450 Questions to Ask a Guy Over Text [The Go-To Resource]

Texting is a great way to communicate with friends and loved ones, and it can be a great way to get to know someone new. One of the best ways to start a conversation with a guy over text is to ask him questions. Asking questions not only helps break the ice but also helps you learn more about the person you are talking to.

450 Questions to Ask a Guy Over Text:

Questions to Ask a Guy Over Text to See if He Likes You

Asking questions over text can be a great way to gauge a guy’s interest in you. By asking specific questions, you can get a sense of how he feels about you and whether or not he might be interested in pursuing something more.

Avoid asking too many personal or sensitive questions at the very beginning, and try to keep the conversation casual and fun. With the right approach, you can get a better sense of how a guy feels about you and possibly take the next step in your relationship.

  1. Who is an important person in your life and why do they matter to you?
  2. What made you smile today?
  3. What do you find most interesting about me?
  4. Do you find me attractive?
  5. If we could do anything together, what would it be?
  6. Are there any topics you especially like to talk about with me?
  7. What do you think about me?
  8. Is it okay to talk about how I’m feeling with you?
  9. How would you describe how I make you feel?
  10. Would it bother you if I asked to hang out more often than normal friends do?
  11. Do you ever get the impression that we’re connecting on a deeper level than just as friends?
  12. Can I text you anytime or is there a certain period when it’s better to contact you?
  13. What kind of conversations do we have that you enjoy the most?
  14. Do you remember the first thing we talked about when we first met?
  15. How have we grown closer to each other since we first started talking or interacting?
  16. Is there anything special about me that stands out to you compared to other people in your life?
  17. Are there topics we can explore together that we both enjoy?
  18. When something isn’t going well for either of us, can I count on you for support and encouragement during difficult times like these?
  19. Do you feel comfortable sharing stories about yourself with me over text message?
  20. Are there moments that stand out to you where I made an impression on you?
  21. Do you believe I’m capable of making some of your dreams come true?
  22. What would be some activities that we could do together that would help us grow closer over time?
  23. What would you say is the most exciting thing that has happened since we started talking?
  24. How do you think our relationship has changed since we started texting?
  25. How do you feel after our conversations? Do they bring you joy and happiness on the day after?
  26. What is something special we can do together to celebrate special occasions like birthdays, holidays, etc.?
  27. Are there moments from the past when you felt particularly vulnerable or exposed but were still confident enough to tell me about it?
  28. Is there a moment we shared that seemed almost too perfect to be true?
  29. What would you say was the most important piece of advice you ever received from me, and how did it shape your life?
  30. Are there any topics you would particularly like to discuss with me?
  31. How can I make our conversations enjoyable for both of us so that neither of us gets bored or tired?
  32. Do you believe we have something unique between us that can not be repeated or found elsewhere when we communicate with someone else?
  33. What do you value most when you talk to me, and how can I make sure that conversation is satisfying for both of us?
  34. Do you sometimes feel that we could grow closer through our conversations, even though there are still times when things go unsaid?
  35. What is something special that only we share, no matter how small or insignificant it may seem on the surface?
  36. Do you ever feel like we’re communicating on multiple levels that go beyond the spoken word?
  37. Do you sometimes feel like it’s easier for you to express yourself differently when talking with me?
  38. Is there something special between us that we haven’t talked about yet, but could still reveal something unique or meaningful to either or both of us?
  39. Are there common interests or beliefs between us that could be further explored and opened up through conversation?
  40. Do you ever find yourself looking forward to our conversations, and if so, what keeps you coming back each time?
  41. What kind of conversations are most meaningful to you – the ones that revolve around small talk, or the deeper conversations about life, dreams, and relationships?
  42. Has there ever been a conversation between us that has particularly stuck in your mind, and why?
  43. Do our conversations tend to have light-hearted moments, deep insights, or something in between?
  44. What experiences do you think we can share with each other to make us feel more connected?
  45. Have you ever felt seen and understood through our communication in ways you did not expect?
  46. Were there difficult topics that we discussed that we ended up being grateful for?
  47. What do you think makes our conversations meaningful and valuable to both of us?
  48. How did we change and grow with each other throughout our conversations?
  49. What shared moments made you laugh or smile?
  50. Do you smile at my messages or just feel indifferent to them?
  51. Can I text you whenever I want to get in touch, or should I respect your space first before contacting you?
  52. When do you feel happiest while being around me?
  53. What kind of music do you like to listen to when you are around me?
  54. Do you ever catch yourself daydreaming about our future together?
  55. Do I still make you look at me when I walk into a room full of people or does familiarity set in?
  56. Do I touch your heart with even the smallest gesture, or am I just a person like any other to you?
  57. Do you feel comfortable around me when we try new things or take risks together?
  58. Do we have a connection that could last forever?
  59. Do I make your heart beat faster or can you stay calm around me?
  60. What do I do that makes it easy to talk to me?
  61. What would be the one thing that would make our relationship even better than it already is?
  62. Are there moments in which I can tell that you truly understand me and vice versa?
  63. Do I have the ability to make you forget your worries and troubles when we are together?
  64. Is my presence in your life something that brings you joy, or is it just bearable?
  65. Am I someone who listens to you instead of just hearing what you have to say?
  66. What does my presence in your life mean to you and how has it changed over time?
  67. Do we both feel comfortable enough to share our thoughts and feelings openly without fear of arguments or misunderstandings?

