"Where would I wear that?" the brunette mumbled to herself. Annie's head tilted to the side as she observed the mannequin propped in the window. Beautiful dress. Expensive. But she never went anywhere. Blue little cocktail dress. Her favorite color too. A girl can dream, she thought to herself, giving the display one last look. She enjoyed her days off, but truthfully, she would like to be working. A part of her had hoped that the two guys from the night before would stop in again. They certainly gave her something to look at, especially since most of their clientele where either old or teenagers. Peeling herself from the storefront, Annie continued her walk. She had no place to go, but it was nice being out and about. When she walked past the liquor store, she ended up stopping. The car sitting out front was eye-catching. Annie knew anything about cars, but this one was a beauty. A black 1960 something. That's all she could tell you. Her dad would have loved this. She stepped closer look at some of the details. She wasn't the only one a couple of older guys stopped admiring the beauty just like she was before going on their way.

"You like it?"

The male's voice startled her. Annie turned frantically to the male who just stepped out of the liquor store. It was him. "This is your car?" Of course, it was. He was handsome, mysterious, and the total package. Dean nodded proudly at his Impala. That was his baby after the wall.

"She sure is." He replied while walking towards the Impala. Dean leaned into the passenger seat window setting his paper bag down on the back seat. A little refreshment run; for him and Sammy. Honestly, he was happy to run into her on the street. It seemed less creepy then going to her work every day to look at her as if it was some spectator sport, which was what he was going to do; despite what Sam thought, talking to women while sober was much different than when you were sitting at the bar half in the bag.

Annie slowly nodded. She felt a bit embarrassed, staring at his car like that. She shouldn't have felt that way, but that was just how she was. There wasn't much conversation after that. They both stood there, staring at Baby. Dean took a moment to steal a glance at the brunette standing next to him. There was a gentleness to her. He didn't know her, but she was not like most of the women he had run around with, fast and loose. No, she was different, but a good different.

"Do you want to go for a ride?" breaking one of his cardinal rules. Dean couldn't believe he even suggested it; the words left his lips so quickly.

"No, I don't think so." She sounded as shocked as Dean probably felt. "No offense, but I don't make it a habit of getting in strange men's cars." Yeah, he was cute, but she wasn't stupid. She watched the dateline.

"That's fair," Dean added. Turning on his heel, the hunter leaned up against his car. He wanted to get to know her and ready to pull out all his tricks. "My names Dean." He greeted. "You're Annie. I'm Dean. Now we're not strangers." Yup. He was about ready to kick his own-ass.

"I don't know." She was contemplating. The brunette tucked a strand of hair behind her ear as her brows furrowed in thought. It was a cool car.

"I promise you, I won't do anything weird. All these people will see you get in. I don't get to show her off that often. I'm harmless." Okay, he needed to reel it back in because he sounded desperate. Annie stayed quiet. It was uncertain what she was going to say; the girl had a mad poker face. Her brown eyes scanned the black beauty before her. What was the worst thing that could happen? Getting murdered and thrown in a ditch, but she wasn't getting creepy vibes from him. Another moment passed before her gaze fell on the male."Okay." she finally responded with a soft smile.

"Really? I mean awesome." That was easier than expected. But suddenly, the realization of a stranger taking a joy ride hit him. A sudden panic rushed through the hunter. Dean moved to the driver's side door, and a vision of very object that he and Sam moved through the vehicle flashed through his mind.

"Are you okay? You look worried. If it's not okay I don't need-"

"What? No, everything's fine. Let's do this!" fuck you anxiety, we cleaned the Impala yesterday.

Annie took her place in the passenger seat, the spot usually reserved for Sam. From Dean's perspective, the view just got a Hell of a lot better. The brunette's eyes darted this way and that, taking in the interior of the Impala. She liked the color, and it was much cleaner then she expected. Her head turned away from Dean as she locked in her seat belt. The hunter, sneaking in glances before she turned to look at him.

"Hey, missing something? Seat belt. Click it or ticket buster."

"You got it, boss." A little smirk escaped his lips. This girl was something else. She was adorable. "Around the block?"

"How fast does this go?" ignoring his question. The hunter gave her a cheeky grin before looking forward, revving the engine. The hunter let his arm hang loosely out the window. They speed off with the engine roaring.

