15 Examples Of Times It Could Actually Hurt To Ask

Popular sayings usually get that way for a reason, and I’m certain that the majority of people in this world have been told more than once that “it doesn’t hurt to ask.”

The idea, of course, is that if you want something, you’ll never know whether or not you could get it unless you simply ask the question.

Cool in theory, but as these 15 people point out, there are times when that’s not at all the case.

15. The real cops.

In college some friends and I got caught smoking weed in a park by a park ranger.

He was pretty cool and it seemed like we were going to get away with a warning until my one friend piped up and said

“You’re not going to call the real cops are you?”

Dude’s attitude towards us did a 180 real quick.

“You see this gun? You see this badge? I am the real cops.”

14. Someone will hate you.

“Hey teacher, are you going to collect the homework you assigned yesterday?”

13. Internal screaming.

Any question from a supposed authority or expert that reveals a complete lack of understanding of the matter in question.

E.g., a judge who once asked why the YouTube video under evidence could not be printed for him to review.

There’s nothing worse than the internal screaming when you realize that your work and company’s reputation is now completely hostage to someone who hasn’t the faintest idea how what you do works.

12. Don’t ask that.

So uhhhh… do you guys do random drug tests?

I just interviewed for a new job. And my only question for them was do they test for weed. Of course I didn’t ask but that was the only question I had. It was too painful to ask.

11. I am cringing. Hard.

As a server, “Where’s that other woman you always come in with?”

Retail too.

I’ve got a regular that would always come in to get his cigarettes. Marlboro red black shorts, and Marlboro special lite shorts. Every time I see him walk in the doors, I’ll get his cigarettes ready at the counter for him.

One day I hear that his wife died, and I didn’t see him for a week. Once I do see him, I get them out of the case and ready for him. Once he’s at the counter and sees them, he just sadly says “no lites this time”.

I felt terrible

10. I mean. It can’t be the first time.

As a teenager I worked in a grocery store, I saw a customer who’s back was to me struggling with all there items, so I asked “do you need a hand?”.

The man turned around and I could see he was missing a hand, there was just a stub there, that is why he was struggling. He was a good sport and said “Yes, it seems I do!”, lifting his arm missing the hand in the air.

9. No matter how frustrating it may be.

the name of someone you’ve known for awhile

I once had a friend in college that it took nearly 6 months to figure out his name even after going out for drinks after our evening class every week.

I think both of us didn’t want to admit we didn’t know each other’s name so we just went with “buddy” for months until we recognized another student at the bar and we introduced ourselves and realized we were finally going to learn each other’s name

8. Just don’t.

“When are you going to have children?” or any variation.

Be ready to be told they’ve lost a baby, infertility, sexless marriage, etc.

Just don’t.

7. Yes, exactly that.

Between one of my friends and a random person at the blood bank (I was donating and we were going to go get lunch afterwards).

Stranger: Are you going to donate too?

Him: I would if I could, but medically I can’t.

Stranger: Why? You got HIV or something?


He did in fact live with HIV.

6. Not a lie.

One day back when I was at school, I didn’t have my phone on silent, and it went off during class.

The teacher thought he’d make an example out of me and ask who the text was from. I replied “My Mum. She’s in hospital with cancer.”

He shut right up and went back to the lesson.

(She was being treated for Stage 4 bowel cancer. She had a 25% prognosis, so naturally everyone was on edge.

That was almost 15 years ago, and fortunately she’s still with us, and got the all clear some time ago).

5. That one hurts.

What happened to your baby? I thought you were pregnant?

My husband teaches high school and told everyone we were expecting at the end-of-school picnic. I was 20 weeks pregnant. We got a fatal diagnosis at the anatomy scan the very next day and lost the baby two weeks later.

We did a lot of mourning over the summer. When he went back to school this fall, BAM. First question everyone had.

4. Awkward.

At military school, many years ago, an upperclassman friend was giving some shit to a plebe. As one does.

U/C: “And why are your glasses crooked. Put ’em on straight!”

Plebe: “Sir, I was in a car accident as a child, my right ear and right eye are 3/4 an inch lower than my left, that’s the best the surgeons could do. Sir.”

U/C: nothing, peers at each ear, sees the scars

U/C: “Uh. Carry on.”

3. Never again.

I worked with a guy on a day shift for a few years, last I saw him his wife was 8 months pregnant, he was pumped to have his first kid, I switched to a night shift same place, came back to days over a year later, saw him and asked how the little one was…his baby passed around 2 weeks old…

I had no idea…I had no way of knowing…I’ll never ask that question again it gutted me on the spot and I still feel bad even though it was a long time ago, good intentions, bad idea

2. Be prepared for the answer.

One of my friends has a sister that is battling cancer. I always want to ask how she’s doing, but I fear the worst.

Also, I would feel bad if I didn’t ask.

1. Just don’t do it.

My wife retained a bit of a belly after our second child. She met someone she knew at the store and they asked “Are you pregnant again?”

I felt horribly bad for my wife. I could tell that hurt her more than a little bit. Never ask a woman if she is pregnant.

I’ve never really considered this question, but sure. There are always times when keeping your mouth shut is the way to go.

Can you think of more examples? If they’re not on this list, hit us with them in the comments!~