Disclaimer: My apologies about my lack of knowledge about Jenna Marbles. I know she is a well known YouTuber. But I have seen a few of her videos on YouTube and thought she was interesting and funny. I thought I'll add her as a love interest for Dean for this story.

Jenna just finished reading her text from Sam. She was disappointed that once again Dean canceled his plans to see her. She loved him but she was fed up. She was tired of waiting. She understood he had a important job, but she wondered how long she could wait.

The day they met, that was a weird day. She was at a con where social media stars were invited to meet the fans and sign autographs. She just finished her panel and was on her way to the restroom when she felt a cold chill. The organizers had told the con participants they had a private area to relax and to wonder around freely without getting harassed by fans.

She wondered why the hallway was so cold. The air conditioner was on, but she saw cold air like she was in a freezer. Then she saw a man materialize in front of her. At first she thought it was one of those prank channels or a hidden reality show, but when the man cut her across the arm, she screamed and ran away.

She had obsessed fans before, and a few that came to her home but none have physically hurt her. She wished her ex boyfriend was here. He was big and strong. But he left her for a Del Sol beer model.

She screamed when the man appeared in front of her. Then she witnessed a iron rod going through him and he vanished. There were two men in front of her. The one holding the iron rod was gorgeous. The tall one behind him was holding a shotgun. She backed away from nervousness.

"Don't worry about us, we're here to help." The one holding the rod told her.

"Come here and stand here. Don't move from this circle. The ghost won't hurt you." The tall handsome one with the nice hair told her. Then he proceeded to make a salt circle with a bag of salt surrounding her.

"A ghost? Seriously? Fine, I'll go along with it. But my agent will want to talk to you about rights about ownership about the video." Jenna told them.

At the time she thought she was a recipient of a elaborate prank gone wrong, but that illusion was realistic. It hurt her. She was already planning suing the prank channel and the con owners for assault. But what happened next changed her whole life.

The 'ghost' came back and when it tried crossing the circl it bounced away like it was repelled. She smiled at the illusion. She couldn't wait to upload this on her channel and Igram page. She was going to make so many views, maybe a Hollywood deal for a cameo in a movie. Or even her own TV series doing a prank show. She seen some of her former colleagues that started on Youshare and went on to do bigger things.

Then when she saw one of the security guards walking down the hallway, she saw the apparition turn around and 'jump' inside him. Then when the gaurd looked at Jenna he smiled. Jenna smiled back at him. At the time she thought he was an actor. But when he drew his gun and pointed it at her she got nervous. Then he proceeded to fire it. Luckily he was grabbed by the one with the dirty blonde hair and the gun missed.

When she saw how close the bullet came to hitting her and when she saw the hole in the wall behind her, she started screaming. Then she saw the one holding the security gaurd pour salt in his hand and threw his hand over his mouth. The ghost flew out of his body.

Jenna didn't know what to think. She wanted to run, but her feet was frozen. There was footsteps behind her and it was the tall guy. He was holding a shotgun. Jenna was terrified. She had haters, even a few death threats from the totally deranged fans but none that actively tried to kill her. She closed her eyes waiting for the fatal shot that killed her. But then the one that was holding the security guard was standing in front of her.

"Miss? You need to come with us, your life is in danger."

Jenna opened her eyes."Huh? Who are you?"

He held up a badge."FBI. I'm Agent Clapton and my partner here is Agent Page. We are here investigating a case. We had reports of odd behavior in this building."

"They send Federal Agents for a odd behavior? Shouldn't the local police be here?"

"This is an on going investigation. We can't go much into details, but we had reports of people that came here that were never seen again. You may be the next target." Agent Page told her, also showing off his badge.

"Oh my god. Sure. I have to call my agent, he needs to know what's happening."

"Not now. We need to move." Agent Clapton told her.

"Okay. But will this take long? I need to get back soon, I'm due to give autographs in two hours."

They walked down the halls and into every room they go in. The two men she was with didn't say much to her but she was kinda annoyed that both seem to be whispering a lot to one another. She stopped in her tracks when she heard a noise. They were currently in a dark brick room. This room was under construction due to some scaffolding and construction tools around. The lights weren't working in here, and even with the little daylight there was, she could barely see.

"You hear that?" Agent Page asked his partner.

Agent Clapton breathed out cold air. "He's here."

