What's the most offensive or inappropriate question you have ever been asked?

At truck driving school, “How many times did you cheat on your wife?”. Guys were all standing around, ‘bragging’ about their number. At this time I was married about a year, said zero. Offensive question number 2 followed. “A year? When are you going to cheat, then?”. I said never, then got ridiculed. 30 years later, that number remains zero. Always will. I still drive for a living.

As a young woman with large breasts I was often asked “Are those real?” by men. The question was often accompanied by a hand reaching out to test.
I developed a pretty good right hook.

Same @canidmajor. “There is no way you can be so skinny and have boobs that big! They must be fake!”
Never got that crap from girls or women.

A Friend: “When is the baby due?”
Me: (just married): “She isn’t pregnant!”
An Ex-Friend: “Of course she is! You never would have married her otherwise!”

OMG!

@filmfann I’m not “wired” quite right, that took me a minute.

A female friend and co worker once tried to persuade me to go home with her after work, while her hubby was out of town. For a dip in her pool supposedly. I passed. Not offensive but inappropriate fore shore. Think she wanted s dip,but it had nothing to do with a swimming pool.

Oh yeah, she wanted “cooled” down, but I think her pool would have heated things up!

Me too. We didn’t need to be alone in her pool at two in the morning.

Why are you so skinny? I’m kind and don’t say what’s on my mind (Why are you so fat?).

@NoMore You may have mistook what I meant by her “pool” it may be wet but it’s not cool.

Lol no comment, mixed company in here. ; )

Two female medical scanners laughed at me said that they couldn’t find my testicals. I was in pain and didn’t need the embarrassment.

Asked by a bar maid: “Do you wear boxers or briefs?”

That’s weird @kritiper.

It’s the one every girl gets asked, when she’s in the wrong place with the wrong men :

“You don’t understand why we charged so much for an oil change ? Can you just call your boyfriend, and let me talk to him?? ”

…But actually, it’s the second most offensive thing I get asked. ; p

I was shorter than most of my classmates at school and a bit younger but it filled me with embarrassment when the bus conductor asked my age when I offered to pay full fare.

Probably this pair, from a Russian stranger (no, not that one, some fugitive Russian, in person, in 1987):

“How did you masturbate while traveling with your mother?”

followed shortly by:

“Why don’t you kill your parents?” (Note: I had given no indication that I had any animosity toward my parents. He just said he thought it was a good idea . . .)

@Zaku My mouth is hanging open…

@Dig_Dug I can imagine. And, oh yeah, he then went on to suggest that I should have children of my own as soon as possible, because “children prefer their parents to be young”. I wondered, but I think I didn’t ask (or I did but he didn’t answer), whether I should also expect my children to kill me as soon as I came of age.

@Zaku I just can’t ..I mean, where do people come up with this stuff?

I can’t possibly type it here.

@Dig_Dug I don’t know, but it seems like “Russia” may almost be an accurate answer. That is, while I’ve only had prolonged conversations with a half-dozen or so Russians over the years, I think 100% of them have brought in one flavor or another of severely bizarre, violent, and/or delusional views and ideas. I guess I should make that a question here.

This person otherwise seemed intelligent, educated, experienced, and somewhat sympathetic, positive, and interesting.

@Zaku That is a very scary combination.