Flirty Questions to Ask a Guy Over Text

Flirty questions can be a fun and playful way to connect with a guy over text. Asking flirty questions can help create a playful and flirtatious dynamic, and they can also be a great way to express your interest in a person.

However, it’s important to be mindful of the other person’s comfort level and boundaries when asking flirty questions. It’s also important to remember that not everyone may be comfortable with flirting, so it’s always best to make sure your questions are well-received before proceeding.

  1. What is your idea of a perfect date night?
  2. Are there any special skills you’d like to show me?
  3. Who is someone that always puts a smile on your face whenever they’re around?
  4. What kind of things make your heart beat faster when you think of them when talking to me?
  5. If we could go somewhere together, where would it be and why?
  6. Is there anything special I can do to make your heart flutter?
  7. If you could take me somewhere right now, where would it be?
  8. If we went on a romantic getaway together, where would it be and why?
  9. What kind of activities make the sparks fly between us when we are together?
  10. If I wrote a love poem just for you, would you appreciate it?
  11. Do you miss me as much as I miss you?
  12. What do you think of when you think about me?
  13. If we could have an entire day together, what would be on the agenda?
  14. Are there sweet words that always make your heart beat faster when you hear them?
  15. If I asked you to pick me up for a surprise date at my place, would you come?
  16. Are there compliments that make your heart flutter just hearing them from me?
  17. How can I let you know how much I adore and love having moments with just the two of us?
  18. What makes me different from other girls you have dated so far?
  19. Are there sweet nothings that make us both laugh or smile when mentioned between the two of us?
  20. Do you find it tempting when I take the initiative to start a conversation with you?
  21. What is the one thing I could do right now that would make your day brighter and better than before?
  22. Is there a certain way I can show my affection for you that will give you butterflies in your stomach every time?
  23. What is your favorite thing about spending time with me?
  24. Are there any compliments that come to mind when I’m around you?
  25. How do we get closer even if we communicate through text messages?
  26. How can I let you know how much my feelings for you grow every day without saying too much?
  27. Is there something unique that we do together that no one else can understand the feeling behind it?
  28. How do you feel when I smile at you and make eye contact?
  29. What kind of music do you think would set the mood for a romantic night together?
  30. Is there anything I can do better than anyone else in the world?
  31. When was the last time that just thinking about me made your day better than expected?
  32. How often do you think about me when we’re not together?
  33. Can you think of a reason to come over and see me?
  34. If I asked nicely, would you do something for me?
  35. On a scale of 1-10, how much do you like me right now?
  36. Do I make your heart skip a beat when I talk to you?
  37. Do you think about me as much as I think about you?
  38. Do random thoughts about me ever cross your mind throughout the day?
  39. What kind of music do you like to listen to when we are together?
  40. Are you available for lunch today or are there other plans?  
  41. Do you think this connection between us is gonna last forever?
  42. What kind of surprises do you enjoy receiving from me?
  43. Do you get butterflies in your stomach when I smile at you?
  44. How often have you found yourself daydreaming about us together?
  45. Are there any old memories that make you blush whenever you think about them?
  46. Do you still remember the exact moment when our eyes first met?
  47. How about ditching da plans for tonight and streaming our favorite movie together?
  48. Does it bring a smile to your face when I do something sweet for you?
  49. Am I the only one who notices the fireflies dancing around us whenever we’re together?
  50. If we had all the time in the world, what would we do differently together?
  51. Is it okay for me to think of you every second of every single day?
  52. How can I be sure that you believe in me and trust me to take care of you?
  53. What little gestures make your heart flutter, even if they seem insignificant?
  54. Could it be true that holding hands with me is one thing that always calms you down?
  55. Is there something unique about us that no one else can replicate?
  56. What little things do I do that make sure you know how much I care for you?
  57. How do my smile and eyes captivate you the most when we’re together?
  58. Is my presence enough to make your day better?
  59. Is there anything that I do that warms your heart?
  60. What kind of surprises are most memorable for us when shared? 
  61. How can I help take away some of the stress and worry from your life?
  62. When was the last time I said something that made your heart skip a beat?
  63. When was the last time a text from me made your day brighter than usual?
  64. What traits do you admire about me that could use some more nurturing or growth?
  65. Do little surprises or gestures of love still make your heart flutter?
  66. When was the last time we shared a moment that just felt perfect?
  67. What would be an ideal Sunday afternoon spent between the both of us?

