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How to handle uncomfortable questions or conversations

Have you ever been in a situation whereby someone wanted to discuss something that you’re not comfortable with or they asked you an uncomfortable question about your personal life?

I’ve been in this situation so many times and was in this situation just this week.

I was actually quite stunned to find out the length at which people can pry into your personal life. I would think twice before asking someone a personal question or making someone uncomfortable, however, there are plenty of folks out there who seem to get a high off making another person feel uncomfortable.


So how does one handle uncomfortable questions or conversations?


  1. Take a deep breath, keep calm and be positive & open-minded

One thing that I’m always aware of is that my response will always be a result of how I perceive a matter based on the countless experiences I’ve had, both good and bad.

My reaction when someone asks me something that makes me uncomfortable might not be the right one.

Hence, as soon as someone asks me something that hits a pain point or makes me feel uneasy, I pause, take a deep breath, collect myself and open my mind.

I have to assume that perhaps this person does not have any ill intentions and I’m looking at this the wrong way until I can 100% come to the conclusion, that actually this person is an idiot.

Staying positive whilst pretending that this person is an alien who is just curious, I keep an open mind and try to answer the questions as best as I can.


2. Put yourself in their position – why are they asking this question?

As I try to answer their questions or continue the uncomfortable conversation, putting myself in their position also helps with keeping my open-mindedness alive.

I always try to find out their reason for asking this question or having this conversation. Maybe he/she isn’t really a prick, but just curious or they need help with their own situation.

Also, putting myself in their position helps me to assess whether I’m overreacting to the situation.


3. Their reason is not good enough – be polite and try to end the conversation

If I still don’t feel comfortable answering their questions or continuing the discussion despite having been told their reason for asking and putting myself in their position, I politely say I cannot continue this conversation.

Yes, it’s good to be open-minded but you also need to respect your feelings.

There is absolutely no reason for someone to make you feel uncomfortable. Most times, they are in a poor state of mind and are trying to spread their negative energy to you – you don’t need that. Maybe they believe strongly about something and feel the need to impose that on you – you don’t need that either.

Simply end the discussion by being honest and telling them that you are not comfortable continuing the discussion or answering their questions. If he/she is a decent person, they’ll respect your feelings and let it go.


4. Change the topic of conversation

If I’m not comfortable telling a person directly to back away or I don’t want to hurt their feelings, I try to change the topic or ask them a question back 😀 not one that is as disrespectful as the one that they have just asked me but perhaps something that they are interested in talking about.

I compliment them on something they are wearing or I talk about the dessert I’m looking forward to trying at the party. Everyone likes talking about dessert 🙂

You could also make the conversation less awkward by inviting someone else to join in and somehow change the topic.


5. Walk away

Yes, there are some people who are just plain rude or enjoy making others uncomfortable.

No matter how much you try to reason with these people, there won’t be an amicable outcome.

The best thing then is to walk away. I just politely excuse myself and there’s no need to feel bad. They are the ones who tried to make me uncomfortable and would get the point.


Dealing with people who ask you uncomfortable questions

So how do you deal with people who ask uncomfortable questions or enjoy having uncomfortable conversations with you?

Feel free to comment below!


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