Dean- you are afraid of flying but for your 3rd year of dating, he planned an anniversary vacation for a couple of weeks in Hawaii. You were siked but the plane was the downside. He too, is afraid of flying so you were both jumpy whenever something didn't feel right. You were both whispering christo the plane ride, but since he was scared too it was kind of comforting in a way.
Sam- it was your 3rd year of dating so when you said you wanted to see Paris he took you. He told you to close your eyes and then he led you into the Eiffel Tower and into an elevator all the way to the top. What he forgot was that you scared of heights. When you got to the top he told you to open your eyes so you did. "Oh my god Sammy get me down, oh my god oh my god oh my god." You started shaking and he held you really tight and took you back down. When you got to the bottom he comforted you and you both just went out for dinner.
Castiel- it was your 3rd year of dating and you always wanted to see an aquarium so he took you. You wet having so much fun, until you decided to walk in a different direction. You saw this huge creature swimming and heading towards you. "Wait a minute. CAS!!!!!!!!" It was a shark your worst fear. You were FREAKING OUT! You let out the loudest scream imaginable, followed by crying and even more screaming. The shark hit the glass and you were face to face with the worst possible thing imaginable times ten. You knew the glass separated you but to you the glass wasn't there. "CAS IM GONNA DIE!!!!!!" You literally fainted but he healed you. "It's ok heart, I'm here." He looked at the shark and laughed. You were still crying really hard but he couldn't understand why you so scared of sharks. "Hey! It's not funny cas!" You said through tears. You playfully hit his chest to show you were mad. He kissed you on the cheek and picked you up bridle style and carried you that way the rest of the day. You had nightmares about that day sometimes but he always comforts you.(my worst fear I had a nightmare and this story is what I got out of it.)
Bobby- he took you on an anniversary trip. But he took you to a fancy restaurant in a fancy hotel. This meant taking an elevator. And did I mention, you have claustrophobia? Oh, well you do! You were crouched down swaying back and forth with your hands on your knees. He gave you a tight squeeze on the shoulders. "You are my sunshine my only sunshine you make me happy when skies are grey you are my sunshine my only sunshine please don't take my sunshine away" pretty soon you were both singing along. Bobby's voice was always comforting and you both got to have your anniversary dinner.
Crowley- it was your anniversary and he took you to a sketchy looking building. But once you got there, there was a spider. you his behind him and he killed it then laughed. "really love? I'm the king of hell, and you're afraid of a spider?" "Shut up Crowley!"
Garth- you were afraid of thunder so he played the song thunder struck by acdc and made you laugh. you loved how he could always make you laugh, even when you're scared.
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FanfictionIncludes castiel dean Sam Garth bobby Crowly feel free to request