Questions to Ask a Guy Over Text to Make Him Laugh

Asking questions over text can be a great way to get to know someone and keep the conversation going. When it comes to making a guy laugh, it’s important to find the right balance between playful and serious.

Some good strategies include using humor, a playful approach to language, and asking open-ended questions that allow for creative and interesting answers. With the right approach, you can easily make a guy laugh and keep the conversation going over a text message.

  1. Do you like cheesy pickup lines or are they too corny for your taste?
  2. What’s the craziest thing you’ve ever tried?
  3. What is the best joke you know?
  4. What was the last funny movie you watched?
  5. What’s the craziest thing you’ve ever eaten?
  6. What is something really funny to you, but no one else seems to think so?
  7. What’s the best prank you’ve ever pulled?
  8. What was your most embarrassing moment?
  9. Do you have any funny stories about nicknames you or your friends had when you were growing up?
  10. Are there any jokes or one-liners that become uncontrollably hilarious in certain social situations?
  11. What would be the funniest way an animal would communicate completely different from how humans do it?
  12. What was the strangest dream/nightmare you ever had in which nothing made sense at all and yet you could laugh about it?
  13. What is the funniest observation you have made in your life?
  14. When was the last time you had to pull out all the stops to make a situation funny when it wasn’t supposed to be?
  15. What do you think is the funniest genre of music to listen to when you want to cheer up someone in need?
  16. Is there anything unique about your personality or life story that people still laugh at when they hear it?
  17. If animals could talk, which creature do you think could tell the best jokes with their unique voice and mannerisms?
  18. Are there any funny quirks or habits that you possess (or observe) that make you laugh out loud every now and then?
  19. Is there a particular joke or line that had you rolling on the floor laughing, no matter how many times it was repeated?
  20. How do you usually react when something funny happens unexpectedly – do you hold back your laughter or let it out without reservation?
  21. Have there been moments that were too funny not to laugh about, even if it was inappropriate under the circumstances?
  22. Are there any funny stories involving superstitious folk wisdom or urban legends that you have heard over the years that have made you laugh every time?
  23. What do you think is the funniest way someone can give directions without getting lost in translation?
  24. What was the most awkward silence you’ve ever experienced, and how did you eventually manage to break it with a joke?
  25. Do you think a good sense of timing is important in finding humor, even when relying on overused jokes or clichés?

