Sometimes we consider that our partner knows us well enough and we take it for granted that they are capable of answering many of our questions just as we expect or think. For this reason it is so important to know that sometimes it is better to ask to get to know that person with whom we share life better. In this article we share uncomfortable questions for your boyfriend or girlfriend.

25 Awkward And Weird Truth Or Dare Questions To Ask Your Boyfriend or A Girlfriend You’re Dating

The Embarrassing and Awkward Questions List

To get to know a person well, it is sometimes necessary to touch on sensitive topics and ask uncomfortable or daring questions. For example:

  1. Have you ever suffered from a psychological problem?
  2. Have you ever been unfaithful?
  3. Have you ever kissed someone of the same gender?
  4. Do you have a fetish?
  5. Do you think that onanism is something harmful?
  6. How often do you like to make love?
  7. Have you ever had a blind date?
  8. What part of your body do you like the most?
  9. Do you have any love fantasy?
  10. When you don’t feel like something, do you usually set your limits?
  11. Would you seek help for a love problem?
  12. In bed, what is your favorite position?
  13. Do you like it better without protection?
  14. Have you ever had a threesome?
  15. Would you like to practice any position in bed?
  16. Have you ever shut up a fantasy?
  17. What do you like the most to have done to you during making love?
  18. Would you like to practice your fantasies with me?
  19. What are the erogenous zones that you prefer to be caressed?
  20. What is the most romantic thing for you during making love?
  21. What part of my body do you like the most?
  22. Have you ever ejaculated in your pants?

20 Awkward Questions Girls Are Afraid To Ask Guys

We recommend that before asking an uncomfortable or spicy question to a boy or girl you first start feeling the waters. Start with softer topics and if you see that your interlocutor opens up and is also interested in talking about the topic, you can continue with the spicy questions to get to know each other more also in the intimate aspects.

  1. Do you think size matters?
  2. Do you have any fantasy with me?
  3. In what position would you like to have me?
  4. With what kind of underwear have you imagined me?
  5. Where do you imagine you do it to me?
  6. Would you rather be up or down?
  7. Would you like to do something when you wake up?
  8. What part of my body do you like the most?
  9. Is there a position you would like to try with me?
  10. Can you guess what I’m wearing?
  11. Would you like me to record myself for you?
  12. Have you had erotic dreams?
  13. Did you fantasize about me before we met more?
  14. Do you like massages?
  15. Is there a phrase that turns you on?
  16. Would you like me to dance for you before making love?
  17. What is the most sensitive part of your body?
  18. Do you like kisses on the body?
  19. Would you like to kiss any part of my body?
  20. What part of the body would you like me to caress you?

22 Awkward Questions Guys Are Afraid To Ask Girls

The Physical Embarrassing Questions List

Through the most intimate and private questions you can get to know your boy or girl more and thus build trust between both or both. You can try these questions and adapt the conversation to the reactions and responses of the other person.

  1. Have you been attracted to someone of the same gender?
  2. Have you ever had to fake orgasms?
  3. Would you send me pictures of you without clothes?
  4. Do you have any part of your body operated on?
  5. Would you like to do it from the back?
  6. Do you have any STD?
  7. How many people have you slept with?
  8. How would you rate yourself in bed?
  9. What is the worst crime you have ever committed?
  10. Does size matter to you?
  11. Do you have any paraphilia?
  12. Do you have any hobbies?
  13. Have you ever masturbated?
  14. Are you still a virgin?
  15. At what age did you lose your virginity?
  16. What satisfies you the most?
  17. How much money do you have saved?
  18. Have you ever gotten high?
  19. Are you satisfied in your love life?
  20. Do you practice masturbation frequently?
  21. Have you ever been found stealing?
  22. Have you ever had wet dreams? With who?

100 Most Random Awkward Questions List For Couples In Relationships

Awkward Relationship Questions

 To have a healthy and beneficial relationship, it is essential to work on the trust and intimacy of the couple. It is important that you know each other well and that you know important things about each other such as the following:

