Awkward Questions to Ask People – 30 Questions You Should Avoid Asking

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There are plenty of awkward questions to ask people that may seem innocent and harmless in the beginning. But, in actuality, it bears deep-seated negative emotions – or it was simply because the other person was rude or awkward.

We’ve all this experience: we rejoin our family for Thanksgiving, head over to an after-party, or simply go to work for a normal day. Then, during ordinary conversations, someone asks us a question that throws us off guard. If we’re not prepared, we can get heated up and get into a fight. However, we can always take the intellectual approach and be prepared to dodge whatever is coming.

Some people just don’t know how they sound when they ask such questions. At times, we do the same thing. That said, let’s go over thirty of the most common awkward questions that might seem rude if you’re not cautious.

three women talking to each other - Awkward questions to ask people

Rude and Awkward Questions You Should Avoid Asking

According to a study in the ACM Digital Library, emotional bonding and common ground is an important component that helps us connect with others. Without this, chances are we won’t be able to empathize with the people around us. Thus, leading us to ask questions that are rather out of line.

In a different light, maybe these questions may seem harmless. Still, without the proper context, this could be easily construed as something insensitive or offensive. That said, it’s best to throw these queries with caution, especially towards people who don’t know you.

Let’s go over the different awkward questions to ask people sparingly and cautiously – about your personal life, work, and social events.

Awkward Questions about your Personal Life

Man making awkward face - Awkward questions to ask people

Anyone can throw these questions your way. However, the most common group of people who would ask these is your family. Some of us would expect that our family members would be more considerate and cautious about such sensitive topics, but this is not always the case. 

In cases such as these, one key thing to remember is to not respond with rudeness. In an article from The Spruce, they discuss that a similarly rude response may seem satisfactory but rarely achieves anything. Rather, it reduces you down to the level of the person who asked the unsavory query.

When this happens, the best way to approach this is to excuse yourself candidly as though you have something to attend to. If they start to be pushy, it always bears noting to give a warning shot. This means that you have informed your family that you’re not comfortable discussing these matters with them. You can also casually divert the topic to the food, recent events, or good news about your life.

Given that this is our family, we should avoid getting into a rift with them, since this can cause a more emotional toll on you than intended. If more uncomfortable questions are thrown your way after you’ve said your piece, then it is best that you just keep your distance for a little while.

  1. “How old are you?”
  2. “You’re still single?” Or “Why are you still single?”
  3.  “When do you plan on getting married?”
  4. “Are you pregnant?”
  5. “When are you gonna have a baby?”
  6.  “Did you lose weight?” or “Did you gain weight?”
  7. “When are you getting a real job, or a promotion?”
  8. “Does your job pay a lot of money?”
  9. “Is that how you dress now?”
  10. “What is your opinion on (a controversial topic)?”

Awkward Questions about Work 

two men sitting together awkwardly - awkward questions to ask people

When it comes to the workplace, you must be able to draw the line between what’s professional and what’s personal. This emotional boundary allows you to protect yourself from stress, fatigue, and gossip.

However, these questions hold the façade of curiosity. Behind these questions, we can never really tell if we’re being baited for gossip or some office drama. This is especially the case if you’re new to the job. When this happens, try to take a neutral stance and prefer not to say anything. Remember, if you have any problem with your boss or your co-workers, it’s more ethical to discuss this with the HR department first.

In the case that someone expresses their distrust or underestimation of your abilities, don’t be easily flustered. Keep your professionalism in the office, and be confident in your abilities. If they try to give you an unsolicited opinion, tell them “It’s okay, I don’t need it.”, or simply ignore it. When someone tries to stir things in the pot, just avoid anything controversial altogether. 

  1. “How did you land this job?”, “Did you get help from someone?”
  2. “What do think about (employer/coworker)?”
  3. “You think you can get the job done?”
  4. “What are you working on?”
  5. “What is your religion?”
  6. “How’s your love life?”
  7. “What are your political leanings?”
  8. “Why do you look tired/sad/angry?”
  9. “Do you need my advice?” or “Wanna know what I think?”
  10. “Will you be working here for long?”

Awkward Questions at Social Events

While your friend will more likely discuss sensitive matters with you in private, social events are sometimes where mutual or strangers get the chance to probe you for information. It doesn’t help that some people are already intoxicated.

If you’re on your own or don’t have anyone you trust to steer you away from bad company, be more cautious of your surroundings. Moreover, you have to be careful of the information you share, even if the questions seem innocent and harmless. Once these people poke into your personal life and are trying to provoke you, remember that you can always walk away. 

Steer Clear from the Malice

Take note that no one who has not earned the right to know intimate things about you deserves the answer to this. It is best to simply dismiss this kind of question, divert to a different topic, or call out the person for not minding their own business.

The rule of thumb stands that if we can’t change anything about this physical attribute, we should refrain from commenting about it. If someone feels entitled to mention such things to others, it’s best to avoid people like this altogether.

Furthermore, if people start fishing personal information that you are not comfortable with disclosing, you should keep your distance. That said, you can avoid the conversation altogether or divert the topic. This situation calls for the need for caution, considering that these are people you may not personally know.

However, there are a few ways you can counter these questions, especially if you’re feeling cornered and trapped. You can respond with, “Wow, you sure are nosy?” or “This is none of your business”. Another great approach is to outright respond with a “No.” and a straight face. If that doesn’t tick them off, spare yourself the torture and just leave the party. There are more social events more worthwhile for your evenings. 

  1. “Where are you from?” or “What are you?”
  2. “Where do you live?”
  3. “What do you do?”
  4. “Are you gay?”
  5.  “Are you gonna eat all that?” or “Do you eat or drink that much?”
  6.  “Do you still live with your parents?”
  7. “How much do you make from your business?”
  8. “You can afford that?”
  9. “Are you self-conscious about (a particular physical defect)?”
  10.  “How did you get invited? Or “Who invited you?”

Hear from People Like You

Rude and awkward questions are a universal phenomenon. All of us had experienced and said awkward questions to ask people to some degree. Where we differ is in our orientation, culture, and beliefs. That may sound utterly harmless to us, may sound derogatory and malicious to another. It is for this reason that we have to enhance our understanding by expanding our network.

That said, we invite you to join our Facebook group, where you can engage with different yet like-minded people. Discuss different awkward questions to ask people, and ask opinions from people of various backgrounds.

The art of mastery Facebook group

And if you want to learn how to improve your communication skills in all situations, check out my best-selling book, “Communication Skills Training: How to Talk to Anyone, Connect Effortlessly, Develop Charisma, and Become a People Person.”

Communication Skills Training book by James W. Williams

Closing Summary

 Now that we’ve discussed awkward questions to ask people, consider putting yourself in the position of whoever is probing you. Rethink on the possible reasons as to why they would need the information and whether this information can be used against you. You must pause before responding.

What tends to happen is that when anyone asks you something that is out of line, impolite, or even rude, you might freeze or start to babble out. Alternatively, you may start to feel irritated, insulted, or embarrassed. Both of these scenarios can reasonably impair our ability to react accordingly. That said, we hope that the advice we’ve given you proves helpful to you, and may also guide you to be more cautious when asking questions yourself. 

We’d love to hear how you’ve handled situations like this in the past. Feel free to sound off in the comments about any answers and quips you’ve responded to these tough questions.

Do you anyone who was just as unsure when it happened to them? You can also send this article to them so we can battle against such mindless and rude queries. 

We hope to hear from you!

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