Questions to Ask a Guy Over Text to Start a Conversation

Starting a conversation with a guy over text messages can be a great way to get to know him better and find out if there is a connection. To start a conversation, it’s important to ask open-ended questions that encourage him to share more about himself.

Avoid asking yes or no questions, as these can limit the conversation and make it difficult to keep it going. Instead, try to ask questions that are interesting and engaging and that will allow him to share more about his thoughts, feelings, and experiences.

  1. Do you have any goals you are working toward right now?
  2. What is the best advice you have ever received?
  3. Who was your role model growing up?
  4. What is the craziest thing you have ever done?
  5. How did you spend your last vacation?
  6. What is the most interesting place you have ever visited?
  7. Is there anything that still surprises or scares you after all these years?
  8. How do you usually spend your free time on the weekends?
  9. Have you read a good book lately?
  10. Do you consider yourself an optimist, pessimist, or realist when it comes to life in general?
  11. What is something you are passionate about that not many people know about?
  12. What has been your biggest accomplishment so far?
  13. Do you prefer the city or nature for a day trip outing?
  14. What helps you relax after a long day at work or school?
  15. Do you think it’s important to find your purpose in life?
  16. What color best describes your personality and why?
  17. What have you always wanted to do but have not yet?
  18. What can someone do to make themselves stand out from the crowd?
  19. Is there something that others may see as a negative quality about you that you find admirable instead?
  20. What is one area in your life that you feel you could use more help or advice with right now?
  21. What was the last movie you watched and what is it about?
  22. If you could pick any place in the world, where would you go right now?
  23. Do you prefer dogs or cats, and why?
  24. If a genie granted you 3 wishes, what would they be?
  25. Are there any topics or interests that you’re passionate about?
  26. Are there any special skills or talents that set you apart from others your age?
  27. Are there any new skills or topics that you’re interested in learning about lately?
  28. Do you enjoy learning new skills and knowledge?
  29. Are there any new activities or hobbies you’ve been wanting to try?
  30. Do you have any exciting plans for the future?
  31. Do you have anything fun or exciting planned for this weekend?
  32. What do you like to do in your free time?
  33. Are there any interesting stories from your childhood that you can tell?
  34. What kind of music do you listen to when you’re in a good mood?
  35. Is there something that someone recently said that left a lasting impression on you?
  36. What is something that really excites you right now?
  37. If you could choose anything, what would be your dream job?
  38. What are some of your favorite places to hang out with your friends?
  39. If you could be magically transported to any place in the world, where would you go and why?
  40. Who are some of the people who have had a big impact on who you are today?
  41. What is something you are most proud of and why?
  42.  Is there a certain type of music that helps you toward personal growth and why?
  43. If money were no object, what dream would you pursue first?
  44. What has been the most important moment in your life so far and why?
  45. Do you have any personal growth goals that you are currently working on achieving?
  46. Are there certain values that guide your life choices and why are they important to you?
  47. Are there any upcoming events or concerts that you are looking forward to?
  48. Do you prefer to stay home or go out when you meet with friends?
  49. Are there any significant experiences or life lessons that have shaped who you are today?
  50. If someone gave you a blank check right now, what would you do with it first?
  51. Do you have any favorite books, podcasts, or TV shows?
  52. What do you find most inspiring in life?
