A/N: So most of my chapters are pretty short. I'm going to be honest, I kinda like leaving you guys on cliffies. So, here you go guys.
Dean was out of the car and running to the door before Charlie could even park. As soon as she did, she was right behind him, not knowing what was coming when they walked in the door. When she walked into the living room she saw Dean hugging his little brother, who was sobbing uncontrollably, and Cas was sitting on the arm of the couch, rubbing small circles on Sam's back. Cas looked up at Charlie when she came in, and pulled her into the kitchen.
"What's going on, Cas?" Charlie asked quietly, getting the impression that it was not something that should be talked about in front of Sam, or in hearing distance.
"There was an accident." Cas said, barely over a murmur, looking over her shoulder at Dean and Sam. "Jess and her folks died in a wreck last night."
"Come again?"
"Apparently, Jess' parents took her out for the day so that Sam could go ring shopping and when they were driving back, the car's brakes failed and they ended up getting in a quite explosive accident with a semi trailer on the interstate."
"Oh my god." Charlie said, looking over her shoulder at Sam, "Poor Sammy."
The two of them made their way back to the living room, Cas going back to his spot on the arm of the couch and Charlie found a spot between the two Winchesters' legs on the floor. She leaned on Sam's knee, offering quiet support, knowing that right now, Dean was really the only one that could be able to get through to Sam.
*******************TIME WARP**********************
"Sammy, you don't have to stay for the party if you don't want to. I mean the funeral was only a couple days ago."
"Dean. I've spent the entire week inside, I want to go. Besides it's about time I've met your friends," Sam said with a small smile.
"OK, but don't say I didn't warn you."
Charlie met the guys there while everyone was setting up. "It looks nice in here, guys! So I gotta run real quick. I'll be back in 15."
"Sounds good, Charlie." Dean said, smiling.
Charlie made it across town in record time, and by the time she was on her girlfriend's step, she found she had butterflies in the pit of her stomach. She pushed them down when she saw Dorothy at the door. She was wearing a subtle vintage dress and had done a 30s style makeover on her face. "Wow, babe, you look smashing."
By the time she made it back to the Roadhouse, the party was already in full swing. She held Dorothy's hand, and finding Dean in the crowd she made her way over to her friend. However, when she got there, she was just about to turn around when Dean noticed her.
"Hey! Charlie, I want you to meet our new bartender."
"Hi there, darlin'" came an all too familiar voice.
A/N: I am so sorry for killing Jess. I'm gonna be completely honest. I don't know how I'd write her because there really wasn't enough of character development on the show for her. Don't worry though, Sammy won't be alone too long.