Howdy all! This is going to be a few chapters about a crazy little date Jessie and Cas went on! This is before they got married, I hope it's pretty funny! ENJOY!

Getting Ready

Jessie fished through her clothes once more hoping something new and pretty would appear. The motel room was covered in rejected outfits barely any carpet visible. Castiel had asked her out, since they never really went on a real date before. Plus it would be one of the few times her father and uncle's eyes wouldn't be glued on the pair.

"This might look nice." She said to herself as she held a red top in front of herself and looked in the mirror. After a moment though she threw it into the rest of the pile. Jessie grumbled looking around some more. Cas was going to get her in an hour and she didn't even shower yet. He was next door getting ready.

"He is probably already done. There is no way he is having this much trouble." She said as she walked into the bathroom.

"For the LAST time BLUE!" Dean said annoyed to Cas. Castiel held a red tie in one hand and a blue tie in the other. He couldn't decide which would be better so he kept asking Dean's opinion.

"Are you sure? She likes strawberries maybe she'll prefer the red." Cas said to Dean who closed his eyes and sighed ready to erupt.

"I need a drink." Dean said simply getting up and grabbing a beer. Dean narrowed his eyes at Sam who sat snickering to himself.

"Cas why don't you just ask Sam. Also you should talk to him about your shoes Sam LOVES that stuff don't ya Sammy?' Dean said smirking. Sam's eyes grew wide.

"Really?" Cas asked him.

"Well I, uh not-

"Because I never really thought about that. Which looks nice the brown or the black? Or perhaps I should acquire a tan shoe. And on the matter of the ties blue or red? I believe she likes blue berries more then strawberries. Will that make quite a difference?" Castiel flooded him with questions. Sam looked at Dean will murder in his eyes.

An hour finally passed and Castiel knocked on Jessie's door holding a bouquet of roses. The door began to open.

"Hi-wow." He said as he took her in. Jessie looked lovely in a white dress that reached her knee ,it had short lace sleeves as well. She self-consciously looked down at herself.

"Do I look weird or something?"

"No, no, no, no ,no please. You're the most beautiful girl I have ever seen." He said making her eyes grow soft with affection.

"Aren't you sweet?" She said cupping his hand. She hadn't even noticed Sam and Dean in the doorway of their room.

"Flowers." Dean said trying to cover it up with a cough. Cas snapped back to reality and handed her the roses.

'Awwww thanks." She said putting them on the dresser next to the door.

"I like your tie." Jessie said. Castiel turned to Sam.

"Thank you Sam." He said making Jessie raise an eyebrow.

"I guess we should be going." She said taking his hand. But her father put up a hand stopping them.

"Woah! Two things before you go. One I want you home by 1. Got it?" Dean told them sternly.

"Of course Dean."

"Yes daddy. What is the other thing?" She asked. Dean bit his lip looking unsure about something but tried to push it back.

"Here. If you damage her I swear I'll murder you." Dean said tossing Cas the keys to the Impala.

Everyone's eyes grew wide with astonishment.

"Dean….are you…sure?" Sam asked.

"Well you know I gave Cas a couple lessons, and I figure Jessie must get tired of zapping everywhere so… I can be selfless for tonight." He said.

"Daddy are you okay?" Jessie put her arm around her father who looked about ready to cry.

"Just go." He said. Jessie and Castiel headed to the Impala and drove off.

Hope you liked it! Guess what? I sent the cast valentines back in Feburary and I got an autograph from Jensen in the mail! They are the nicest people ever! I love the show even more.