You throw away your life because you've come to assume that it'll bounce right back into your lap. The human soul is not a rubber ball. It's vulnerable, impermanent, but stronger than you know... and more valuable than you can imagine."

- Death Dean looks for Death in Appointment In Samarra for a solution for his brother's soul problem.

Season 7
"Fried pickle chip? Best in the state.” “That easy to soothe me, you think?"

- Dean and Death

Since Castiel's godhood through all of Purgatory's souls, Dean desperately searches for a way to stop him, and initially finds nothing.