What are the best rude and offensive questions to ask someone?

To a woman: “are you pregnant, or have you gained weight?”

Traditional (to a male): When did you stop beating your wife?

Unisex: Was that your husband / wife that I saw eating with you at the fancy restaurant last week?

“Are you pregnant” was the first thing that came to my mind @elbanditoroso. There was a time you could actually tell the pregnant women from the non-pregnant women. But I guess that was about 20 years ago.

“What are you?”

 
Wait, that’s not good for the phone. That’s better when you can peer into someone’s face in a presumptuously entitled way and speculate about their ancestry, ethnicity, race, age, gender, etc.

I wouldn’t take offense if someone asked me “What are you?” knowing they’re asking where I’m from, or where my ancestors were from.

So if you ^^ wouldn’t take offense, does that mean that no one else would, or no one else should?

I had a Japanese-American friend who used to get asked that a lot, just standing in line somewhere like a bank or supermarket or walking around a store: a very quizzical “What ARE you?” as if she were some alien species. It was she who made me aware of how some people get approached when they don’t appear to fit neatly into some classification.

If you had stayed in school what kind of job would you be doing right now?

What are you going to be when you grow up?

No. Doesn’t mean that at all @Jeruba. It’s just me. I wouldn’t be offended if I was in a predominately black country and was asked what my nationality is. Of course, it would also depend on how it was asked, and the tone of voice.
When I visit my family in the Pacific Northwest I am often asked where I’m from because, apparently, I have a bit of a Southern accent. It’s human nature to be curious about strangers.

“Where are you from?” doesn’t sound at all to me like “What ARE you?” but maybe it does to someone else. At any rate, a rudely inquisitive demand for an explanation of one’s appearance might well be received poorly by some.

However, none of that plays over the phone, which is what the OP asked about. Sorry, @lucillelucillelucille.

That it is a phone call makes things much harder.

Do you have a breath mint? It is bothering me right through the phone.

So, who are you screwing this week?

My ______ is missing. Did you take it?

Start talking a little louder. Can you hear me okay? Talk a little more louder. Can you hear me now? Keep that going.

“Is this going to take long? I have to pee.”

“I’m sorry, could you repeat that? I was thinking about something else.”

“I’m on 35-across. What’s a six-letter word for ‘dull’?”

I have UTI. Any suggestions?

My god but you’re ugly, did your mother feed you with a catapult?

Personalo questions asked to someone you don’t know. How much do you make, how old are you, how much do you weigh.

Has anyone said you look like Ted Cruz?
A cross between a permanently disappointed sitcom vampire and the high school yearbook photo of every serial killer of the modern era.

Could you lower your voice?
It sounds like you have marbles in your mouth, are you eating?
Did you just (insert body function here.)
Can I call you right back, have to let the dog our?
Can you hold, I have another call.

I wish I had context, I’d customize for you.

Would it bother you if I flush right now; should I wait?

Have you ever woke up and blood is all over you, but you don’t know here it came from?

Can you tell I’m not listening at all?

Do you have a little tail? I heard some people are born with one. Can you wag yours?

@PattyMelt haha the flush is really good!

“I really like the shirt you’re wearing, where did you buy it?”

It’s not rude, but it would probably creep someone out over the phone if they thought you were watching them.

Lol! I have actually done that a few times. You hear them squirm around like they are looking for who’s watching. One of those times it was a friend, and she insisted I tell her how I knew what she was wearing. I said I’m right here, look, I’m waving. I wasn’t even in the same town.

“I don’t know of anything worse after an all night binge than waking up next to someone and not being able to remember her name, how she got there, and why she’s dead. That’s when I say “I’m never doing this again!” Followed by “And this time I mean it!”~ AstroChuck.

So, @lucillelucillelucille, what did you say—and why did you want to be insulting?

@Jeruba – I thought she needed to be energized.
I found a bike horn in the shed so I didn’t have to say much. XD
I’ll see her this weekend and I am bringing the bike horn so if you never see me back on this site,she did away with me.
She is my sister. (for suspect identification)

Ohhh—insults for sisters. Why didn’t you say so?

It does put it in a different light.

“I’m an only child.” (Ok, so a direct rip off from The Smother’s Brothers, Mom liked you best.)

@Jeruba _I didn’t want to say anyone’s answers but if have any good ones,go for it!
@Dutchess_lll- Been there before XD

Oops “sway”.

Oops “you”.
I need a nap lol

You call that a nose, or is that a banana glued to your face? Is it true that you used to dance in a flea circus? Is it true that your girlfriend left you when she regained her eyesight? If they put your brain in a matchbox. does it sound like a bb rolling around in a railroad box car?