Supernatural Boyfriend Scenarios

When he confesses to you (His POV)

A/N: I tried for this chapter. So I hoped you enjoyed the chapter.

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Dean:

Currently I was sitting in Baby waiting for Sam to bring the food along with the pie. While I wait, I noticed (Y/N)'s car pull up beside mine. Watching her get out that's when I think I should confess to her. Smoothly I get out of the car and stop her before she could enter the shop. (Y/N) looked at me oddly before sighing.

"Hello Dean. Do you need something?" She asked sweetly.

Why does she make me feel this way? How is she so cute? Now or never.

"Hey I was thinking we could go out sometime?" I asked.

Once I finished asking her, her face looked at me very confused.

"Dean are you asking me out? Or confessing to me? Cause I am confused, Dean."

Smirking at her as she asked if I was confessing to her. Before I could something, she spoke up.

"Dean I will admit I find you attractive. But I am not sure what you are saying. Cause I do really like you." She said causing my smirk to turn into a slight smile.

"Your not so bad yourself, (Y/N). I like you too. Now about us going out sometime?" I said causing (Y/N) to smile.

She agreed and kissed my cheek before heading to the store. This left me to smirk and get back into my car just in time for Sammy to get out of the store. Can't wait to see (Y/N) again.

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Sam:
(Y/N) was in the same spot she always sat in the library making me smile. I walk over to her and sat down. When she finally looked at me, her face lit up like a Christmas tree.

"Hey Sam."

"Hey (Y/N)." I said causing her to giggle.

"What's up?" She asked so sweetly.

"Looking at you." I said as my smile grew.

(Y/N) blushed causing my smile to grow even more. It's now or never.

"(Y/N), I like you and I was wondering if you would like to go out sometime?"

When I asked this, (Y/N)'s face went redder than before.

"I would love to." She said and kissed my cheek before hiding her self in the book she was reading before I got here.

She is so adorable. After a couple of minutes I leave to find Dean to tell him I asked (Y/N) out.

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Castiel:
I was sitting in (Y/N)'s car waiting for her to get out of the building she was in since she was on hunt. Once (Y/N) came out, she looked at me oddly making get out of the car.

"Cas, did Dean and Sam send you to bring me back? Cause I thought I had two more days left." She said with a laugh.

"No." I said confused at her laugh.

"I was kidding." (Y/N) said making me nod.

I looked into her (E/C) eyes as I decide to tell her.

"(Y/N) I need to tell you something that I do not understand myself. Every time I am around you, I feel different when I around you. Dean has told me that it means I like you. Will you go out on date with me?" I ask her.

(Y/N) looks at me in shock before slowly it turned into a smile.

"I like you too Cas and I would love to go out with you." She said before kissing my cheek.

Smiling softly, I pull her into a hug happy that she said yes to going out on a date with me.

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Crowley:
I sat in the throne room as one of the demons brought (Y/N) to. Once she was in the room the demon left with an eye roll. (Y/N) looked at me confused before I walked over to her.

"(Y/N), darling. I need to tell you something." I say making her eyebrow arch.

"What do you need to tell me?" Hearing the suspiciousness in her voice made me smirk.

"I like you. Will you be my girlfriend?" I ask her making her (E/C) orbs open wide.

She looked at the ground a second before taking a deep breath and looked into my eyes once more.

"I would love to be your girlfriend, Crowley." (Y/N) said before she hugged me.

Hugging her back, I was happy she agreed to be mine.

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Gabriel:
Watching (Y/N) was harder than it looked at times because I wanted to so tell her but still wasn't sure if I should or not. Currently (Y/N) was now standing in front of me making me smirk as I stare into her (E/C) orbs.

"Why were you watching me from a far? It creeped me out Gabriel." She said making me laugh.

"I wanted to tell you I like you but wasn't sure how." I said as I stopped laughing.

A smirk glue to my face making (Y/N) shake her head before kissing my cheek.

"I like you too." (Y/N) said taking my hand in hers.

"Want to go out with me?" Asking her now with a smile.

(Y/N) nodded and hugged me before dragging me off to help her with this hunt. She's perfect and I can't wait to take her out on our first date. What a perfect day.

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A/N: Happy Holidays. Hope you had enjoyed this chapter. I will be taking a break on December 27th after writing each of my books Holiday Specials. So yeah. Wait before I forget. I created a new book schedule and so here it is . Anyways hope you all have a wonderful holiday and happy new year. Please stay safe during this pandemic. :)