We know he was doing it by the time they were trying to find Lilith in season 3, because of episode 7.15, "Repo Man", where it flashes back to during that time when they were trying to find a way to save Dean's soul from going to Hell. At that point, they actually got the permission of the human that was being possessed to torture his body so that they could get information out of the demon that was possessing him... then they dropped him off at a hospital afterwards.
Over time the boys have both become more hardened to that sort of thing, don't seem to see it the way they used to. :/ It definitely bothers me, too. :(
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We know he was doing it by the time they were trying to find Lilith in season 3, because of episode 7.15, "Repo Man", where it flashes back to during that time when they were trying to find a way to save Dean's soul from going to Hell. At that point, they actually got the permission of the human that was being possessed to torture his body so that they could get information out of the demon that was possessing him... then they dropped him off at a hospital afterwards.
Over time the boys have both become more hardened to that sort of thing, don't seem to see it the way they used to. :/ It definitely bothers me, too. :(