Then Jenna got cold. Really cold. The last thing she remembered was the 'man' jumping into her body. She barely remembered much, but she remembered having no control of her body and her attacking the two men. She was frightened. She saw the memories of the ghost's final moments. He was a contractor for a Hollywood construction company. He was born sometime in the beginning of the 20th century. He was in this room looking over at the financial records with a oil lamp. His partner was embezzling from the company and was actively trying to frame him for theft. He was here to confront him to make him confess to the theft with his fiancee watching as a witness. She was hiding in the storage closet with a camera. When his partner walked in he was ready to show him the papers when something happened. The woman he loved walked out of the closet and walked up to 'Bert' and put her arm around him and kissed him on the lips. She looked exactly like Jenna. She felt the betrayal and heartbreak of the man who witnessed his fiancee double crossing him. Bert smiled at him then he took out a gun and shot him in the heart. The last thing he saw before he died was both of them carrying his body and putting him in the closet. The next day as a ghost, he saw Bert and another man putting up bricks where his body was and sealed him forever in that closet. He recognized the other man. He was the man at the bank who gave them the loan. They were working together. After they left, he wasn't able to move on. He was too angry. His spirit stayed in that hallway always waiting for the ones that murdered him and especially Bessie. The woman who betrayed him. He attacked anyone who dared to wonder the hallways but when he saw Jenna, he felt like he was finally ready to execute his revenge, believing she was Bessie. Then Jenna woke up and saw both of them covering her with an iron chain on the floor. She pointed to the closet that was covered with bricks and told them his remains were in there. She saw both of them pick up hammers that were on the floor and smash though the bricks. Luckily the bricks were old and were poorly constructed and came down easily. There was a skeleton inside. Jenna saw them pull out salt and gasoline and were ready to light it.

"Wait!" Jenna called out.

"What? Why?" Agent Clapton asked.

"Just listen. Please."

Jenna called out the ghost's name. "Arthur. It's okay. Its over. The people who did this to you. They were punished. They all paid the price. Both Bert and the bank officer lost everything in the stock market and both died in World War Two. Bessie drank herself to death. Bessie's biggest regret was turning her back on you. She always regretted it. She was enamored with Bert's money and charm. But when you died she was scared of Bert. He threatened to stop paying for her younger brother's treatment at the hospital if she told anyone. Her brother was eight and was sick. She felt like she didn't have a choice. Her brother lived but Bessie never stopped loving you. She died with your name on her lips. She wanted to tell her she was sorry, and it's okay if you never forgive her."

Arthur's ghost materialized in front of her. His ghost blinked a few times. Then he smiled sadly at Jenna. He attempted to touch her cheek, but didn't. He looked back at the Winchesters and nodded his head. He looked at Jenna and smiled when his ghost went up in flames. Jenna had looked at the spot were Arthur was and had a single tear going down her cheek. Later that afternoon the so-called agents told her their real names and what they did. But they asked how she knew all that. Jenna told them that it was her grandfather that told her that story. Her great aunt Bessie's biggest regret was turning her back on love. She was Jenna's age when she died.

Dean, the one with the dirty blonde hair was charming. Jenna thought he was funny and sweet. They had to leave town that night, but Jenna gave Dean her number. Despite having a few million followers on social media, she was actually shy in real life. She sent him a text with a link to a private NSFW site. It was Jenna in a old school Hollywood glamor outfit with a few inches of extra leg showing. She was slightly drunk when she sent it, but she figured she'll take that risk. She was surprised and laughed her head off when Dean sent her a pic text back with him and his brother Sam dressed up as old school gangsters with cigarettes in their mouths, with them holding fake tommy guns. She sent him a laughing emoji and a heart with a extra kiss emoji.

They exchanged emails and often talked a lot long distance since then. She ran into Dean again when she was in Boston visiting relatives. Dean was there looking for an ancient artifact in a museum. He was there looking for something to perform a magic spell. Sick of waiting for Dean to ask her out, she asked him to go for drinks. Later at some hole in a wall bar she frequented back when she was in college, she challenged Dean for a game of pool. Dean and her played for fun. Then after a few games where Dean kicked her ass, she told him to make the game interesting. Twenty dollars a ball. He accepted the challenge. Sam has warned her Dean was a shark. Jenna smiled at Sam and told him she's been practicing. She played a few games, won a few, then afterwards Dean pocketed the money she lost afterwards. Smug as hell, he told her to go back to practicing, Then he ordered a beer. Jenna then challenged Dean for another game. The stakes higher. A hundred dollars a ball, plus Jenna's Cartier tennis diamond bracelet with Dean betting his car, The '67 Impala. Before Dean can answer, Sam had pulled him away.

"Are you insane! She might be scamming you. I seen her channel, she is actually a very good pool player. Real good. She won tournaments. She is playing you."

"C'mon Sam, look at her, no way she is that good. She is just a little girl baby shark. I won many games of pool over the years. I won games in every state in the country, except Hawaii. I NEVER lost a game in one sitting. Watch me win that bracelet. We can pawn it and have enough money for the next four states."

Sam shook his head, he had a feeling they would be riding buses till they get a new ride. He was right. Jenna was younger than both of them, but she was good. Real good. Dean was looking frazzled and pissed when she got ball after ball. Even with Dean trying to distract her, she never lost her concentration. The last ball was there. The 8 ball. The ball looked impossible to hit it was surrounded by Dean's stripes. It looked like Dean was going to win if she missed it. The ball Dean needed was right in front of it. Other than the jukebox playing the bar was quiet. Every patron plus the staff were watching. Dean's car keys were on the bar plus Jenna's bracelet. There was over twelve hundred bucks on the table. Sam and one of Jenna's friends were watching over it. Jenna staring into Dean's eyes blew him a kiss. Then she angled herself in what looked like a weird pretzel position. The ball bounced around the table, then it literally was almost thisclose to touching Dean's ball. It hit the 8 ball dead on and the ball went in. The whole bar cheered. Dean just stood there white faced. Losing the money was one thing. But Baby? He looked at Jenna murderously. Jenna smiled at him and held out her hand for her money, bracelet, and new car keys.

