It’s weird to think about where all the characters were at the start of the series. Not just Sam and Dean at the first episode, or the other characters upon their first appearances. But, like, where all they were on Halloween night, 2005.
Bobby Singer was probably answering the FBI phone every ten minutes as he cooked his dinner, helping hunters out of trouble with the law on their ways to breaking All Hallow’s Eve curses. Maybe he even answered a call from Dean, telling him, no, I haven’t heard from or seen your dad. Sorry, kid.
Castiel wasn’t even on Earth, but circling somewhere far above, along with all his brothers and sisters, simply watching, and of course waiting.
Jo Harvelle might have gone to a party at her own college, trying to fit in and not be “that weird girl with the knife collection”.
Ellen would be running the Roadhouse, serving some weary hunters their beers and pretzels, missing her daughter probably but being happy she was safe at college, far from hunter life.
Ash was most likely getting some info for some hunters who were passing through the roadhouse for the night.
Meg might have been running an errand of sorts for Azazel. Some poor trucker who hadn’t listened to those warnings about hitchhikers wasn’t going to see November 1st maybe.
Ruby was in Hell, proving herself “more loyal than all those sons of bitches” probably. But let’s not think too hard on that…
Anna was in college by then, her freshman year or so. She probably went out for a beer with friends at a party on campus. (Ssh, don’t tell her father the pastor!)
Bela Talbot was probably selling a mystical object for an insane amount of cash or hosting a fake seance for some filthy rich people.
Kevin Tran went trick-or-treating with his mom. They probably walked until their feet hurt and Kevin’s bag weighed ten pounds. Maybe he went as a doctor or a werewolf. Mrs. Tran made sure no one stiffed her kid on his candy. (One piece? *scoff* take two, Kevin.)
Charlie was wearing some geeky costume to a friend’s Halloween party, trying to get with the chick in the cute nurse costume.
Lisa might have been taking Ben on one of his first real trick-or-treats. One he’d actually remember, even if he was only five. He was dressed as a serial killer or something even more cool. Not a lame ghost or Frankenstein.
Garth was probably one those hunters calling Bobby to have him back up their “I’m FBI” stories. If he wasn’t using the Texas Ranger disguise. Or maybe he wasn’t even a hunter. Maybe he was still a dentist, handing out lame toothbrushes to the kids who rang his doorbell that night. Or, just to subvert stereotypes, king-size chocolate bars.
Crowley was drowning in deals. The number of deals made on Halloween night must be ridiculous. The numbers of deals becoming due must have been ridiculous too. Imagine how many Hellhounds he had to send out!
Adam might have convinced his mom to let him go to a party that night. A friend from school’s likely. He hopefully made it back before curfew.
Chuck Shurley was at work, writing one of the early Supernatural books. Maybe even the first one.
Gabriel was probably delivering some karmic overkill justice in some small town. Halloween gives amble opportunity for mischief. He probably scared some people literally to death, or trapped someone dressed in as a vampire in a tanning bed.
John Winchester was following a lead. THE lead.
Very few of these characters had any idea what the future would hold for them. If they had some idea of how their lives would go, most of them were probably dead wrong about their assumptions. NONE of these guys would have guessed where they’d be ten years from that night (except for maybe Bela, but she had an unfair advantage in that respect).