I haven't done a preference in so long so here's one now!
Imagine the boys asking advice on how to ask you out.
(Third person point of view)
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Dean:
"Hey, Sam?" Dean asked his younger brother in the bunker library. Sam looked up to meet Deans worried eyes. "How do I ask (y/n) out?" He asked. Sam laughed for a moment, but Dean looked as serious as ever, "Wait, you're not kidding" Sam laughed harder. "How should I know?" Sam asked because Dean was usually the one who was smooth with the ladies. "You're her best friend, and you're both geniuses, I figured you'd be able to help me out." Dean said, making Sam sigh. "Maybe say something really impressive, or intelligent?" Sam suggested to his older brother. Dean nodded, as if he were taking down notes in his mind.
"(Y/n)?" You heard someone knocking at your door.
You opened it to find Dean. He looked nervous, and kept looking at Sam for encouragement. "Are you made up of copper and tellurium?" He said, his voice shaking lightly. "Because you sure are Cu-Te." Dean finished, looking at the ground.
You began laughing. "You're so cute when you say things like that" You told him, who suddenly had a happier expression on his face. "Impressive, right?" Dean asked, which caused Sam to slap his hand to his head in the distance.
You laughed again, "Oh come here already" you said, pulling Dean into a soft kiss by the collar of his shirt, and Sam silently smirked from across the hallway.
Sam:
"Hey, Cas?" Sam asked him angelic friend. Castiel looked up at him, "Yes?" He asked. Sam took a deep breath, "You know (y/n) very well, and you're best friends with her, so I was wondering if you'd be able to help me out?" Sam told him, hinting that he wanted to go out with you, but Cas burrowed his eyebrows together, "I'm not sure what you mean by that." Castiel was still new to human emotions, "You know, help me ask her out." Sam mumbled. It took Cas a second, "Ah, I see what you mean!"
"She's very humble, so maybe something simple and endearing?" Castiel suggested. Sam nodded, "Okay, that doesn't sound too hard, will you be there too?" Sam asked, but Cas just tilted his head, not understanding why, "for moral support." Sam explained to the angel, who nodded, and zapped them to your house.
"You've got this, Sam" Cas said, right before he knocked on your front door.
You opened it, shocked to see Sam there, "Hey, what's up?" You asked Sam, who looked extremely nervous for a reason you didn't know. "I wanted to ask you something." As soon as he said that, your heart started skipping beats. You've always loved Sam, and Castiel knew it, so you could see him smirking.
You nodded, encouraging Sam to keep speaking. "I've loved you ever since I first met you, and I was wondering if you'd like to go out with me?" Sam asked.
You nodded, with wide eyes. "I love you too!" You shouted for all to hear. He knelt down and kissed you softly on the lips.
As you pulled away, you first went from Sam, to Cas. "Well, goodbye lovebirds." He said, and right before he zapped out, you saw him wink at you.
Castiel:
"Hello, Dean... Sam" Cas said, entering the bunker library where you, Sam, and Dean were seated. "Hello, (y/n)" He said, refusing to make eye contact with you. Hmm, that's weird, you thought.
"Dean, would it be okay if I spoke to you... alone?" Castiel asked.
You looked over at Sam, and then you two slowly got up and walked out of the room.
"What's the word, Cas?" Dean asked as soon as you and Sam were gone, "Its a shortened version of my name." Castiel said confidently. "Yes... it is, anyways, what's going on?" Dean asked. "You know how you're really close with (y/n)? Practically best friends?" Dean nodded, "I was wondering if you know how I should tell her I love her." Cas said, staring at the ground.
Dean laughed for a moment, but then realized that he was being serious, "Does wings here have a little crush?" Dean teased, but Castiel only grinned, "She truly is incredibly, and-" Dean cut his friend off, "I don't need the detail, but she likes it when people are straight forward, so don't hesitate to tell her." Dean told Castiel, who nodded, and then started walking to the hallway.
Cas pulled you aside, and Dean ran to watch, but be hidden from the two of you. "What's going on?" Sam asked Dean, and Dean just shushed him and told him to watch. "Is Cas finally asking (y/n) out?" Sam asked and Dean nodded, "Thank god, all she ever talks about is him." Sam said chuckling.
"(Y/n), I have something to tell you." Castiel started, wiping his sweaty palms on the inside of his trench coat. "I'm in love with you".
You took a step back for a moment, "You are?" You asked, and he nodded, meeting his glowing blue eyes to your beautiful (y/e/c) eyes. "I love you too." You said, embracing him into a tight hug.
