Supernatural Imagines

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Could you do one where dean asks the reader to be his girlfriend and she hesitates to say yes and she explains that its not a good idea because she's insecure and anorexic and he cheers her up and promises itll get better? I love your writing and I could use some cheering up. Super fluffly please?(:

Anonymous

Hi. I’m so, so sorry this wasn’t done sooner. I really hope it cheers you up. And if you need anything, message me.

TRIGGER WARNINGS: hints at anorexia, reader talks about their insecurities.

~~~~~

You were curled up on your bed in the bunker, watching reruns of your favourite TV show. You had the blankets tucked up around you and the remote clutched in your hand. Someone knocked on the door and you pressed the mute button. “Who is it?”

“It’s me,” Dean’s voice answered. “Can I come in?”

“Sure,” you replied. He opened the door and stepped into your room, pulling the door closed behind him.

“Nice,” he said, nodding in approval at the band posters you had pinned up on the walls.

“Thanks. What’s up?”

Dean coughed nervously, coming over to sit at the end of your bed, being careful to avoid your feet. “I don’t really know how to say this,” he told you, reaching up to scratch the back of his neck. His eyes darted around the room and you smiled up at him encouragingly, patiently waiting for him to say what was on his mind. “Y/N, we’ve known each other for a while now. And…I really like you. And I was wondering if you’d like to go on a date with me?” he asked carefully, each word coming out slowly.

You froze, staring at Dean like a deer in the headlights. “Oh, um, Dean…I’m flattered. Really, I am. It’s just…”

“Oh,” he said in disappointment, looking down and swallowing. “It’s okay, I understand. I just…never mind.” He started to get up, but you reached out to grab his arm.

“I don’t think you do understand,” you told him. “Dean, I really like you. I’d love to go out with you. But…”

“What is it?” he asked, concern spreading across his features. He say back down on the bed, his eyes focused intently upon you.

“Dean, I have a lot of insecurities. I mean,” you lowered your voice, “I can barely eat without hating myself. How am I supposed to be in a serious relationship with all those problems in my life? So many girls come up to you in bars and pretty much everywhere else, all looking to get your number. How am I supposed to compete with that?” You looked down, trying to hide the tears that had sprung to your eyes. “How am I supposed to handle that kind of pressure?”

“Y/N, look at me.” Dean’s hand reached out, gently cupping your chin and turning your face towards him. “None of those girls is any match for you. Trust me. You blow them all out of the water with your awesomeness.” You smiled at him weakly, sniffing back the tears. “And the other stuff you mentioned? We can get through that. Together. I promise I will never leave you on your own in this. Things are gonna get better.”

“Do you really think so?” you whispered, your voice cracking. Dean’s hands came to rest on your cheeks, his thumbs wiping away the tears that had leaked from your eyes.

“I know so,” he confirmed. You wiped your sleeve across your nose, glancing him at him, at the determined look in his eyes.

“Then…maybe I’ll take you up on that date,” you told him, a soft smile spreading across your face. Dean grinned back at you, his eyes lighting up in joy.

“Awesome.”

~~~~~

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