i really hope i covered everything...
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Dean, Alec and Izzy regularly went on hunts together. Maryse knew, while she didn´t exactly agree, she let them as long as her children still did the missions she sent them on.
John didn´t know, he didn´t even know Dean met other hunters.
also inspired by this prompt: https://promptsforyourwhumpfic.tumblr.com/post/177371753435