Jenna walked out of the bar with her friend laughing. She heard footsteps behind her and smiled. She knew who that was. When she turned around Dean and Sam were standing behind her. Sam looked embarrassed an Dean looked like he was ready to commit homicide.

"My car keys. Now. Jokes over."

Jenna just stared up at him with a smirk. "Fair is fair. Winner takes all."

Dean looked like he was ready to kill her. Sam, the peacemaker tried to negotiate. "Jenna, I know you won the money fair and square, but the car is our ride. We will be stuck here without it. Please."

"No."

Sam looked bewildered. A group of guys that were standing outside smoking there tried to defend Jenna and her friend from these two older creeps. "You heard the lady. She said no."

Dean with his face red with his fist clenched was ready for a fight. Lucky for him Sam pulled him away. "It's cool. We're just leaving. C'mon Dean."

Jenna just watched them walking back towards their hotel defeated. Her friend, Mariah, asked her what to do now. Jenna was holding the keys. "Let's go for a joyride."

The next few hours were fun. They took the Impala and drove all over Boston. They had fun laughing and driving and having a good time. Mariah was asking about Dean's brother. If he was seeing anyone. Jenna had told her he was single. They had stopped at a all night convenience store and bought slushees and junk food. Tonight was a night to celebrate. After she dropped off Mariah, she went home. She wasn't surprised to see Dean standing in her uncle's driveway. She never told him where she lived, but she knew how smart and clever The Winchesters were. After driving through the gate she drove towards Dean and stopped just inches of Dean's legs. She waited for him to make the first move.

Dean had walked towards the driver's window and knocked. Jenna ever the lady, had checked the mirror, doubled checked if there was lipstick and food in her teeth, and when she was satisfied she rolled down the window.

"Yes?"

"You had your fun. But my brother was serious. This is our ride. I need this car. It was the last thing my dad gave me before he died."

"Okay."

Dean was surprised. He was expecting a argument, but Jenna just handed him the keys. She gestured him to move so she can get out.

"I was waiting for you to make the first move, since you didn't I had to take the inventive. I like you Dean. I like you a lot. I want you to ask me out. I want to see what's underneath those flannel layers you wear."

Then Jenna pulled his head down so she could kiss him. The next few weeks were a blur. Since Jenna was self employed, she was free to do what she wanted. She had came along with Sam and Dean on their hunts. They had warned her it was dangerous, but Jenna said she wasn't worried. If she could get possessed by a ghost, win a cool car and take a ride with two wanted criminals, she was set. She used the trip for a travel log for her followers but was very vague on the details. Her subscribers loved it. She gained a couple thousand new followers. Since she was riding with them she helped finance the trip. She and Dean had also fooled around in the back seat.

She found herself falling in love with him. Dean must have felt the same way. After the summer ended and when Dean dropped her off in her condo in LA, he told her he really liked her, but warned her his relationships never worked out due to his job. Jenna didn't care. She told him to visit anytime. Or she could see him. Dean was hesitant, but the tug in his heart told her this relationship was special. He kissed her long and hard and promised to be with her no matter what.

So for the next two years it was special. She met Sam's girlfriend Piper and her sisters later that year and liked them immediately. She was surprised that magic existed, not to mention Heaven, Hell, The Underworld, Angels, Demons, Witches, and many other supernatural creatures and worlds existed. When she found out God existed she was floored. But sad when she found out that God was killing everything. She accepted the possibility there could be a end, but she hoped Sam and Dean and their friends saved the world. When she met Jack, Satan's son of all things, she was glad he was actually a sweet kid. He was nothing like his father, but more like his uncles. Archangels. Her religious grandparents would be pissed that everything they believed wasn't true. Michael, Gabriel, Raphael. Awesome guys. She wasn't a fan of Raphael, but liked Gabriel. He was hilarious. Michael was polite, but Jenna thought he needed to loosen up. Jack's father, Lucifer, she wasn't sure what to think of him. She didn't hate him, but she wondered about him. There must have been something about him, since Jack loved him.

She was standing on her balcony. She was waiting for a proposal, since Dean recently bought a house. She loved LA, but she was getting tired of the superficial fakeness of the people who lived here. She loved the town, Lawrence, Kansas, where Dean and Sam lived. It was a nice town. It had the city feel, but it had that hometown feeling. She knew Sam was planning to propose to Piper, since Paige accidentally spilled the beans. But since Phoebe had that vision about God, Sam's plans were shelved. She hoped Phoebe got better soon. She had a dreadful feeling that she was in great danger.

She gave Dean one last chance. If he flakes out on her again one more time it was over.