Two that still make me wince:
At work, one male colleague told another that I should be “over” my termination for medical reasons by now, shouldn’t risk trying for another baby, and should “get a dog instead.”
I didn’t even overhear this - the second colleague thoughtfully relayed it to me, thinking he was being helpful, finishing with: “Have you thought about getting a dog?”
For extra irony, I’m allergic to dogs.
The other was at school. A popular boy never missed a chance to make comments within earshot - “why does she bother with lipstick, you can’t polish a turd,” “stuck-up swot who’ll be a virgin forever,” etc.
In sixth form, I crossed paths with him in a nightclub. When I went to the bar, he approached my boyfriend and asked him what he was doing with “a sad minger like her.” I never retaliated, despite him not exactly being blessed in the looks department - think Humpty Dumpty.
He’s now a police sergeant, and I had to laugh when he recently posted on our local Facebook page about cracking down on teenage bullying in the village.