somewhere around the beginning of SPN S14 after Michael is gone
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26 Dec 2018
They are semi-retired, no assassinations attempts, no angelic or demonic possessions in a while. But Dean is still gloomy and he’s also still not asking Cas out, and Sam’s just had it. He could try to talk some sense into Dean of course, but that’s never worked all that well. So instead, he does something drastic: He nominates Dean for the fabled Queer Eye makeover. Needless to say that the Fab 5 have their work cut out for them.