Dean
Dean eventually called you two days later. You were anxious for the call. He called and asked if you were free that night. When you said you were, he said he could pick you up. You agreed and giggled after you hung up.
The Impala's horn honked while you put on the last touches on your hair. You walked out of your house looking stunning as hell to Dean who looked just as hot. "Hey," you said. "Hey," he said. "Where you taking me?"
"Somewhere special," he said and you worried you were underdress.
He drove for nearly ten minutes as you judged his taste in music. "AC/DC? Dude, I love them," you said as you softly hummed the lyrics.
"Seriously?" Dean asked with a smile.
"Yeah, my dad used to play them all the time and I grew to love them over the years," you admitted. You stared out the window humming without noticing that he stared at you for a few moments with a smile.
"Here we are," he said, a little later.
"What is this place?" You asked. It was like a park with a small food stand, pond, playground, and field.
"A park. I liked to come here when I was younger. It always made me feel normal," he said, looking at the benches that reminded him of better times. You stared at him confused. "I,uh, didn't grow up like much kids. I moved alot. Whenever we came back to this place, I'd come here."
You nodded and he lead you to the food stand. You ordered something light to eat and ate while having a wonderful conversation discussing likes and dislikes (you guys had a lot in common in those departments). After, Dean bought you an ice cream cone. He insisted that he did not want one, but he kept giving your ice cream the eye.
"Do you want some?" You asked.
"No,no, it's your-"
"Here, have some." You ended up sharing the ice cream cone and walked around the park laughing and having a good time. So much that you didn't notice where you were going and tripped. You nearly fell on top of him, but you caught yourself so your faces were a few inches away. You smiled at each other.
Sam
You did call Sam Winchester. But it wasn't for a date. You were reserving that for later. You called him with information and went on a hunt with them. It took a while, but you finally ganked the bitch. You were right, it was a shifter. Sam and you were walking to the Impala to unload some stuff while Dean stayed back to clean the mess.
"Nice work, Y/N," Sam said.
"Thanks, Sam," you said.
"Uh, hey," he said stopping. "Do you want to go out?"
You smiled. "Sure." He waiting. "Like right now?"
"Yeah."
"Sam, no offesne, but we're dirty and sweaty, and I think you have some kind of goo on your leg." You chuckled slightly realizing that both of you were in no shape for a date.
"It doesn't matter how I look when I'm with a beautiful girl," he said, causing you to blush. "There's a movie theater just down there. You want to go?" You raised tour eyebrow and turned to see that, in fact, there was a theater just down the road.
"What the hell? Let's go," you said.
You walked to the theater as you spoke about your well done hunt. At the nearly empty theater, nobody gave you or Sam another look. Sam bought tickets and snack without any problems and soon you were in the theater. Of course, Sam had chosen a horror movie.
At first, whenever a scary scene happened, you just sucked it up and pretended you weren't scared. But after some while, you couldn't just fake it and you'd flinch and cover you face with your arms. Sam noticed and in the next horror scene, he put his arm around you. He pulled you closer and you hid in his chest. There was a scene that wasn't that particularly scary, yet you still hid. "Really?" He whispered through a chuckle. "Is this the same girl that took down a shifter all on her own just an hour ago?"
"That doll is scarier than a shifter," you said, peering out for just a second before hiding again. He just laughed silently and pulled you closer.
Cas
It was just around four when Castiel knocked on your door. Luckily for you, you were ready. You opened the door to reveal Castiel standing with a bouquet of your favorite flowers. "Hello, Y/N. Dean said it was nice to bring flowers on dates," he said.
"Did Dean chose the flowers?" You asked, as he handed you the flowers.
"No, I choose them. Y/F/F remind me of you," he said completely serious.
You smiled at him. "Let me just put these in water and then we'll go," you said before leaving to do just that.
When you returned he was still standing at the door. He was looking around curiously. The moment his eyes met yours, he straightened up and said, "Do you have a map? Because I am lost in your eyes?" Once again, he said it just as confused as before. But you found it cute. Then he did the most awkward wink ever. You really wanted to wrap your arms around him and laugh, but you didn't. All you did was wink back with a smile.
"What are we doing tonight?" You asked.
"Dean said dinner and some form of entertainment is what is expected of a date," Castiel said.