  53. Are there any causes or issues that are important to you?
  54. What would your ideal weekend look like?
  55. Who are some of your favorite people to follow online?
  56. Do you prefer to be in the city or out in nature?
  57. Is there something that always brings a smile to your face when you think about it?
  58. Who is the most special person in your life?
  59. Do you prefer salty or sweet snacks?
  60. Do you prefer summer or winter?
  61. Are there any special places you’d like to visit someday?
  62. When was the last time you laughed out loud at something funny?
  63. What’s the best concert you have ever seen live?
  64. How many times a day do you check your phone, roughly?
  65. If something strange happened in your neighborhood, who would be the first person you would think of to investigate it with you?
  66. Is there anything exciting on your agenda this weekend?
  67. What top three items would you choose from to create your dream breakfast brunch if you had free choice in ingredients and preparation method?
  68. Is there an upcoming event, either online or virtual/in person, that has caught your attention and piqued your interest lately?
  69. If you could ask a celebrity one question, what would it be?
  70. What kind of challenges do you face most often?
  71. What would make you laugh uncontrollably right now?
  72. Do you prefer formal or informal dinners?
  73. Do you have any rituals that help you stay focused or relaxed throughout the day?
  74. What do you think makes someone interesting and intriguing?
  75. What nostalgic memory from your childhood still brings a smile to your face when you think about it today?
  76. What is your favorite form of self-expression?
  77. Are there controversial topics that you have passionate conversations about with other people?
  78. What motivates you and drives you to keep going and achieve your goals?
  79. Do you believe that small changes in your life can lead to big results over time?
  80. Is there anything in your life that you still feel a deep passion for, regardless of outside influences or views that exist or have existed about it?
  81. Are there activities that you inherently prefer to do over others, and why is that?
  82. Do you feel that there is something special, perhaps even magical, about life itself – if so, what is that according to your interpretation of the subject?
  83. Do you believe that people should keep certain things to themselves, or should they talk openly about everything, no matter what?
  84. Do you think intelligence has more to do with nature or nurture?
  85. Is there a cause you are passionate about and why is it so important to you?
  86. Are there common misconceptions about you that you would like to dispel once and for all?
  87. Do you believe in fate, or do we choose our own path and determine our own destiny?
  88. Is there a particular artist, musician, or another creative person who has inspired you in some way recently, and why is that, in terms of their work ethic, talents, craftsmanship, public appearance, etc.?
  89. If you could describe today in just one color, what hue might that be exactly?
  90. What challenges do you typically encounter during the day and how do you deal with them?
  91. What is something unique about you that others may not know at first glance, and that you may want them to take time to figure out, etc.?
  92. Is there a particular hobby that helps you develop new ideas or perspectives on some of the projects you are working on?
  93. How long have you been working on your current artistic/creative project, and what has been your experience with it so far?
  94. Do you prefer to work alone or in collaboration with others when tackling creative projects or tasks?
  95. When was the last time you took a risk and what impact did it have on your life?
  96. What type of creative environment do you prefer to work in when creating something, e.g. music, art, film, etc.?
  97. Are there any lessons you have learned along your creative journey that can be applied to other aspects of life?
  98. When was the last time that something surprised you about yourself and why was it surprising to you, especially in terms of time and circumstance?

