After high school ended and Castiel didn't go to homecoming dance, the Winchesters were still hunting.
Sam went to Stanford for a few years but left it completely after his girlfriend was killed. John had died to the same demon that killed Mary and Jessica Moore.
Sam and Dean were the ones left. When Dean was 28 (a/n idk how accurate that is being as I've only watched a few episodes from season 1-3), it was speculated he was near death.
This speculation finally came true after a year. Dean had been driving back to their motel when a drunk driver collided with him, both getting scratched up and becoming unconscious.
None of them woke up early enough to call 911 and it was a back road so there wasn't anybody coming down to help them or anything. They just sat there in their cars unconscious until a stranger came to Dean, rescuing him from his wreck.
The stranger carried Dean all the way to his home and onto his couch before getting the medical kit from his bathroom to bandage his wounds.
Thankfully there was just dings and scratches, only two places that needed those sticky, paper wound closers (a/n idk what they're called). The rest just needed some alcohol cleaning and bandages.
After a few hours, Dean finally awoke. He felt something damp on his forehead and after a moment realized it was a wet rag. He swallowed, his throat feeling scratchy.
The owner of the house was sitting quietly in his arm chair and looked up when Dean woke up. "How are you feeling?" was all the person said.
"Peachy." Dean sarcastically replied in a raspy voice coughing. The person got up and got him a glass of water. Dean hesitantly took the glass and sat up to take a sip.
Clearing his throat, he spoke up normally. "Why'd you save me from the wreck? I was 'destined'," He put air quotes, "to die."
"Because, to watch an old friend would be pain inducing in the heart." The stranger replied, a tad bit of sadness in his tone.
Dean finally looked at his eyes, noticing the color, and realizing who it was.
"Cas?" "Hello, Dean" Castiel replied with a small smile on his face.