"Yes, sometimes," you agreed.
"I will take you out to eat and then to a concert."
"Okay."
Your date was interesting. No one had every taken you to Jack In The Box for a dinner date before. You didn't complain. You happily ate your hamburger and curly fries. Castiel didn't have any sense of personal space either. He sat right next to you and you could feel him. You didn't complain. You noticed he hadn't even taken a bite from his burger. "Aren't you going to eat something?" You asked.
"It, uh, doesn't taste good," he said. You stared at him confused. "The molecules," he started, but then stopped himself. "I'm not a fan of burgers."
After the burgers, you two walked a little before you said, "So entertainment?"
"Yes," he stood really close to you once again. "We're going to go see the kids at the local middle school perform. Tonight is their big concert."
"How do you know about this?" You asked.
He thought for a moment before saying, "Church."
You enjoyed yourself at the concert. The kids played fairly well at the concet and the woodwinds and brass even did a cover of Queen. Cas sat really close to you. You were really enjoying his no concept of personal space.
"Did you enjoy yourself?" He asked as he walked you home.
"Yes. It was really worth all the time I put into putting on make up." You never really put much effort into your makeup until that night.
"Why?"
"Hmm?"
"Why put on makeup?
"Uh."
"You're beautiful with or without it. You would've still looked beautiful if you hadn't worn makeup." You were at your doorstep.
"I, uh. Thanks, Castiel," you stood on your toes to kiss his cheek. He was surprised and his confused puppy face whipped out of his face to be replaced by a cute blush and a possible smile.
"Can we do this again?" Castiel asked.
"What? Kiss or go on a date?" You asked.
"Both," he admitted.
"Sure. You know where to find me when you want to go out. Goodnight, Cas."
Gabriel
The next day, the guy from the candy shop called you.
"Hello?" You asked.
"Hey, it's Gabriel," the other voice said.
"Who?"
"The charming devil from the candy shop."
"Oh! Yeah. Hi."
"Are you free tonight?"
"Yeah."
"How about I pick you up?"
"You don't know where I live."
"You could tell me."
At at exactly eight o clock, there was a knock on your door. You quickly looked at yourself in the mirror before opening the door. Gabriel stood at the door holding Y/F/C.
"Decided to being you some sweets that were as sweet as you," he said causing you to blush.
"Where are we going?" You said, closing the door behind you.
"There's a carnival," Gabriel said. "and I think a certain girl needs a stuff animal tonight." He grabbed your hand and you two set off to the carnival. He did win you a stuff animal. But, not just one. He won you a teddy bear at the ring toss. He won you a toy fishy at a tossing game. He won you a giant turtle in a shooting game. Gabriel won you a giant ducky in the high stricker ( strongman or hammer game). You were most fascinated by the duck. It was huge.
"Let's go on there," he said, pointing to the ferris wheel.
"With these?" You left hand was stuffed with stuffed animals while Gabriel carried a few others and some candy.
"We can leave them with the employee there," he said.
"I don't think they allow that," you said.
"Don't worry," he said and off you went on the ferris wheel. The employee sent you off and you leaned against Gabriel while eating a few of Y/F/C. You feed him a few and giggled when you stopped. You two were lucky enough to have stopped right on top.
"It looks beautiful," you said, looking at the carnival lights from above.
"Just like you," Gabriel said. You smiled at him and noticed he had a sort of mischievous glint in his eyes.
Lucifer
Technically, you're first date was a coffee date. You sat in the booth of your local coffee shop waiting for Lucifer. You were all wrapped in a sweater and then a coat and then a scarf. In the coffee shop, you could take off the scarf and coat, but it was still pretty cold. You couldn't wear something sexy in the cold.
When you heard someone open the door to the shop, you turned to see Lucifer. You smiled at him and he smiled back. He sat right across from you. "Have you ordered something?" He asked. You shook your head. "I'll get us something."
He came back with two coffees. "How are you not cold?" You asked. He was wearing a short sleeved shirt.
"I'm used to it," he admitted. "My brother, Micheal, and I used to love playing in the snow." You started talking about family. He told you how he had a rocky relationship with his family and you bonded over that since you have the same problem. You discussed some of the happy memories you had with your families. Halfway through your cup of coffee, you both let your conversation turn more of a whine fest. You both complained about certain people and their attributes. Lucifer didn't seem to dislike your complaning self. If anything, he really loved that side of yourself.