Deep Questions to Ask a Guy Over Text

Asking deep, thought-provoking questions over text can be a great way to get to know someone on a deeper level and understand their values, beliefs, and aspirations. When asking a guy deep questions over text, it’s important to find the right balance between curiosity and respect for his boundaries.

Avoid asking overly personal or intrusive questions. Instead, focus on asking questions that will get him thinking about his life, values, and beliefs. Be open-minded and non-judgmental when asking deep questions, and be willing to share your own thoughts and perspectives as well.

  1. What makes you feel most alive?
  2. What is the importance of family to you?
  3. What is something that really scares you but also interests you?
  4. What do you believe makes a successful relationship?
  5. How have your experiences shaped the person you are today?
  6. Do you have any irrational fears or superstitions?
  7. Are there any life lessons that have had a particularly strong influence on who you are as a person today?
  8. How would you describe your current mindset or outlook on life compared to the past?
  9. Do believe people change or stay the same over time in terms of their beliefs, values, and personalities?
  10. Would it be worth sacrificing certain things to achieve success?
  11. Do you have personal beliefs that you would never compromise on?
  12. Is there anything that would make you more satisfied with life?
  13. Are there any hopes or dreams that motivate you in life?
  14. How important are relationships to your overall well-being and happiness?
  15. How can you stay mindful when you’re surrounded by so much noise and distractions in today’s world?
  16. When should you take a risk?
  17. Are humans capable of making independent decisions?
  18. Was luck a factor in achieving the status we have today?
  19. Are the values of a generation still relevant?
  20. Should the use of social media be limited?
  21. What do you think are the most important values to live a fulfilling life?
  22. Are feelings always an indication of what is right or wrong for us?
  23. Is it better to live life with low expectations or high hopes?
  24. How can we promote inner peace and stillness in our lives?
  25. Would it ever be possible to fully understand someone if their experiences were different from ours?
  26. Are dreams an indication of the truth of our subconscious mind or just random thoughts in our sleep?
  27. Is it possible to stay motivated while overcoming personal obstacles?
  28. How do emotions affect our judgment of other people’s actions?
  29. Can we learn anything from the mistakes of others, even if there is no direct connection between the two of us?
  30. Can determination alone bring us closer to achieving goals, without outside help or support?
  31. Do you think it’s possible to truly know someone without knowing their history?
  32. Is there something from your past that still affects how you think today?
  33. Do you think it’s possible to challenge yourself and grow without taking risks?
  34. Are there any personal experiences that have changed your outlook on life?
  35. Are there lessons you have learned from failures that stayed with you?
  36. Do you believe in second chances, and why or why not?
  37. How would you define true happiness for yourself?
  38. What do you think is life’s greatest lesson, if any?
  39. How do you see the world differently than most?
  40. Is there something from your past that still haunts you today?
  41. What’s one core value that guides you in all of your choices and decisions in life?
  42. Can you recall a time when taking a risk paid off for you?
  43. Has anyone ever challenged their preconceived notions about you as a person?
  44. What do you think is the real power behind building meaningful connections with others?
  45. Do you believe it’s possible to start from scratch and begin a new life for yourself?
  46. Are there moments of disbelief that have left a lasting impact on your understanding of reality?
  47. How have your past experiences shaped the way you view things today?
  48. What do you think is the key to finding true success in life?
  49. What do you think about failure and how does it affect you?
  50. Is there anything you believe should never be compromised no matter what the situation is?
  51. Do you ever catch yourself searching for answers to age-old questions like “who am I” or “why am I here“?
  52. Do you believe that our lives are ultimately determined by fate, destiny, or free will?
  53. How do you define courage and when have you found yourself needing it most in life?
  54. If you had one wish to change the world, what would it be?
  55. Do you think it is possible to find true love and genuine happiness with another person?
  56. How do you think our society should deal with controversial issues such as racism and sexism?
  57. How do most people make judgments about right from wrong – based on morality or practical considerations?
  58. If you could give your younger self one piece of advice, what would it be?
  59. How important is it to you to make a difference in the lives of others?
  60. Do you feel that holding on to resentment or grievances does more harm than good?
  61. If you could erase one bad memory from your life, what would it be?
  62. Where do you see yourself in five years and what steps are you taking to get there?
  63. Are there any experiences that have opened your eyes to see the world differently, and if so, which ones?
  64. Do you think that empathy is an important quality for people to have, and why or why not?
  65. Do you believe in miracles or the power of prayer?
  66. Are there any decisions you always question or regret, and why?
  67. What do you think makes up a person’s character?
  68. What small act of kindness have you done that had a big impact on someone else’s life?
  69. Do you think it is ever beneficial to keep secrets, even if they are from close family members and friends?
  70. How has your opinion of yourself changed over time and why?
  71. What do you think are the causes of some of the problems and injustices in the world?
  72. Do you believe in karma, and what role has it played in your life?
  73. What types of activities give your life purpose and significance?
  74. Have you ever had experiences that caused you to reevaluate your core beliefs or values?
  75. Do you believe that people are capable of changing for the better, and why or why not?
  76. What kind of lifestyle choices do you think lead to lasting happiness for yourself and those around you?
  77. Are there any difficult lessons that have taught you valuable life skills, such as resilience or patience?
  78. What do you think is the best decision you have made in life so far, and why?
  79. What makes someone truly beautiful to you?
  80. Do you feel that time can heal all wounds, or can they last forever?
  81. What basic message or lesson did you learn from your parents as a child?
  82. Do you have a purpose greater than yourself that guides your actions every day?
  83. Are there moments that remind you of how precious life can be?
  84. What would you change about yourself if given the chance?
  85. What do you think is the secret to true love?
  86. If you could tell your younger self anything, what would it be?
  87. Do you believe in fate or that everything happens for a reason?
  88. Was there ever a time when you felt like giving up, and why?
  89. How do you decide which path to take when faced with difficult choices?
  90. Do appearances sometimes deceive us when it comes to judging a person’s character?
  91. What are things that bring out the best version of yourself?
  92. Do chances come around more than once in life, or should we seize them while they are there?
  93. What is one thing that everyone should experience at least once in their life?

