Catching Up
Chapter 19 – Shadow

Dean read the show's description in a way too cheerful voice, "While investigating a mysterious death in Chicago, Sam and Dean run into Meg, who is thrilled to see Sam again."

All the while he refused to make eye contact with Mary who lifted a brow, "Alright Dean, we'll talk at dinner." Dean gulped and said nothing. Inside, Mary's gut churned at the thought of her son being in Hell and she couldn't help blaming herself for bringing this into their lives. Sam and Dean on the other hand were trying to figure out a way to tell Cas that Meg had died. They knew they really should have told him from the get-go and breaking the news now was sure to cause all kinds of problems. In the meantime, they tried to focus on the show's opening. A young woman was walking when her music cut out and she is chased by the shadow (roll credits) of something. She runs to her apartment and makes it in, turning on her house alarm and locking the door. Unfortunately, the shadow followed her and kills her instantly.

"Now that is a new one for me," Mary frowned. "Demon?"

"Yes and no," Sam tilted his hand side to side. "This is one those you have to watch to understand."

"What is 'Our Town'?" Cas asked in response to TV!Dean's complaint about having to dress up for the investigation.

"It's a play," Dean explained. "Kind of depressing, about the lives and deaths of these townspeople. Sammy here was…oh come on…" Dean snapped his fingers to try to remember, "What was the milkman's name?"

"Howie Newsome," Sam filled in dryly.

"That's the one," Dean grinned. "You would not believe the outfit they stuck him in. Boy I wish we had a camera back in those days."

Perhaps I can oblige, recreate the magic. Besides, I've always had a thing for milkmen. "Let's just get back the show," Sam said extremely pointedly. Spoilsport.

Onscreen, the TV!Winchesters met with the victim's landlady to learn more about the murder. She insisted everything was perfect, only that the young girl had been killed where she stood. TV!Dean had spoken to an officer who had revealed to him that the victim's heart was missing but it couldn't be a werewolf or any physical creature given the lack of evidence. TV!Dean finds a symbol in the blood on the ground but TV!Sam can't find anything related to it and there was no suspicious signs leading up to the girl's death or to the man who died before her. "I feel like I should know this," Mary pursed her lips to the side.

"Thought you said this was a new one for you," Dean said.

"Not hunt-wise, the lore, that symbol," Mary tapped her head.

"It will come to you," Dean shrugged. "For now, let's just watch Sam make puppy dog eyes at a demon."

"I didn't know that at the time," Sam protested. "You're just mad she bit your head off the first time you met."

"That was in line with Meg's attitude," Cas said. "But she's different now."

Oh man, he's remembering her taking care of him in the asylum. Now even I feel bad for the guy. "Perfect," Sam's jaw clenched. In the show, TV!Sam is suspicious of seeing Meg again and send TV!Dean to do research while he keeps on her. Meg's identity ends up checking out but TV!Dean is able find out that the symbol is a sign for a deva, demonic entity that have to be summoned and controlled at great risk.

"That's it," Mary clapped. "My father thought he'd come across a deva once, turned out to be an extremely powerful poltergeist but I helped do the research."

"Seriously mom, these would have made kick-ass bedtime stories," Dean threw out there. Meanwhile, TV!Sam was watching Meg get changed and got called a pervert by a passerby causing to Dean to cackle. "Left that out of the story baby brother."

Sammy hasn't anyone told you that's impolite? "Can it," Sam shot back acidly. "As you can see, I wasn't trying to get laid and I was right to follow her." Onscreen, TV!Sam tailed Meg to an abandoned warehouse where she has an alter set up and that familiar, to them, silver bowl with which she was speaking to someone who is apparently on their way. TV!Dean for his part discovers the victims were both born in Lawrence and they decide to call in John for back up.

Danger, Will Robinson, DANGER! "Yeah thanks," Sam rolled his eyes.

In the show, TV!Dean and TV!Sam discuss life after the hunt and the elder Winchester's wish for them to be the way they used to be. "We honestly thought it would be over after killing that damn demon," Dean took a long swig of beer.

"I'm just impressed that both of us at least thought that we had something to go back to," Sam snorted softly. Mary listened to them with overwhelming guilt and shame and heartbreak. Sam used to believe in so much and all Dean wanted was to have his family back.

She bowed her head, "I'm so sorry boys."

"We survived," Sam told her gently.

"Yeah," Dean concurred. "One hel – heck of a ride though."

The TV!Winchesters follow Meg back to the building but Meg gets the upper hand and has the deva knock them out. Meg reveals that this was really a trap for John and she's knows he's in town. She provokes Sam about their mother and Jess before trying to come on to him right in front of TV!Dean.

You sure know how to pick 'em kiddo. "Are you really going to question my decisions?" Perhaps not.

TV!Sam is able to break free and destroys the alter causing the devas to attack Meg instead, sending her out the window. "Well that plan flew out the window," Dean imitated a horrible Austrian accent.

"I swear to Chuck if you start with those stupid Arnie one-liners, I will off you myself," Sam swore.

"The moment was begging for it, anyway we got company." He jerked chin towards the screen as the boys found John in their hotel room. The family share a moment and TV!Sam and John make amends, Mary felt genuine warmth that at least something good came of this but that was before a deva attacked and it is revealed that Meg is still alive.

"We cannot catch a break," Sam said heavily.

"Especially not back then," Dean added. The TV!Winchesters manage to escape but Dean convinces them that they have to split up. They go their separate ways but Meg is still on them.

"Meg was a formidable opponent," Cas commented. "We should probably consider it fortunate that circumstance made her an ally."

Dean cleared his throat, "Yeah, tough as nails that one."

"That was the best you could come up with," Sam whispered.

"Until we figure a way to tell the truth, yes," Dean retorted. He turned to Cas, "Here buddy, you get the next episode going." He tossed the angel the remote and the DVD case.