"We should do this again," you said as you walked out of the shop.
"Agree. How about next Tuesday at four?"
"Perfect."
"Are you going walking?"
"No, my car is parked around the corner."
"Let me walk you to your car."
"In this weather?"
"I'm use to it," he reminded you.
"Okay," you said smiling at him. You walked side by side without saying much. You raised your hand to your mouth to blow warm air into it. When you lowered your hand, Lucifer grabbed your hand.
"Can't let you get cold," he said looking at you. He pulled you closer to him and you smiled at him.
Crowley
He took you to work for nearly three weeks. The guy at the repair shop kept making excuses to not fix your car. "It needs a special kind of thing that needs to be brought from China." "I have other cars to work on." "It will be ready tomorrow." "Give me another day." "Another day." "Two more days." "How about a week?"
You were beginning to worry your car would never get fixed. You weren't complaining because you were enjoying your time with Crowley. He was handsome and not irritating like most of the guys you had dated. But you wanted your car back. And after three weeks, you were getting no where with Crowley. You were starting to wonder if he was actually flirting or just being nice.
Then, one day, he dropped you off at your place. "Thanks for the ride. Better get inside and get ready to go party at the club," you said sarcastically.
"Hold on a minute, Y/N," he said getting out of the limo. "You forgot your bag."
"Oh yeah, thanks," you said.
"Do you want to go out on a date?" Crowley asked out of the blue.
You blinked for a moment. "Yes."
"Great. Pick you up tonight at eight. Wear something fancy."
"See you tonight." You smiled at each other and you walked inside. "Yes!" You said once inside. You were actually quite excited. You took a shower and put on your makeup. That's when the bell rang and you opened the door to reveal a bag of a very expensive store. You opened it to see a beautiful dress with a note attached to it. Can't wait to see you tonight -Crowley
An hour later, you were all ready in a Y/F/C dress. You stood patiently by the door feeling like a lady. There was a knock on the door and you opened it to reveal Crowley in a black tuxedo. His usual attire really. He looked you up and down with a smirk.
"My, you look wonderful, darling," he said.
"You don't look too shabby yourself. Thank you for the dress," you said. He stretched out his hand to you and you took it. He helped you down the small steps.
"Y/F/C looks good on you," he said.
"Thank you," you said once again.
You sat across from Crowley as you discussed work. You admitted how boring it was to work in the little shop you worked at. He said how it wasn't very hard to convince people to make deals with him. You assumed he was a lawyer or something of the sort.
At the restaurant, he pulled the chair out for you. "How nice," you told him.
"I am a gentleman," he admitted.
"That I can believe," you said.
You dined an exquisite meal with Crowley. You were thoroughly amazed at the fancy restaurant. You hadn't been to be a fancy restaurant in years. Yet, there you were. Having dinner in the fanciest restaurant in the state with a handsome man who had your same taste in . . .almost everything. You both liked the same music, same drinks, and both loved to be sassy as hell. Crowley made a sassy comment to the waiter when he asked to see an I.D. for you. You looked "too young" to be drinking wine. Hell, he was right. But Crowley wasn't going to let you leave that restaurant until you tried a specific wine he'd been blabbing about.
After the amazing dinner, he took you home. "Did you like the dinner?" He asked.
"Oh, yeah," you said. "Funnest night I've had in months." The car halted to a stop. "I guess I'm home. See you Monday? Sorry, the stupid mechanic hasn't been able to fix my car."
Crowley smiled. "Oh, I think it'll be ready," he said. You raised your eyebrow and the door was opened by the driver. Your mechanic was also the driver?
"Hey! You're the-" You weren't sure what to call him but he stopped you before you could say anymore.
"Your car is ready. I'll drop it off tomorrow."
"How much do I o-"
"Taken care of, darling," Crowley said.
You were overwhelmed and confused, but not too much. Obviously Crowley had some level of power and you assumed he could easily get in touch with your mechanic. You should've felt invaded or weird out by him, but you understood his reasoning. He was stalling so he could ask you out. Or at least that's what you hoped.
"You truly are a gentleman," you said, smiling back at you.