IMO while he may have been trying to "joke", "tease" or otherwise cajole you in what he perceived as "good-natured" way, he was overtly establishing his view as the "correct" one. Which is why HR steps in and says that is a no-no.
Sometimes the folks who work at these type of jobs, with little to no human contact, lose that "friendly" tone, and that can make a comment hurtful. Whether it was intentional, or unintentional is not the point, it's that it had passed the point of being "cute" and "funny-ha-ha".
When he lost the playful tone is when it went stale.
EryLynn
