By: Ridley

Beta: Tidia & insights from Mog!

"I don't know which blows my mind more, the fact Bobby was married or you and Sammy dared to tread where I would never go." Caleb Reaves pulled the basket of peanuts closer to him and eyed his best friend. "Desperate times call for desperate measures, I guess."

Dean grinned, paused in lifting his beer bottle to his lips. "So you never read Bobby?"

"Deuce, I'm more sadist than masochist." In truth, Caleb was more than a little afraid of what he might find, and what Bobby's retribution might be.

"It wasn't that bad." Dean put his beer down grabbed a handful of peanuts "You should have seen the house, though. Unbelievable."

"What about his wife? Did she favor Fiona?"

Dean shook his head. "No, man. She was pretty- more like Ellen. At least I think she would have been, minus the gore and hellfire in her eyes."

Caleb shuddered. "Definitely another reason to stay a bachelor."

"You're never getting hitched, Damien?"

"And deprive all the ladies of spending time with this? I may be a sadist, but I'm not heartless." Caleb lifted his hands, drawing some attention at the Handle Bar Grill.

Dean shook his head. "I'm serious, Dude."

Caleb held his gaze, picking up on the feelings beneath Dean's carefree attitude. "I can't risk it even if I wanted to."

"Because of your dad."

"And my grandfather. Let's not forget about good old Noah, who tried to send his wife and child to the afterlife in a blaze of glory. Not exactly the kind of track record that makes me New York's most eligible bachelor."

"That's not you, man."

"Doesn't mean it couldn't be." Caleb took another drink of his beer. "But what about you, Deuce? You thinking about settling down?"

"Considering the time table, I don't think so."

"Let's speak in hypotheticals." Caleb dusted salt from his hands, shoving the bowl of peanuts towards Dean once more. "If there were no expiration date looming in the distance would there be a place for a Mrs. Winchester?"

Dean picked up a couple of the nuts. "Maybe."

Caleb tilted his head, catching a glimpse of the thoughts going through the younger man's mind. "Lisa?"

"You pilfering in my head, Damien? I thought you couldn't do that anymore."

Caleb grinned. "I've figured out I can't pick up stuff that might be Guardian related. Your little dream date with Lisa is like public record-out there for the taking."

"Great. The Freedom Of Information Act applies to psychics."

"She's the hot yoga chick with your own personal mini-me, right? The Wisteria Lane wannabe who gave you a scare a few months back?"

"Yeah."

"You still think the kid could be yours?"

"For his sake let's hope not."

"Dude, you'd be a great dad."

"Yeah, because I had such an awesome role model."

Caleb frowned, picking up on the surge of anger from his friend. "It has nothing to do with Johnny. You're not like him."

"Are you sure about that?"

"Yes." Caleb made sure Dean was looking at him. "You're your own man, Dean."

"But what kind of man?"

"A good one." Caleb turned on the barstool so he could get a better look at his friend. "What's going on with you?"

Dean shrugged, glanced towards the back of the bar where Sam was talking with a blond woman and her dark-haired friend. "Just been thinking about what kind of legacy I'll be leaving behind."

Caleb let the insinuation of Dean's impending doom slide. "Something going on with Sammy?"

"Seems little brother thinks he needs to be more like me."

"This could be fun to watch." Caleb raised a brow, checked out the two women Sam was entertaining. "'bout damn time the runt loosened up."

Dean looked at him. "I don't think he sees it as a positive thing." He took a swallow of his beer. "More like a last ditch survival technique. From the good Dr. Jekyll to the evil Mr. Hyde."

Caleb didn't miss the hurt that flashed through Dean's green eyes. "Dean, there's a hell of lot worse men Sam could emulate."

Dean snorted. "Like Dad? I think I have that one covered-car, coat, music. . ."

"How did I know Johnny was going to rear his ugly head in this conversation again?"

"Everything comes back to him."

Caleb sighed, picking at the label on his beer bottle. He knew when Dean called it wasn't just to give him the bad news about Bela taking the Colt. "I'm guessing Bobby's friend Freddy Krueger didn't pull any punches when he was walking around in your head either, huh?"

Dean grabbed another handful of nuts. "Why do you think Dad did it, Caleb?"

"Did what?"

"Died for me? Took my place, went to hell." Dean raised his gaze. "Do you think it was some kind of act of atonement? Penance?"

Caleb couldn't lie. "Maybe. He had a lot to make up for." He knew it wasn't the answer Dean wanted or needed. "But I don't think that was the only reason. John was a bastard, but he was a bastard who loved his kids. And as far as I know-no good parent wants their kid to die before them."

"Could've been about Sam."

Caleb frowned. "Sam?"

"Yeah." Dean glanced towards his brother again. "I mean…maybe he thought I was the only one who could save Sammy. Maybe he knew what was going to go down with old Yellow-Eyes."

"Believe or not, Dean, not everything in Johnny's world was about Sam. The last time I checked he had two sons."

Dean gave him a `you're shitting me' look. "You sure it wasn't one son and a well-trained guard dog?"

Caleb's gut twisted at the term, one he had thrown at John on several occasions, accusing his mentor of keeping Dean on a short leash to do his bidding. "He loved you, Dean. You were his son. He just let his pain blind him to that sometimes."

"You can't even deny it." Dean shook his head, ran a hand through his hair. "I'm pathetic."

"You're not pathetic!" Caleb said, lowering his voice when a few people at the other end of the bar looked their way. He bent his head closer to Dean's. "You're the most self-sacrificing bastard I know- it's what's gotten us in this mess. You're sense of self-preservation is a little skewed, that's all."

Dean laughed. "I guess that's better than how Sammy put it."

Caleb glanced towards the youngest Winchester before pinning Dean with a hard look. "And just how did Sammy put it?"

