Disclaimer: Own nothing......really...nothing...

Author Note: Just fluff. I watched the first episode over the other day and thought, "What if Jess had family and she died and her boyfriend just disappeared? They would have been crushed" So here is the first chapter to the answer of my question.

The Winchesters walked into the small cafe in Palo Alto and were assaulted with the smell of rich coffee. Sam inhaled deeply and smiled as his memory drifted back to days he spent here with Jess studying or when their apartment smelled like this coffee when she would surprise Sam with his favourite cup in the morning.

Sam instinctively walked to the open booth that he used to share with the woman that would have been his wife by now. He sat down on the side of the bench that was his side and stared at her side. He ran his hand over the laminated menu that Jess had once touched. He looked back at the seat across from him and could almost see her. Her blonde hair falling over her shoulders as she laughed, her smile that always touched her eyes no matter how bad a day she was having.

"You liked this place?" Dean said as he slid into the booth and shattering the image of Jessica Moore.

"It was Jess's favourite" Sam answered dejectedly after having his brother mock Jess's place but the look on Dean's face made him easily forgiven.

A young girl wearing an apron walked over to the booth carrying a little notepad and a pen. She smiled at the brothers warmly and Dean returned the smile happily; he was glad that she chose that moment to come over and break the silence that would follow what Sam just said.

"Is there anything I can get you today?" She asked as her light brown ponytail swayed behind her head.

Dean licked his lips and her cheeks turned a shade of red.

Dean opened his mouth to give her a line when Sam interrupted, "two cappuccinos to have here, thanks"

She wrote it down in her notepad and gave Dean a smile before turned around and walking away with a skip in her step. Dean watched her walk back to the counter and shook his head with a smile.

"Now I get why you like this place Sammy" He laughed

"New waitress" Sam mumbled as he stared contently at the menu.

Dean turned to look at his younger brother but knew it was best to leave him to his thoughts for a little bit. So instead his attention went to scanning the little coffee place for girls. He spotted a group of girls a few booths down that were young, cute and happy. They were drinking coffee and flicking their hair around as they laughed and talked. There were about five of them and their laughter and happy energy was filling the air around them. A young blond that was facing Dean saw him and smiled. She started talking to her friends in a hushed voice which caused a few giggles and her friends to look behind at Dean.

The waitress came back with their coffee and Sam's attention finally snapped away from the menu. He smelt his cappuccino and noticed Dean now oblivious to the waitress smiling at him.

"Can I get you anything else? We have really good cakes or wraps"

"No thanks I'm set" Sam said as he poured one packages sugar into his coffee.

Dean just shook his head to say no. The waitress left looking slightly rejected.

"It's going to get cold Dean" Sam said while indicating Dean's coffee.

Dean snapped his attention away from whatever was behind Sam and took a sip from his coffee.

"That's fancy" he said after he swallowed and his attention quickly went back to what was behind Sam.

"Dude, what are you looking at?"

"Twenty year olds I think"

Sam sighed and just went to stirring his coffee. Dean watched the girl smile at him some more and then wave. He got up and out of the booth intent on walking over to the girls

"What are you doing?" Sam asked

"Don't interrupt me when I'm in the zone Sammy"

Dean walked off to the girls hearing Sam mutter something about jailbait. Sam didn't mind Dean walking off though; it left him with time alone in his memory.

"Can I pull up a chair?" Dean asked when he reached the booth of girls in a few steps.

"Go ahead" the blonde that waved to him moments ago said with a smile, "I'm Adrianne"

"Dean" he introduced himself as he sat on a chair he just pulled over to the table.

"So what brings you to my little cafe?"

"Your little cafe, huh?"

"We're regulars" she smirked

"Well, my brother and I were just grabbing a cup of coffee from your cafe if you don't mind"

Adrianne's friends started to look awkwardly at each other before the girl sitting next to Adrianne spoke up and said, "Well, we've got to get back to campus, nice to meet you Dean" she smiled as she slid out of the booth followed the other girls except Adrianne who was getting winks from her friends.

Sam watched a group of girls walk past him and knew that he had been dwelling on the past too much. So much so that Dean had been driven off to talk to jailbait instead of him. It had been awhile since Dean had mustered up the will to hit on some girls so Sam realised this was either a good sign or a bad one.

He decided it was a good one and smiled to himself before taking a sip of his coffee. It had been five years since he had had a cup of coffee this good. Sam focussed all of his energy into remembering the taste of this coffee; he never wanted to forget the taste again. He almost jumped when he felt the vibration in his pocket.

He pulled his phone out and answered the incoming call.



"What's up Bobby?"

"If you two idjits are finished with your walk down memory lane in California, I have a hunt for you"

Sam dutifully listened to Bobby's information as Dean brushed a loose lock of Adrianne's curly blonde hair back behind her ear. She smiled at him with her plump lips.

"What are you studying at Stanford?" Dean asked absorbed with the girl not evening noticing as his brother got out of the booth and started to make his way over to them.

"English Literature, like my sister" She answered and Dean noticed the light in her hazel eyes dim a little at the mention of her sister.

"Dean, Bobby needs us" Sam said as he reached the booth his brother was sharing with some girl that Sam didn't want to notice.

"Can it wait Sa-"

"Sam Winchester?" The girl Sam hadn't noticed breathed so quietly that the brother only just heard her.

Sam gave the young girl a weird look as Dean sent a 'what the hell, dude?' look at his younger brother.

"Yeah?" Sam fidgeted

"Do you remember me?" she asked as her eyes glazed with tears

Sam's silence answered for him

"Adrianne Moore, You and my sister..." She said softly as she stood up to look Sam in the face.

Sam remembered her...Jess's little sister. He hadn't seen her since before Jess's death five years ago. She had been a quiet fifteen year old then but now she was nearly unrecognisable except that on closer inspection she looked like Jess. Same hazel eyes, same plump lips, same nose and hair. Her skin tone was lighter though and she didn't have any of Jess's freckles that Sam loved so much.

"Adrianne, what are you doing here?" Sam blurted out after recognition flooded his brain.

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