We all have a natural curiosity about the people around us. Whether it’s a co-worker, a neighbor, or even a stranger, there’s always something we want to know about them. However, some questions are more uncomfortable than others.
This list contains some of the most uncomfortable questions you can ask someone. But before you ask any of these questions, be sure you’re prepared for the answer – whatever it may be.
16 uncomfortable questions to ask your friends:
- Who was your first kiss?
- What was your first kiss like?
- Have you ever had a dream about me?
- What’s your biggest fear?
- Do you have any exes that you’re still in touch with?
- What do you like least about me?
- What’s your opinion on gun control?
- Who is one person you envy and why?
- Have you ever cheated on a partner?
- What’s the wildest thing you’ve ever done?
- Would you ever consider an open relationship?
- What do you think about marriage and/or children?
- Do you have any dark secrets that I don’t know about?
- Is there anything about me that you don’t like but haven’t told me yet?
- Who is one friend that you feel like you can’t be yourself with and why?
- Would you ever date someone outside of your race/ethnicity/religion?
12 uncomfortable questions women ask men:
- What do you think about feminism?
- What do you think about gender equality?
- What do you think is the biggest challenge for women today?
- What do you think about abortion?
- What do you think about sexual assault?
- What do you think about the wage gap?
- What do you think about the way women are portrayed in the media?
- Do you think there are double standards in society when it comes to how men and women are treated?
- Do you think that men and women are equal?
- Do you think that men have an advantage over women in society?
- What do you think about beauty standards?
- What do you think about women’s rights?
12 uncomfortable questions men ask women:
- How do you feel about abortion?
- Do you want to get married someday? Why or why not?
- Do you want children? How many?
- How do you feel about religion and/or spirituality?
- What do you think about celibacy/abstinence?
- How do you feel about birth control?
- What is your relationship history?
- How do you feel about surrogacy?
- What is your opinion about prostitution?
- What is your weight?
- Do you think there’s a difference between the way men and women think?
- What do you think about men who cheat on their wives or girlfriends?
11 uncomfortable questions to ask your colleagues:
- What do you think about the recent layoffs in the company?
- Do you think the company is doing well or is it having problems?
- What do you think is the biggest weakness of our team?
- Have you ever felt uncomfortable with the behavior of a colleague?
- What do you think about the way the company is run?
- What do you think about the company’s benefits package?
- Do you think the company is fair when it comes to promotions and raises?
- What do you think of the company’s policies against sexual harassment and discrimination?
- Do you feel like your workload is manageable or too heavy?
- Are you satisfied with your current job or are you looking for a new opportunity?
- Do you feel that your contribution is valued or disregarded by management?
14 uncomfortable questions to ask your partner:
- What do you think about monogamy?
- What do you think about open relationships?
- What do you think about polyamory?
- What is your definition of cheating?
- Have you ever cheated on a partner?
- Do you have any dealbreakers in a relationship?
- How do you feel about divorce?
- Are you ready to settle down?
- What are your thoughts on children?
- What do you think about swinging?
- Do you have any medical conditions that might affect our intimate relationship?
- Are you taking any medications that may affect our intimate relationship?
- Do you have any STDs or STIs?
- Have you ever been tested for STIs?
16 uncomfortable questions you should ask yourself:
- What am I afraid of?
- Why do I want what I want?
- What do I like least about myself?
- Who do I not want to forgive and why?
- What are my biggest insecurities?
- What am I most ashamed of?
- What do I most fear about the future?
- What is something I once believed in but no longer do?
- Who has hurt me in the past and why am I still holding on to that hurt?
- What am I holding on to from my past that is no longer serving me?
- Is there a grudge that I’m holding on to? If so, why?
- What things do I need to let go of to move forward?
- Why do I feel that I’m not worthy of love and happiness?
- When was the last time I paid attention to my mental and emotional health?
- What are my greatest failures?
- What do I need to change about myself?
Frequently Asked Questions
What does it mean when you get an uncomfortable feeling?
An uncomfortable feeling can mean many different things depending on the person. For some, it might be a sign that they are anxious or stressed about something. For others, it might be a warning that something is wrong.
If you’re feeling uncomfortable, it’s important to pay attention to what might be causing it and address the problem directly. Ignoring the feeling can sometimes lead to bigger problems down the road.
Why is it important to feel uncomfortable?
It’s important to feel uncomfortable because we learn and grow through the discomfort. When we’re faced with something that makes us uneasy, we are forced to confront our fears and figure out a way to overcome them. This can be a challenging but rewarding process that helps us become stronger and more resilient.
Discomfort can also teach us something about ourselves and allow us to discover new aspects of our personalities. By embracing discomfort, we can learn new things about ourselves and become better people overall.
These are just some of the most uncomfortable questions you can ask someone – but that doesn’t mean they can’t be interesting and insightful conversation starters. If you’re curious about the people around you, try one of these questions (but be prepared for anything).
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