It was freeing for Annie. She wasn't the adventurous type; rarely did she step out of her comfort zone. For example, riding in the car of a strange guy, though, he wasn't a stranger anymore. He was Dean, and Dean had been a perfect gentleman. The duo had gone to the outskirts of town, allowing Dean more freedom to show off Baby. The best part for him wasn't the fact that he had a cute girl in the front seat with him. It was seeing her enjoy herself. It was enjoyable for him too going on first impressions. Dean had a hunch that she didn't do much for herself; Annie was quiet, maybe a bit sheltered. He didn't expect anything from her, but the company was a nice change. Two people, trying to have a little fun. She didn't know him. He didn't know her. They both were working with a clean slate.

"So, Annie. Care to tell me about yourself?" Dean asked casually. After their joy ride, the two pulled up in front of the parking lot of the liquor store. It had been nearly two hours, but it felt so much shorter for the waitress. It was fun.

"There isn't that much to tell. I'm not very exciting."

"Everyone has a story." Dean genuinely wanted to know. His green eyes watched the brunette with curiosity. It was she was mulling the question over.

"Do you want to know?" she finally spoke, clearly hesitant about offering up any details of her life.

"Yeah. I want to know. You show me yours, I'll show you mine." Dean teased. However, it didn't sound as humorous out loud as it did in his head.

"I—look. My life has just been a series of things that have happened to me. Things just don't work out the way they should for me and that's okay. I never left North Dakota. Always wanted to but never found the right time. My mom ran away with the mailman. His name is Jerry, they live in Florida. My dad was a construction worker. They married young, had me young. My mom wanted more out of life then he could give her. I don't think she wanted kids and I'm also certain I'm named after one of her ex-boyfriends' sister so…" there came a pause. Her brows furrowed together as her eyes drifted out the window, staring up at the neon sign hanging above the liquor store. " I'm sorry. I don't know why I'm sharing all this."

"Don't be. I want to know."

"Um. I was in school for a while. I wanted to be a nurse. But my dad got sick, so I had to drop out, so I could take care of him. That's how I started waitressing. Randy, the owner was pretty good friends with my dad. Eh, dad died 2 years ago from lung cancer. Now I just work. Those bills won't pay themselves."

"You could have lied and told me some bullshit story. You didn't. You were honest with me when you didn't have to be. I'm glad you told me."

"What's your story? You and your friend from here?" she asked with a smile. It was his turn to be put on the spot.

"No. We're just visiting for a bit. That other guy is my brother. His name is Sam. We're staying over at The Ambassador across from the diner. We lived here once for a short while a long time ago. I don't remember it much honestly. We travel a lot, doing odd jobs here and there." Dean wiped his mouth as he thought. He wasn't lying to her, but not completely honest either. It was leaving him feeling guilty. But he sure as hell wasn't about to tell her the real reason they were in town.

"Oh? How long are you going to be here?" she should have known. He was the most exciting thing to roll into this town in a long time.

"Not sure. Depends. I might find a reason to stay." Dean answered with a soft grin. That was a flirtation if Annie ever saw one. Yes definitely. Annie had to look away as she felt her cheeks get hot.

"Okay. Well, Dean. Its been fun but I need to be getting home." She smiled warmly at her new friend before attempting to get out of the car.

"Hold on. I'll take you home. You don't need to walk." The hunter offered. The last thing he wanted was something happening to her. Given the reason for them being there in the first place, she was a prime target.

The drive to Annie's was only a 10-minute commute. They pulled up to a small yellow house with white shutters. No doubt, the home she shared with her dad. The place was secure in a quiet neighborhood with a quaint little yard.

"This is me." She sighed. "Thank you for the ride."

"Not a problem." Dean nodded. "Hey!" he called out as she started walking away. "Do you have a last name?" Dean asked playfully. Mostly he was stalling. He wasn't ready for her to walk away.

"Let's leave it at Annie." She smiled.

"Any chance I can see you again just Annie?" there he went with that cheeky grin of his.

"I work tomorrow morning. You can catch me there." She told Dean as she leaned in through the window, so she wasn't yelling across the lawn.

"I was thinking more like a date."

She should have said no. That was her first mistake. "My shift ends at 4 o'clock. You can pick me up at 6." Not even skipping a beat. Annie smiled sweetly. "Good night." She told him once again before walking away once again.

"Hey!"

"What!?" a soft chuckle escaped her lips as she turned her body to look at him.

"Nothing. I just like looking at you." He knew how to put on the charm. He watched the young woman cover her blushing cheeks in embarrassment. Turning on her heel Annie lift a hand waving behind her as the hunter revved the engine.

"Go home Dean!" she teased. If she didn't go inside, they would be doing this all night.