Worlds Colliding

Caleb was sitting in a coffee shop somewhere in San Francisco. He had just had a business meeting for his architectural firm and it looked like he was going to be building a new high rise this year. He was reading over his numbers and drinking coffee when he saw a girl staring at him from the next booth over. Normally, if Caleb saw a hot blonde staring at him, he would be all over it, but there was something off about this girls stare, she wasn't going to hit on him or anything, she was just staring at him in a way that made him very uncomfortable.

"Can I help you Miss?" Caleb said, he probably could have been more polite about it, but he was tired and he had stuff to do. The girl reddened and looked away for a minute before standing and walking over to Caleb.

"I don't mean to intrude but can I ask you a question?"

"Uhhh… yeah I guess. What's up sweetheart?"

"Well… I was just wondering about that ring you wearing." The blonde pointed to the silver band on Caleb's hand, the ring he had worn since he was eighteen and became an official member of the Brotherhood, but not once in all those years had anyone ever asked him about it, nobody in the outside world new what it was, and even if they did it wouldn't mean anything to them anyway.

"What does it mean?"

"Do you often come up to strangers and ask about their jewelry choices?"

"Well no… it's just my boyfriend has one just like it." Caleb quirked an eyebrow, this girl was dating someone in the Brotherhood? Most of them were lone wolves. It seemed off that one of them would be settled down in San Francisco with a girl.

"Your boyfriend wears a ring just like this one?"

"Well, he doesn't really wear it, he keeps it in a safe under the bed. I have never actually seen him put it on." Caleb swallowed, there was only two men in the Brotherhood that didn't wear a ring. One was John Winchester, the other he hadn't seen in more then 2 years.

"Is his name Sam Winchester by any chance?" The blonde's mouth dropped open, Caleb had obviously hit the nail on the head.

"So you know him?" Caleb laughed. He had known that kid for eighteen years until he took off and went to Stanford, he knew him better then most people in the world.

"Yeah, he's my nephew actually."

"I didn't know he had any family." Caleb just nodded, not surprised at all that Sam hadn't mentioned his family, yet somehow it still hurt. "Whatever I guess, I never really asked. I'm Jessica by the way, Sam's girlfriend." She held out her hand, and Caleb shook it awkwardly.

"I'm Caleb." Jessica smiled; this girl was definitely out of Sam's league. Guess some of the things Caleb and Dean had tried to teach the kid about the opposite sex had finally rubbed off.

"So is the ring some family thing?" Caleb decided that was the easiest way out so he nodded.

"Yeah, all the men in our family have one, it is kind of a right of passage."

"Why doesn't Sam wear his?" Caleb looked Jess in the eye, this was awkward, the world Sam had left behind, and the world he was now apart of were crashing into each other, and Caleb felt the need to protect Sam's secrets bubble up inside his chest.

"I dunno Jess, maybe that is something you should ask him." Jess frowned.

"Yeah I guess. Well nice to meet you anyway, hope to see you around soon, maybe come over for dinner or something sometime." Caleb smiled, but knew that would never happen, Sam didn't want them in his life anymore they had to respect that. Jess began to turn away but Caleb stopped her.

"Wait." Jess turned back towards Caleb. "Is he okay?"

"What do you mean? Of course he is."

"No I mean, is he happy?" Jess thought on that for a second.

"I think so, I mean sometimes he seems to be somewhere else. I mean he reads the paper, and he seems so sad by everything he reads, like somehow it is his fault. I know that probably sounds insane… ignore me I am rambling, he is happy." Caleb sighed, he wanted her to say that Sam's life was perfect, that he had left everything behind and wasn't looking back, but he knew he was stupid for thinking that. No matter how angry or distant Sam got, he always had a fierce loyalty to his family, and to the people they saved.

"I'm glad. I'll see you around Jess."

"I know he misses you guys." Caleb snorted.

"Five minutes ago you didn't even know he had a family." Jess smiled.

"Yeah but I know him." Caleb couldn't help but think she didn't know anything about Sam. "I see how he looks when Thanksgiving and Christmas rolls around, or when he is with my family. He missed someone, I just never knew who." Caleb didn't answer, he just wished Sam would call them, call Dean.

"I gotta go Jess, take care of Sammy for us. He deserves that." Before Jess could answer, he was gone.

Later that Night…

Sam walked into the apartment, he hated having late classes on Friday, Jess always had Friday's off, and she had gone to San Francisco to visit some old friends.

"Jess? You home?" Sam called from the doorway.

"In the kitchen!" Jess yelled back. Sam went into the kitchen, Jess was making chicken. "Dinner's almost ready, there is raspberry pie for dessert." Sam smiled and gave her a kiss.

"How did I end up with someone as amazing as you?"

"You got really lucky." Sam laughed and dropped his bags in the living room.

"How was your day babe?"

"It was great, grabbed lunch with the girls, saw some old friends, oh and I ran into someone you know too." Sam frowned, and pulled a bottle of water from the fridge.

"Oh yeah, who's that?"

"Your Uncle, Caleb?" Sam choked on the water. "You okay?"

"Uh… yeah I'm fine. How did that happen?" Jess shifted awkwardly.

"Well… I asked him about the silver ring he was wearing… and I asked what it meant because I had seen yours, and he told me that all the men in your family wore one." Sam nodded. "I didn't know you had an Uncle."

"It never came up." Jessica sighed, sometimes she felt like she didn't know anything about Sam.

"Please Sam, can't you just tell me some things about your family?" Sam sighed and sat down at the kitchen table.

"Alright, what do you want to know?" Jess was shocked; Sam was actually giving her a chance, and she wasn't going miss this opportunity.

"Okay, where are your parents?" Sam looked around the room awkwardly like he didn't know quite how to answer the question.

"Well… my mom died in a fire when I was a baby, and honestly I do not know where my dad is. I haven't talked to him in a long time." Jess suddenly felt bad.

"I am so sorry about your mom Sam." Sam smiled sadly.

"It was a long time ago, I mean I was a baby. It was harder on Dean."

"Dean? Who's Dean?"

"Dean is my brother, he is four years older then me, and he is a pain in my ass." Sam laughed. "But he is a good guy." Jess smiled.

"So is that all there is? Caleb said all of the men in your family wear that ring."

"Well honestly, our whole family is men. My mom died, Caleb's mom died. Mackland is Caleb's Dad, he is a neurosurgeon, and then there is Bobby and Pastor Jim, I am not actually related to them, but they are still family, if you know what I mean." Jessica nodded, she could understand that.

"Why don't you talk to them anymore? Don't you miss them?" Sam looked away from Jess and felt a knot in his throat.

"I miss them everyday Jess, I just… I can't be who they want me to be, and I hurt them when I left. I can't go back, and they can't live in this life with me. I can't really explain that anymore."

"Okay Sam, just one more question and then I will let this go. The whole ring thing, why don't you wear it? Just because you aren't with them doesn't mean they aren't you family." Sam smiled.

"I got that ring when I was sixteen and I have never put it on. I love them all, and they will always be my family, but that ring means something different to me then it does to them, and to be quite honest… it's a lot heavier then it looks. Lets eat dinner." Jessica could tell the conversation was closed, and she never brought it up again, but she never forgot what Caleb said to her in that coffee shop, he told he to watch out for Sam, and she would, until her dying breath.