  1. What are your goals in a relationship?
  2. Would you like to get married one day?
  3. Do you think the idea of having children? How many?
  4. What things don’t you think of the relationship?
  5. What things would you like to improve in the relationship?
  6. Do you have plans outside of the relationship?
  7. What would be the limits that you would establish in a relationship?
  8. Do you have any conditions to be in a relationship?
  9. What things make you feel comfortable in a relationship?
  10. What things make you feel safe in a relationship?
  11. What things attract you about your partner?
  12. What do you need from me right now?
  13. How do you like to be expressed love?
  14. How do you feel loved?
  15. What things bother you in a relationship?
  16. What are the details that I have with you and do they make you feel loved?
  17. What is love to you?
  18. Do you have any insecurity about relationships?
  19. What is your biggest fear in relationships?
  20. Do I offer you all or most of what you need from a partner?
  21. Would you like to change something in the relationship?
  22. What are the things you enjoy the most about the relationship?
  23. Would you tolerate infidelity?
  24. Which are your career goals?
  25. Do you have any philosophy of life?
  26. Would you like to share something else as a couple?
  27. Where would you like to live?
  28. Do you like the quality of the relationship?
  29. Are you happy with me?
  30. Do you feel free in the relationship?
  31. Do you feel understood in the relationship?
  32. Do you feel that you can express yourself freely in the relationship?
  33. Do you feel safe in the relationship?
  34. What are the dreams in which I, as your partner, can accompany you?
  35. Do you feel that I listen and understand you?
  36. Do you feel full in the relationship?
  37. What is the most important thing in a relationship?
  38. What would you like to change about yourself?
  39. When are you attracted to me?
  40. What do you find most interesting in privacy?
  41. What things bother you about me?
  42. What things make you jealous?
  43. Is there anything about the relationship that makes you feel insecure?
  44. Is it important to you to celebrate the anniversaries in the relationship?
  45. What details do you like to receive in the relationship?
  46. What does it mean for you to be unfaithful?
  47. Do you enjoy sharing with my friends?
  48. Do you enjoy sharing with my family?
  49. Does it hurt you not to have achieved something?
  50. What place do you think is the right place for us to live together?
  51. What do you think we need to consolidate our relationship?
  52. What would be the right house for us to live together?
  53. Would you take a trip without many comforts with me?
  54. How important is money to you?
  55. Do you like the relationship to be public?
  56. Do you like the relationship to be more private?
  57. What do you think of marriage?
  58. What do you think of my family?
  59. What are the happiest memories you have of the relationship?
  60. How do you show jealousy?
  61. What is the most appropriate way for you to resolve conflicts?
  62. Have you ever thought about breaking up?
  63. What do you think is my biggest flaw?
  64. Do any of my flaws make you very uncomfortable?
  65. Do you feel that it helped in your personal growth?
  66. At what times do you prefer to be alone?
  67. What things do you enjoy doing alone?
  68. Is there something that I stopped doing that you liked?
  69. Have you seen positive changes in the relationship?
  70. Have you seen changes that you would like to reverse in the relationship?
  71. What do you think about communication in the relationship?
  72. How would you rate our communication in the relationship?
  73. Is communication with the other’s friends important to you?
  74. What do you think is the best way to handle an economic crisis?
  75. What things do you prefer to be informed about before others?
  76. Do you feel included in my activities?
  77. Are you comfortable with my ideals?
  78. Do you like physical caresses?
  79. What physical caresses do you enjoy the most?
  80. Do you like nicknames in the relationship?
  81. What do you think about emotional expression?
  82. Is there something that has offended you about me and that I did not apologize to you?
  83. Have I ever made you feel guilty?
  84. What do you think about asking for support in relationship conflicts?
  85. What do you think about family reunions?
  86. How do you think family reunions should be?
  87. What do you think about divorces?
  88. How do you like to express love?
  89. When do you feel like I’m not paying attention to you?
  90. What topics are you uncomfortable talking about?
  91. Do you consider important to ask things without assuming them first?
  92. What prejudices are difficult for you to overcome?
  93. Is there something you would like us to experience together?
  94. What do you think about romanticism?
  95. What things do you not like to receive as a gift?
  96. Do you know how important you are to me?
  97. Do I make you feel like a priority in my life?
  98. Do you think that making love is necessary enough in a relationship?
  99. Looking for stability in a relationship?
  100. Are you comfortable with labels in a relationship?

30 How Well Do You Know Me Questions List – Awkward Questions to Ask

In addition, to find out what your partner thinks about you, how he values you and how much he knows you, you can ask him the following questions:

  1. What is the best memory of me that you have so far?
  2. Would you take me on a trip with you and your friends?
  3. Is there something I do that makes you blush?
  4. What is the part of my body that you like the most?
  5. Do you like something about my personality?
  6. Do you think they understand you?
  7. Do you find my tastes interesting?
  8. Do you feel that I have the ability to learn to know you?
  9. Is there something about me that bothers you?
  10. what do you think about me?
  11. How would you take any mistakes that I make?
  12. Do you know what my fears are?
  13. What do you think we have in common?
  14. Do you know what my greatest interest is?
  15. Do you know what things bother me?
  16. What do you think I like the most about you?
  17. Do you know what is my best childhood memory?
  18. Do you know when I prefer to be alone?
  19. Do you remember what things make me feel sad?
  20. Do you know what things I like and what things I don’t get?
  21. Do you know anything that I have skill at?
  22. Do you know what things I am passionate about?
  23. Do you know what kind of clothes I would never wear?
  24. What do you think is my greatest achievement in life?
  25. Do you like the way I kiss you?
  26. What is the best quality I have?
  27. Do you remember what is my biggest weakness?
  28. Do you consider me addicted to something?
  29. Do you know what my opinion is on fidelity?
  30. What attitudes about me make you feel protected?

The above content about awkward questions published at Collaborative Research Group is for informational purposes only and has been developed by referring to reliable sources and recommendations from Experts. We do not have any contact with official entities nor do we intend to replace the information that they emit.


Veronica is a culture reporter at Collaborative Research Group, where she writes about food, fitness, weird stuff on the internet, and, well, just about anything else. She has also covered technology news and has a penchant for smartphone stories. .

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