Supernatural preferences and imagines

Castiel catch-up

Your first hunt- Castiel had saved you from a demon almost a year ago. Since then, he had brought you back to the bunker to live as the demons had killed you parents. The boys helped you become a hunter until one day Castiel appeared in the bunker. He took you to hunt a low level demon as a start to hunting down the demon who killed your parents. You managed to trick the demon into walking into a devils trap after taunting it. Cas quickly stabbed the demon with his angel blade. It was an easy hunt but you couldn't help but smile at the formal compliment he gave you afterwards.

He's impressed by you- The boys and you had been hunting a nest of vampires. The boys were taking down most of the vamps, while you were getting the people the vamps were drinking out of but hadn't turned yet. You had just released the last prisoner when you heard footsteps behind you. Pausing, you ducked and spun around as a knife slashed over your head. Stepping to the side, you kicked at the vamps stomach. It stumbled back as your foot connected with its torso. You advanced, blade in hand. You quickly cut off its head and hear more vamps behind you. Slashing and punching, you make your way through vamp after vamp. You knock the last one to the ground and cut off its head, when Cas appears calling your name, but stops when he sees you clearly have the situation covered. Smirking, you wipe off your blade and walk past him.

The next three kind of connect, so keep that in mind.

He realizes he likes you- His P.O.V.
I'd been confused for a while. Basic human customs were baffling enough, but they were nothing compared to how I felt around Y/N. She was so kind and her smile seemed to make the whole world brighter. Even the mention of her name made my heart beat faster. I'd been experiencing these things for a while now, so while Y/N was out getting groceries, I sought out Sam for some advice.
Finding him in the library, I walked to him.
"Sam, can I have some advice?"
Closing his book and setting it to the side, he looked at me expectantly, "Sure, what is it?"
I paused, not sure how to phrase what I was experiencing.
"It's about Y/N. Every time I'm around her, I get this unusual feeling in my stomach and my heart beats faster. I admire her kindness, but whenever I try to tell her, my words get all mixed up."
Sam chuckled and I tilted my head, confused, until he said, "Cas, you like her."
"I...like her?"
"Yeah, like romantically. It's pretty normal."
Sam smiled kindly at me, " Don't worry, Cas. I'm sure she likes you too, she never quits talking about you."
I smiled to myself, thinking about that possibility. I look back up at Sam.
"How do I tell her?"
Dean poked his head around the wall. " You're finally telling Y/N you like her?"
I nod, "Hopefully. I don't know much about how to do this kind of thing though."
Dean sat down next to Sam. "Well Cas, don't worry. We'll teach you everything."

First date- You'd noticed Castiel staring at you and getting flustered when you talked to him for a while before he told you he liked you, so it wasn't much of a surprise. However, your first date was full of them. He told you to dress up, so you did your makeup and hair and put on a cute red dress. He then flew you to the rooftop overlooking your favorite city. He had set up a beautiful table with flowers and fancy food. Best of all, a bottle of the best champagne. At first you both were a bit nervous and awkward, but eventually you both relaxed and talked for hours.

First kiss- Your first kiss with Cas was after your first date. You had been talking for a long time and it was late at night or early in the morning. Cas noticed you yawning.
"Y/N, are you tired?"
You smiled sheepishly, "Yeah, a bit."
Cas flew you both back to the bunker in front of your bedroom door.
Turning to him, you said, "Thank you for such a great time. I really enjoyed it."
He smiled at you. "I also had a great time."
For a couple seconds, you just stood there looking into his mesmerizing eyes. Then, almost without thinking, you pressed your lips to his. You pull away quickly, aware that he hadn't moved. You looked down embarrassed, until he tilted your chin up and this time he kissed you. Your hands were in his hair and his around your waist as your lips moved in perfect harmony. When he finally broke away, you were both breathless.
You smiled and murmured, " You had me scared there for a second."
"I'm sorry, you just surprised me. Sam and Dean said you might do that."
You chuckled, "You asked them how to date me?"
Now he was looking down embarrassed. "I'm not completely sure of the proper human ways."
You kiss him again, then smile.
"I don't know, I think you're pretty good at it."
"Dean told me to use a pick up line, but Sam was firmly against it."
"Yeah, it's probably a good thing you didn't. Deans pick up lines are pretty awful."
You paused. "But I'm pretty sure you could have said anything and I would've gone a date with you. I really like you."
Cas smiled. " He told me to ask you if it hurt when you fell from heaven."
You wince and you both laugh at the irony of the line.