Awkward Questions to Ask a Guy Over Text

Asking questions over text can be a great way to get to know someone, but it can also be difficult to navigate. It’s important to keep in mind that some questions may be perceived as awkward or inappropriate. It’s important to be considerate of the other person’s feelings and boundaries and to avoid asking personal or sensitive questions without first building a rapport.

  1. Did you miss me?
  2. Are you still friends with your ex?
  3. Do you still have feelings for your ex?
  4. Are you attracted to me?
  5. How much do you make each year?
  6. Have you ever gone to therapy?
  7. What family background do you come from?
  8. Could you imagine breaking up with me over text or email?
  9. Is there anything that makes us incompatible as a couple?
  10. What would be your first reaction if I asked you to marry me?
  11. What’s the strangest thing you’ve ever done?
  12. Have you ever sneezed in front of someone and then it sounded like something else?
  13. What was the worst hairstyle decision you ever made?
  14. Are there any embarrassing photos of you floating around the internet somewhere?
  15. Are there any words or phrases that make others cringe when they hear them come out of your mouth because they’re associated with past experiences or memories?
  16. Have you ever tried to make someone laugh with a joke but were met with complete silence instead?
  17. What embarrassing or awkward nickname did you have in school or childhood that people still call you?
  18. What was the most awkward comment someone has ever made to you directly or in front of a group of people that left you completely speechless?
  19. What is the most embarrassing thing you have ever done?
  20. What is your most embarrassing memory?
  21. What’s the worst date you’ve ever been on?
  22. What do you do when no one else is around that people might find strange?
  23. Have you ever had a dream where you showed up at school or work without any clothes on?
  24. Have you ever been arrested?
  25. Do you think any of your past relationships were bad decisions, and why or why not?
  26. Why are not you answering my calls/texts/emails?
  27. Are our conversations boring for you?
  28. Do you talk to other girls more than you talk to me?
  29. Do my friends annoy you when they hang out with us?
  30. Do I smell bad to you?
  31. Why have not you asked me out on a date yet?
  32. Do you have any debts?
  33. Have you ever been fired from your job?
  34. Have you ever been to jail?
  35. Do you have a criminal history?
  36. Do you have any mental health issues?
  37. Am I taking up too much of your time?
  38. Does my appearance sometimes make you jealous?
  39. Does my personality annoy or offend you in any way?
  40. Are my expectations impossible to meet?
  41. How often do you take a shower?
  42. Would I get along with your friends and family if we dated?
  43. Do I talk too much?
  44. Do you have any dark secrets I should know about?
  45. What would you like me to do if I were to come over now?
  46. Is there anyone else that you are interested in right now?
  47. What is your financial status like?
  48. Have you ever been in a cult?
  49. Why don’t you ever want to spend time with me?
  50. How often do you check your ex’s social media?

Truth or Dare Questions to Ask a Guy Over Text

Truth or dare questions can be a fun way to break the ice and get to know a guy over a text. These types of questions can range from lighthearted and playful to more serious and personal. They can spark a conversation, bring hidden truths to light, or challenge the other person to take a risk. The important thing is to ask the questions appropriately and respectfully and be prepared to answer them.

