AU in it's a Terrible life 5 years after that unfortunate black mold/carbon monoxide leak whatever and Dean Smith has a beautiful secretary (Lisa or sth) he occasionally fucks in his office because like Adler told him he's now basically living in his office and one morning Lisa's gone and Adler tells him his nephew is deans new secretary (he owes his sister big time) enter goth tattooed castiel looking like everything dean shouldn't want even if Charlie from IT (new Ian) finally broke him out of his closet and he barely does the job but he does it and one day the kid doesn't show up to work and deans worried okay and cas relapsed and is riding out cold turkey at home or something like that and just like slowly it builds until they actually get to a point with a good work relationship and cas is wearing almost business attire even if there's a leather harness on his white shirt instead of a tie and there's still tattoos and makeup and his hair is a mess but dean knows it's the best he's gonna get and he loves him and they go home together at a reasonable time awwh (also Cas is taller than him in his boots, always) (idk how old cas is here very late teens early 20s ish?)