Supernatural Imagines/Preferences

He/She Asks You To Go On A Date

Dean-
You were in a fast food drive through when he just blurted it out. He was acting really weird throughout the day, and that explained why.

Sam-
You two were doing research for a hunt when he discreetly wrote into a book 'go on a date with me?' Then passed the book over to you. It was sweet.

Charlie-
She put a montage thingy together for you. She took screenshots of her favourite characters saying the necessary words to make 'be my hobbit and help me defeat voldemort so we can live in Moondoor together happily ever after'. A mix of fandoms? I think yes.

Gabriel-
He showed you his porn tape. But guess what? He edited the woman's face out and put yours there instead. Talk about romantic...?

Castiel-
He kept saying annoyingly cheesy pickup lines that Dean told him to use all day long. In the end, he just gave up and just said it in an overly complicated way, then went to complain to Dean that his lame lines didn't work the way he preached they would.

Crowley-
He's a classy man. He found out where you live and asked you out on a candle lit dinner(with inamorta). He may like to get bloody and messy, but he's a right gentleman. Although his stalking skills may be superior to his classiness.(sorry for the reference I couldn't help myself)

Kevin-
He ordered pizza with your favourite toppings, spelling out 'be my girlfriend?' I guess you could say it was kind of cheesy...

Lucifer-
He killed people, engraving a word on each one. When they broadcasted it in the news, you were quick to put two and two together. It was a morbid way to ask you on a date, but it worked.