  1. Have you ever taken something that did not belong to you?
  2. Who was your first crush?
  3. What’s the craziest thing you have ever done?
  4. What secrets have you never told anyone?
  5. What do you think of when no one is around?
  6. When was the last time you lied and why?
  7. If money were no object, what would be your dream job?
  8. What is the most embarrassing thing that has ever happened to you in public?
  9. Are there any dark secrets from your past that still haunt you today?
  10. Would you rather tell someone a harsh truth or lie to them for their own good?
  11. If you could take one item from this room and keep it to yourself, what would it be and why?
  12. Have you ever cheated on someone, either emotionally or physically?
  13. Are there any embarrassing moments that you still cringe at when you think about them today?
  14. What is the craziest thing you would do for a friend?
  15. Who was your first kiss and where did it happen?
  16. Have you ever cheated on a test?
  17. Have you ever had a crush on a friend’s partner?
  18. Have you ever been in love with someone who didn’t love you back?
  19. Have you ever been involved in a physical fight?
  20. When was the last time you lied and why?
  21. Have you ever had to apologize for saying or doing something mean to someone?
  22. What do your friends think about you that is not true at all?
  23. What’s the craziest thing you have done on a dare?
  24. What is one thing you would not do under any circumstances?
  25. What was the craziest plan you made but never carried out?
  26. Have you ever told a white lie to get out of trouble?
  27. Have you ever stolen something from someone?
  28. Is there something embarrassing you want to confess to the group?
  29. Have you ever broken someone’s trust?
  30. Have you ever felt betrayed by someone close to you?
  31. What do you regret not doing during your school years?
  32. Have you ever been on a blind date?
  33. Who would you want to be stranded on an island with?
  34. If you had the chance, would you want to live forever?
  35. What do your friends think is your best quality?
  36. If you had the chance, would you parachute out of a plane?
  37. If you only had one day to live, how would you spend it?
  38. Would you rather be famous for one day and then be forgotten, or remain unknown forever?
  39. What is the worst decision you’ve ever made, and what did you learn from it?
  40. What is the most embarrassing thing that has ever happened to you in public?
  41. If you could do one thing differently in life, what would it be and why?
  42. What is the craziest thing you have done in search of an adventure?
  43. What would you do if you won the lottery?
  44. Do you have any weird habits?
  45. What is your guilty pleasure?
  46. What is the strangest dream you have ever had?
  47. Have you ever broken rules for fun?
  48. What is the craziest thing you have ever done for love?
  49. What is one thing you can do better than anyone else?
  50. What has been your greatest epiphany in life so far?

Frequently Asked Questions

How Can I Keep a Conversation Going With a Guy Over Text?

To keep a conversation going with a guy over text message, try asking him open-ended questions that encourage him to tell you more about himself. Also, respond to what he says and ask follow-up questions to show that you are actively listening and interested in what he has to say. Also, share something about yourself in each message to keep the conversation flowing.

Is It Okay to Text a Guy First?

Yes, it’s perfectly okay to text a guy first. It can even be a good way to initiate a conversation and show that you’re interested in him. Just be aware that he may not always respond right away, and it’s important to respect his boundaries and give him space when he needs it.

What Should I Do if a Guy Doesn’t Text Me Back?

When a guy doesn’t text you back, it’s best to give him some space and not take it personally. Maybe he’s busy or has something else going on in his life. If you’re really interested in him, you can try writing him again a few days later or asking if everything is okay. But it’s important to remember that not everyone is going to be interested in communicating with you, and that’s okay.

How Often Should I Text a Guy?

The frequency of text messaging should be comfortable for both parties. It’s important not to overwhelm the other person with too many messages. It’s a good idea to wait for the guy to respond before sending another message, and to respect his communication style and boundaries.

How Can I Make a Good Impression Through Text?

To make a good impression through text, it’s important to use proper grammar and spelling and to be respectful and considerate in your messages. Also, try to be interesting and engaging by asking open-ended questions and sharing information about yourself. Avoid using too many emojis or slang, as these can be perceived as unprofessional. Also, be mindful of your tone and make sure your messages come across as friendly and positive.


Asking questions over text is a great way to get to know a new person and build a deeper connection. Whether you are looking for a new friend or a romantic partner, taking the time to ask thoughtful and interesting questions can open up the conversation and help you learn more about the person you are talking to. Remember that it’s also important to actively listen and respond to what the other person is saying, as well as share some personal information about yourself.

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