From my mother, in front of a bunch of random people and my brother, "I know you're doing with that security guard, you sl*t!"
From my friend, "I don't want to hear about it."
From the brother of a guy I dated after I told him, "Well, did you learn from it?" everytime I tried to explain it to him, he'd ask that and no matter what I said, he'd say, "Then you don't need to talk about it anymore."
I started telling someone I used to be friends with about it, saying, "Something happened to me and I really need to talk about it." She completely ignored me and started talking to the people we were sitting with about anime.
From my mother, about molestation, "It's not molestation if someone's not disabled and they're over 10. They can fight, they just don't want to."
There's more I can't remember right now, but my mother is the queen of insensitive comments for sure.