Caroline stood in the middle of the road looking around her, waiting. She prayed to anyone who was listening that she had done everything right. She had spent the whole ride back to Bobby's reading everything there was on Demons. This was her last hope to save Dean, as far as she knew, and she couldn't risk messing this up. It was the middle of the night and Caroline carefully retrieved Dean's car keys and took the Impala for a drive. Caroline was so determined that when she found herself standing in the middle of the crossroad she wasn't scared, she was completely calm.

Just as she was ready to turn around and mark this idea off as a lost cause, a man appeared in front of her. Caroline jumped in surprise as the man in front of her smiled wickedly, taking joy from her sudden fear. Caroline's calm reserve was now gone and adrenaline began coursing through her veins. Everything in her body told her to run but she just stood completely still as she tried to remember how to breathe. Caroline took a deep breath and took in the man standing in front of her. He was average height with short cut black hair, deep blue eyes, and a wicked grin across his lips. No one had to tell her this was a demon, the way he held himself said it all. The man arched an eyebrow and stepped closer to Caroline, his grin widening as he took in her fear.

"Well, what can I do for you princess?" The man said, his tone patronizing.

Caroline took another deep breath before looking the man in the eye, refusing to back down. "I want to make a deal."

The man tilted his head to the side as he stared at Caroline, his eyes now black. "Well my dear, you have come to the right place. What can I do for you?"

Caroline thought about this for a moment. What would Dean do once he found out she had made a deal with a demon? She could walk away, scratch this plan, and spend the next year with Dean, enjoying their last few moments together. It was a nice idea, but it wasn't an option for Caroline. She wasn't going to stand around and let Dean count the days down on the calendar.

Caroline inhaled a shaky breathe, trying her best to calm her nerves. She had spent the whole car ride back to town thinking this over, and even now as her fear told her to turn and run, there was no chance Caroline would back down. She wasn't a Winchester, her name wasn't that well known just yet. There was a chance she would get a good 10 years with Dean before the devil came to collect. No, this was the thing she had to do.

"I want to save Dean Winchester." Caroline said, her voice more controlled than she had planned it to be.

The demon in front of her smirked as he started to pace around the shaking blonde girl in front of him. To him, Caroline was just another love-sick child making a foolish deal to save a boy. He had made deals like this thousands of times over the centuries. Well…not quite like this deal. This time a Winchester was on the line. The demon continued to circle Caroline, enjoying the way he made her nervous. Her heartbeat was so loud he could almost feel it jumping out of her chest into his hand. Caroline simply stood there, completely still, her eyes following the demon as he circled her.

"Well, let's see," the demon began, looking Caroline up and down. "Your soul is pure, which isn't something you see too often in these parts. Why do you want to trade your soul for his?"

"I-" Caroline started then pressed her lips together nervously.

The demon stopped his circling behind Caroline. Caroline tensed as she felt his hands rest on her shoulders, his breath now beating against her neck.

"If you can't say it, why sell your soul for him?" He whispered into Caroline's ear.

Caroline took in another shaky breath. "I…love him."

The demon backed away from Caroline as his sinister laughter filled the darkness. The sound skated across Caroline's skin and sent a shiver down her spine. The demon of the crossroads now stood in front of Caroline grinning at her, amusement gleaming in his eyes. He slowly walked closer to Caroline, finally stopping a few inches from her. Caroline stopped breathing as she stared up into the man's unearthly blue eyes. She felt the blood in her veins turn to ice when he brushed his fingertips across her face. Caroline bit her bottom lip, stifling the scream that was forming in the back of her throat. The demon laughed lightly as he stared into Caroline's fear stricken face.

"My dear…I would love to make a deal with you." Without warning he backed away from Caroline and placed his hands in his pockets. "Sadly, I can't grant you your wish. He signed his soul away and no one in their right mind would let a Winchester slip through their hands."

Caroline gaped at the man as he continued to grin at her, obviously mocking her.

"I'll do anything!" Caroline shouted in desperation. "I don't need all 10 years, just please…let me save him!"

