He ask you out:
Dean: About a week after you date, is when he popped the question. The both of you had taken a walk in the park on a beautiful day. When you found a bench, he sat you down the sat right next to you. He took your small hands in his as he look into your eyes. I swear to good those eyes are going to be the death of me. "Y/n I know we've only be friends for about a month now but I'm really starting to like you. So.. I uh was wondering if maybe, i don't know, uh you might want to be my girlfriend." He stated awkwardly. You laughed at his nervousness. "I'd love nothing more than to be your girlfriend Dean" you smiled wildly at him, witch he returned. He leaned in and planted a light meaningful kiss upon your lips. He pulled away as you blushed. Today was the best day of your life.
Sam: Sam was the sweetest thing ever!! He definitely knows how to treat a lady. He asked you out in a the most romantic way ever. He had invited you to the bunker, so of course, you went. When you had arrived, he was waiting for you outside the door. You have been dhere, prior to being friends with dean. We led you into the living room type thing. "Wow it smells really good in here" and just as you said that you saw the most beautiful scenery you've ever seen. There were candles all over the room. And when you looked down, there were Ross pedals laid out on the floor that spelled something out. It took a second for you to realize what it said. When you finally saw it, it read out "will you go out with me?" You smiled and looked up at Sam. "Yes, I will go out with you" he grinned at you, pulling you in to a kiss. "Oh god. It's like another chick flick" dean interrupted. Yall didn't pull away, you just flipped him off, pulling Sam in to make the kiss deeper. Dean groaned as you and Sam just laughed into the kiss.
Cas: Cas was very awkward about it. You were at you your day job. You were a doctor. You were filling out some papers, when all the sudden, Cas zapped in front of you. "Oh my god Cas! You gave me a heart attack." You yelled. Good thing you were in your office were no one could hear you. "Well we do not need your heart stoping Y/n" Cas said seriously. You just laughed art his confusedness. "So what do you need Cas?" You asked. Cas looked at you "well I really like you, and Dean said I should say this: "Y/n I really like you and I want you to be my girlfriend." You smiled up at him "Cas I would love to be your girlfriend."