"He said I didn't want to be saved." Dean swallowed thickly, looked down at the bar. "He asked me what was wrong with me." Dean lifted his gaze. "What the fuck is wrong with me, Damien?"

"Goddamnit, Dean." Caleb ran a hand down his mouth. "Nothing's wrong with you! Do you understand me?"

"I don't understand anything anymore. I mean I spent my whole life worshipping at the man's feet, and now all I can feel when I think about him is how screwed up he was…how he screwed me up."

"Dean, all parents screw up their kids. It's a little side effect of being human. You're no different than the rest of us. All this shit is just messing with your head, causing you to doubt yourself. It's what they want."

"Ruby said…"

"Fuck Ruby!" Caleb felt like strangling someone, for starters a blonde witch with a big mouth. "Stay away from that bony-ass bitch. Sam should have wasted her instead of the crossroads demon." If Caleb had his way, he'd end her soon enough. In the meantime he would warn Sam about putting his faith in the wrong people when his brother needed his faith reinforced.

"What if she's right?"

"She has her own damn agenda, Dean. Don't doubt that. Just like Bela helped herself to the Colt. You can bet Ruby is out to get something out of this."

"She said there was no way out of the deal. "

"And she told Sam she could help you. She's working all angles."

"What if I become one of them? You and Sam gonna hunt me down?"

Caleb sighed, fought to get his anger in check. "I get that you're scared, kiddo. Believe me. I understand that fear. Becoming what you hate the most. Becoming what you've spent your whole life hunting." He would have done anything to spare Dean that kind of torment. "But you could never be one of them. I know you. Inside and out. That kind of evil…you're not capable of."

"I've seen it happen, Caleb." Dean licked his lips. "In my dream the bastard knew things about me, was right about everything."

"That's what hell is, man. It's a freakin' fun house mirror, twisting what scares us the most. We become our own worst enemy." Caleb held Dean's gaze.

"I don't want to die, Damien."

"That's good, Deuce. Because I don't plan on letting that happen for at least another sixty years or so."

"Guys!" Sam interrupted, slinging his arm over Dean's shoulder, sloshing his beer on the bar. "I just hooked up with Shelly and her friend Kimmy."

Caleb fought to keep a grin from his face as Sam slightly swayed on his feet. "And how did you pull that off, Runt?"

"I used one of Dean's lines…" He bobbed his eyebrows. "The producer thing."

Dean shared a look with Caleb. "That's a classic. Gets them every time."

"Soooooo…" Sam nodded towards the two women. "Who wants to join me? I have a spare."

Caleb shook his head. "I think I'll pass, Sam. I was really looking forward to letting your big brother kick my ass in pool. Give his self-esteem a little boost." He gestured to his best friend. "But by all means, Deuce, don't let me hold you back."

Dean shot a glance to the girls and then to his little brother grinning like a kid who'd just won top prize at a carnival booth. "How about you take them both, Sammy?"

"Are you sure?" Sam slurred, his smile fading slightly. His voice dropped to a loud whisper. "I mean there's two of them…" He motioned toward the girls as if he thought they were much further away.

"We have faith in you, kid." Caleb slapped him on the back.

Dean nodded, giving his brother a little shove in the women's direction. "Go get'em, Tiger."

Caleb laughed when Sam shuffled away. "They are so going to eat him alive."

Dean looked at his friend. "Think I should rescue him?"

"Nah. Better he learn now just how big your shoes are to fill before he goes and buys himself a leather jacket and cuts his hair."

Dean grinned. "He could hurt himself."

"No worse than the time he tried to shave when he was seven."

"I don't want him to change because of all this shit, man." Dean narrowed his gaze. "I don't want either of you to change."

Caleb cleared his throat and glanced away. "You know me, Deuce. I'm not going to do anything stupid."

"Good. Because I do know you. Inside and out. Understand?"

"I thought I was here to cheer you up?"

"You're here to help us with Bela."

"Right. My words of wisdom on that subject are - next time, call Joshua. He would have had the dream root and you and Sammy would still have the Colt. His bitching would have been heavenly compared to the trouble it's going to be getting that gun back."

Dean shrugged. "Josh told us not to call for a while. I figured we owed him that much."

"Maybe. But this was important - it was Bobby."

Dean sighed. "Wonder if hell has a spot for a really good thief?"

Caleb raised his beer. "Great minds think a like."

"So, you ready for me to kick your ass in that game of pool, Damien?"

"Oh yeah. You can tell me more about this Lisa and what you had planned after that Norman Rockwell picnic."

"Dude," Dean groaned, "let it go."

"No way. The Reaves line may die with me, but I would so make an awesome uncle."

Dean snorted. "Like I would let my kid hang out with you."

"Hey, Johnny didn't have a problem with it. You and Sammy turned out okay."

Dean smiled, but it didn't quite reach his eyes. "But I'm not Dad, now am I?"

Caleb shook his head. "No. You're definitely not your dad."

The younger man's smile faded. "Sometimes I wonder just who the hell I am."

Caleb nudged him with his shoulder. "You're my best friend and Sammy's big brother." He lifted his fist in the air, silver ring flashing in the neon light. "Not to mention The Guardian of The Brotherhood."

Dean rolled his eyes, but bumped his fist against Caleb's. "How could I forget that? We're going to rule the world someday."

"At least the supernatural side of it."

"You're not going to give up on me, are you?" Dean picked up a pool stick.

"Nope. I expect this time next year we'll be living the high life as The Triad." Caleb fed some quarters into the table.

Dean shook his head. "At some fine drinking establishment like this?"

"Hell yeah-some things don't change."

Caleb's faith was unwavering- the good guys had to win in the end. There would be a way to fix it all, and they would find it together.

RcJ