Oh yeah, this one's quite recent.
So my uncle had come over for dinner one night, and I was getting the ice cream out for my family. I had asked my mom where this one type of ice cream that we had was, because I didn't see it in the freezer and she replied saying that she had eaten it. I joking said to her, " And you're always complaining about your weight! " Then my uncle came in and said " Well what about your weight?" He meant it in a funny way, but that really, really hurt. I've had eating disorders in the past, so you can image the impact that that had on me.
I'm still hurt by that, even if he didn't mean it.