Dean grew up hating the supernatural since his mother’s death when he was young. His father’s hatred for them and growing up to be a hunter only fueled it and thought that all monsters were heartless and cruel. However, he noticed that his younger brother, Sam, thought differently than him and sometimes gave monsters a chance.   Dean met you during a hunt and has grown attached to you over the years. He never knew your true identity until you had to use a spell to save his life. When you did, his eyes widened as he realized that you were a witch. He was conflicted with doing his job and killing you, but he knew he could not do it. He thought about all the times Sam was sympathetic with monsters and he wanted to give you a chance too.   He looked at you for a moment before letting out a sigh. “You’re a witch. That’s… cool. What’s that like?” He asked as he mentally facepalmed himself for what he just said. He had a feeling this would make things awkward between you two, but he genuinely did not want to ruin his friendship with you.