Dean:
You knew he wasn't the kind of guy to come right out and ask a girl on a date mostly because he does one night stands and not relationships. But there was still a part of you that hoped he would ask you out on a date. It took a long time but after a year of flirting and hunting he finally asked you.
"So Y/N, I was wondering if you would like to maybe go on a date with me." He asked you after a hunt where you both almost died.
"Why this sudden change of heart?" You asked him while he was stitching up a pretty big gash on your shoulder.
"Well, I've liked you for a while now and I never really knew how to ask because I've never been in a relationship before and I want-" You cut him off by pressing your lips to his.
"I'd love to Winchester." You said. He smiled and leaned down to kiss you again.
~Next day.~
Dean had told you he was taking you to a nice diner in town so you dressed semi formal. You actually put on a dress. When you walked into the room where he was waiting for you his mouth dropped open.
"Don't look so surprised Winchester, I know how to dress up." You tell him.
"You look beautiful." Dean said while walking over to you and holding out his arm for you.
"Are you saying I don't look good any other day?" You tease him, you tried to make things lighthearted because you could tell he was nervous.
"No, that's not what I meant." He says, you smile at him and he sees that it was a joke. He leads you out to where baby was parked and even held the door for you. He was really trying. Once you got to the diner you thought it was so cute, it was a replica of a 1950's diner. You ordered and soon enough your dinner was served.
"So, Winchester, when did you start liking me?" You ask him. He had calmed down quite a bit.
"Since you killed that demon when we met." He said.
"Yes, you were my knight in shinning armor who saved me." You said, with a smile.
"You would've got free, I just helped a little. You saved my ass more times then I can count." He told you before stuffing his face with his burger.
"So I guess your the damsel in distress." You tease him.
"No way, I'm a strong manly man." He says while puffing his chest out a little.
"Whatever helps you sleep at night." You say. The two of you continue to flirt and eat to your hearts content. He then drove the two of you home, to the bunker.
"Do I get a goodnight kiss?" Dean asks you once you reach your room.
"Do you deserve one?" You ask him. He simply nods and pulls you in for a kiss.
"Good night, Y/N." He says.
"Good night, Dean Winchester."
Sam:
You had been with the Winchesters for protection after the vamp incident. You and Sam had been having a little flirting war and Dean was sick of it so he made Sam ask you out on a date. You had liked Sam for a long time and he had to work up the courage to ask you out.
"Y/N, I was wondering if you would like to go to the carnival with me, as on a date." Sam asked one day when you were training with him. You looked shocked and just kinda stood still for a few moments.
