Supernatural Boyfriend Scenarios

They realized they made a mistake (His POV)

Dean:
I missed (Y/N). I miss her smile, her voice, her eyes and everything else about her. How could I be such an asshole? She was the best damn thing to ever happen to me and I fucked it up. I need to win her back; But first I need to find her. Let's just hope she will give me another chance.
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Sam:
I was sitting in the library when I saw someone with (Y/N)'s hair. At first I thought it was her but it turned out it wasn't. I missed her and hated how I hurt her. She was the greatest thing to have ever happened to me and I screwed it up. Maybe I can find her and ask her for a second chance. Maybe she will give me one.
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Crowley:
Ever since that demon helped my beloved (Y/N) to leave, I've been making that demon very uncomfortable. I regretted on what I did to (Y/N) and I miss her deeply. Truth is after she left I broke things off with the other woman I was seeing because I realized how much (Y/N) meant to me. I need to find her but I need that demon that helped her out to talk because I need her back. Hopefully she will give me a second chance.
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Castiel:
After I broke up with (Y/N), I regretted it. I missed her and after I found out that she ended up in the hospital, I blamed myself. How could I be so stupid? She was the best thing to happen to me. She was like an angel and I had to ruin it. I need to ask for her forgiveness but I have to figure out how first. I'll ask Dean and Sam to help me. Maybe they can help me get (Y/N) to give me a second chance.
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Gabriel:
Millia had told me that (Y/N) has refused to do anything she liked doing before. That broke my heart as I couldn't believe how much I have hurt her. Yeah I did regret dumping her but I also regretted not having her by my side every day. I need her back into my life and I will do anything to win her back. Let's just hope she will forgive me.
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Lucifer:
Ever since (Y/N) caught me cheating on her and left, my heart instantly broke. I missed her every day. I realized that after I might her. I miss her very much and want her back. Except I need to find her first. Hopefully once I find her, she will give me one last chance to prove to her on how much I love her.
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Jack:
Ever since I broke up with (Y/N) over a stupid fight between us, I instantly regretted it. No one has seen her since that day and I was worried. She barely leaves her room. She also hasn't eaten or drank anything for weeks. I need to get her back. I miss her. Hopefully once I can she will give me a second chance for when I ask her.
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Balthazar:
It's been awhile since I have seen (Y/N) and I miss her. Everyday I regret what I did to her. I shouldn't have cheated and I shouldn't have let her go. I'm such an idiot. She was the best thing to ever happen to me and look at me now. I'm getting drunk and causing problems for the Winchester's. I need to find (Y/N) and win her back. Then maybe she will realize that what I did was one simple mistake and she is all I need.