The demon walked up to Caroline once more, kissed her on the cheek and whispered "Have a lovely year. No one will let Dean Winchester live past that". In the time it took Caroline to blink the crossroad's demon had disappeared. Caroline found herself standing alone in the middle of the road again, but this time her heart was heavy and her hope was gone. Caroline placed a hand over her mouth to quiet the sob that escaped her lips. It was all too much for her, finally accepting the fact that she really only had less than a year with Dean left.

Caroline's legs gave way and she crumpled to the ground. She sat there as she cried, her chest heaving as she tried to take in enough air. She was drowning. From the hope she had just lost, the realization of how much time they had left together, the fear building inside her as she thought about what she would do after that year. It was all so much to handle, and ever since Dean had given her the bad news she pushed her feelings away. She had ignored them for as long as she could and she was now completely out of options. For the first time since this whole thing started, Caroline believed she couldn't save Dean.

Caroline pushed the kitchen door open slowly, trying to keep the door from creaking. When the door was open enough for her to fit, she kicked off her shoes, picked them off the ground, and squeezed through the small opening. Just as slowly as she had opened the door she pushed the door closed behind her with a soft click. Caroline paused for a moment to make sure no one had woken up. When she was satisfied with the silence, Caroline slowly padded across the kitchen floor. When her feet hit the carpet she released the breath she was holding, taking comfort in the idea that the carpet would muffle the sound of her feet moving across the floor.

Caroline found she had started to relax prematurely. She was two steps into the living room when suddenly the room was flooded with light from the lamp across the room. Caroline turned in surprise to find Dean sitting on the couch, his elbows resting against his knees, his eyebrows knitted together from the glare he shot her. Caroline bit her lip as her guilt started to form knots in the pit of her stomach.

"Where were you?" Dean asked, his voice cold.

Caroline turned her gaze to the carpet underneath her feet. "I just wanted to take a drive."

"Don't feed me that bullshit Caroline. Where were you?" Dean snapped.

Caroline laughed nervously as she rolled her eyes. "I couldn't sleep, I just needed some air."

Caroline looked up to gauge Dean's expression. When she looked at him she winced, his expression cold. Caroline had never seen Dean like this before. Just as she thought she knew every expression that crossed Dean Winchester's face, now he stared at her with so much anger burning in his eyes. Caroline held herself, trying to bring the warmth back to her skin. Looking at Dean like this she didn't know what to say. Caroline knew if she lied he'd see right through it and it would just feed into his anger, but telling him the truth would make his blood boil. Caroline shook her head, refusing to say anything. Dean pushed himself off the couch and walked up to Caroline, now glaring down at her. Caroline felt so small as Dean towered over her, his anger coming off of him in waves. She turned her gaze back to the carpet, too shaken to look Dean in the eye.

"You reek of sulfur." Dean snapped harshly.

Caroline swallowed the lump that formed in the back of her throat before turning her face up to Dean's. She felt herself shake under Dean's cold gaze. It was hard to stand there, being the person on the other end of that angry stare.

Caroline took a deep breath. "I…I was trying to um…I wanted to help you and-"

"What were you doing Caroline?" Dean cut her off, now looking panicked.

Caroline bit her bottom lip. "I…went to the crossroads."

Dean stared at her wide eyed for a minute, completely taken aback from her answer. So many scenarios had run through his head when he found the other side of the bed empty and his car missing, but this…he would never have guessed. Dean turned away from Caroline and began to pace back and forth in front of her, running his hand through his hair every few seconds as he shook his head. Caroline stood there silently, thinking it would be a good idea not to babble this time. After a few silent minutes Dean turned back to Caroline as he rested his hands on his hips.

"Tell me you didn't make a deal." Dean said through gritted teeth.

Caroline lowered and shook her head. "I tried but…he wouldn't take my deal."

Dean stood there watching Caroline. He wanted so badly to touch her, hold her in his arms and run his fingers through her hair. The second the words came out of her mouth relief washed over him. It was one thing for him to lose her in a year because he had a one way ticket to hell, but he didn't know if he could handle watching Caroline lose her life because of him. He couldn't lose her just to clean up his own mess. He wanted to hold her, but he fought off the urge.

"Pack your stuff Caroline, I'm taking you home."

Dean walked past her and out the back door, slamming it behind him.