Question to Ask the Workplace Doctors about belittling comments: I never know what to say back in the moment so I just laugh with her (at myself! yuck) or just respond promptly to her question.
My boss and I used to be very good friends and are still friendly at work but not outside of work (just due to life circumstances). My boss consistently makes observations and comments. She says them in a joking way but they are annoying to me because they make me feel self-conscious and picked at. I said something to her about it a couple of years ago (in a nice pleading way) and she said that I was too sensitive and that that is how she acts when she likes people.