Supernatural Imagines and Preferences

Charlie Bradbury- 2

A/N- I'M SO SORRY! THIS WAS SUPPOSED TO BE UP LAST FRIDAY BUT I WAS SO BUSY AND ;-; UGH IM SORRY

You hurriedly searched through your closet, desperate to find a decent outfit for your date. After a short while, you huffed and sat on the floor defeatedly. Sam walked in and stared at you strangely.

"[Y/N]? What's going on?" He asked, sitting down beside you.

"I'm going on a date with Charlie tonight, and I literally have nothing to wear." You mumbled, putting your face in your hands and leaning against Sam. He wrapped a comforting arm around your shoulders and chuckled.

"I may not be a fashion mogul, but if I can see correctly, you seem to have a shit ton of cute date clothes in your closet." He said quietly, a small smile on his face. You groaned.

"You're a boy, you don't understand. I have nothing cute to wear that would impress Charlie!" You exclaimed.

Sam shook his head as he ruffled your hair and stood up. He made his way to your closet and picked out a random shirt and a pair of jeans. "How about this?" He asked, holding them up.

You shook your head. "The shirt is orange, dumbass. Everyone knows that if you wear orange, it makes you look paler."

Sam scoffed and shook his head, tossing the clothes back into the closet. He then grabbed a pair of booty shorts and a crop top, offering it to you.

"Sam! I can't have her thinking I'm a slut!" You shrieked. Sam rolled his eyes and sighed as he searched through your closet more.

After several rejections and many threats to simply cancel the date, Sam pulled out a cute dress you hadn't worn in ages. It was short, yellow, and a bit lacy at the bottom. You grinned when you saw it, your eyes lighting up. Sam sighed in relief and tossed the dress to you.

Meanwhile, Dean was at Charlie's house, trying his best to get her ready.

"Dean, I'm nervous. What if I screw it up? What if she doesn't like me?" She asked, chewing on her nails. Dean smacked her hands away from her mouth.

"First of all, I don't want you chewing on your nails. It's a bad habit. Secondly, you're not gonna screw it up. You're too pretty to mess anything up. And third, if she doesn't like you, then it's her loss. You're the prettiest girl I know... But don't tell [Y/N] I said that." Dean said as he lead Charlie to the bathroom to help her fix her hair.

She grinned and followed Dean, standing in front of the mirror while Dean tried his best to work the flat iron. Charlie knew Dean wasn't exactly a make up artist, but she appreciated the effort he made.

After about twenty minutes, Dean finished getting Charlie ready and stepped back to look at his masterpiece. Charlie practically shined. She applied her makeup perfectly and thanks to Dean's effort, she didn't have a single stray hair.

She walked to the front door, a bright smile on her face. She eagerly waited for you to arrive.

When you finished changing and getting your makeup on, you hugged Sam and thanked him. He chuckled.

"You're gonna do great, [Y/N]. And if Charlie doesn't like you, well, then that's that. But that's not gonna happen." He said, leading you to the front door. "And if you have a problem...."

"Yeah, yeah, I'll call you." You said as you walked to the door. "See you in a bit!" You called over your shoulder as you left, driving to Charlie's house quickly. Sam shook his head and grinned.

When you arrived, you smoothed out your dress and did a bit of last minute touch ups before hopping out and walking up to Charlie's front door.

You rang the doorbell, and within seconds, it was swung open to reveal Charlie, grinning and positively glowing. Dean stood behind her, holding her shoulders in a paternal manner.

"[Y/N], I want you to take good care of Charlie. Because if you don't, well..." Dean gave you a menacing glare, and you giggled. He didn't intimidate you.

"Okay, Dean, I get it. Shall we?" You asked Charlie, reaching your hand out to hold hers. She accepted it, and you walked to your car, your fingers intertwined with hers.

You could tell it was the start of a beautiful relationship.