Questions to ask a guy

50 questions to ask a guy. I broke things down into 5 different stages of a relationship. We’ll cover:

Let’s get to it!

General Questions

Questions to ask a guy

  1. What are your personal goals?
  2. What kind of childhood did you have?
  3. What makes you insecure?
  4. What do you expect from a love relationship?
  5. What’s the one thing you can’t tolerate?
  6. What do you find attractive in a woman?
  7. What expectations do you have of yourself?
  8. What was your most memorable birthday?
  9. Have you ever worn girls clothing?
  10. Who are your family and friends?
  11. What kind of music do you like and which places in the city do you like to go to?
  12. What’s the one thing you can’t live without?
  13. What is your funniest memory of high school?
  14. How do you feel working for (company)?
  15. What’s one item you’ve recently crossed off your bucket list?
  16. If you could describe yourself with one word, which would it be?
  17. What is your favorite food?
  18. What is your favorite character from childhood?
  19. What kind of animal do you love the most?
  20. Would you rather choose fishing or hiking?
  21. Do you believe in God?

First date

Questions to ask a guy

  1. What’s the number one thing that you don’t like about Women?
  2. Do you think that dating is harder or easier with the internet?
  3. Are you intimidated by Women that make more money than you?
  4. Who was your celebrity crush when you were a young child?
  5. Do I make you nervous?
  6. How do you feel around me?
  7. Do you ever lie to get what you want from girls?
  8. What was the first thing that came to your mind the first time you saw me?
  9. Would you rather win 1 million dollars or fall in love?
  10. Do you have any questions for me?
  11. What is your romance spirit animal?

The Trial Period

Questions to ask a guy

Ask these questions and he’ll get the idea.

  1. Do your friends know about me?
  2. Do you want to date other girl’s or do you want to have me?
  3. I’m a lot to handle, are you sure you want to date me?
  4. Would you be jealous if you saw me flirting with another guy?
  5. Do you want to come to hang out with my friends?
  6. Do you mind if I post this picture of us on Instagram?
  7. Can you give me a massage?
  8. If I never talked to you again, how much would you miss me?
  9. What did you think about me on our first date?
  10. Are you surprised that we are still dating?

The Honeymoon Phase:

Questions to ask a guy

Pay close attention to his responses and reactions…

  1. Do you like being with me?
  2. Does your Family know about me?
  3. If you could fly anywhere in the World with me, where would we go?
  4. Why did your last relationship not work out?
  5. Are you afraid that I will break your heart?
  6. Do you ever want to have kids? If so, how many?
  7. Would you rather live in a fancy condo in a major city, or at a ranch on a farm?
  8. Would you still want me if I get old and ugly?
  9. Have I ever done or said anything to upset you?
  10. Do you ever remember your dreams? What are they about?

Seriously Dating:

Questions to ask a guy

  1. Would you like to come over to my parents house for dinner?
  2. Do you have any deeply hidden secrets that you want to tell me?
  3. If we have children, and I love them more than you, can you handle that?
  4. Do you want to take a break from our relationship?
  5. If I moved to a different state for work or school, would you come with me?
  6. If we had to have a long-term relationship for 1 year, would you remain faithful?
  7. Do you understand that If you marry me, you are also marrying my Family?
  8. Would you rather travel the World with me, or with your guy friends?
  9. Are you okay with me having guy friends?
  10. If I were to marry you, what would you expect of me?

Together for Years:

Questions to ask a guy

  1. Are you still satisfied with our relationship?
  2. Over the years, have you ever wanted to give up on our relationship?
  3. 10 years ago, what did you imagine that our lives would be like?
  4. Are you willing to make a change in career, even if it means a change in lifestyle?
  5. Have you ever thought about moving to another state or country?
  6. What is something that is still on your ‘bucket list’? Why haven’t you done it?
  7. If I get very sick, will you take care of me? Or send me away?
  8. Do you find me as attractive as I was when you first met me?
  9. Do you love me now for the same, or for different reasons as before?
  10. If my parents get very sick, will you help me take care of them?

Good Questions to Ask a Guy

    1. What’s one thing you’re really good at cooking?
    2. What’s one thing you wish you were really good at cooking?
    3. What meal is most comforting to you when you’re having a bad day?
    4. How do you know when a woman is flirting with you?
    5. What is something that happened in your life that felt like the worst thing at the time, but was really the best thing in the long run?
    6. What’s your definition of a healthy relationship?
    7. What is one thing you would tell your younger self?
    8. What always makes you feel like a little kid?
    9. If you had to give up one food you love, what would it be?
    10. Who would you haunt if you were a ghost?
    11. Do you think ghosts are real?
    12. If you could be the president of the United States, what is one thing you would do?
    13. What’s your favorite thing to do whenever you’re on vacation?
    14. Would you rather relax on vacation or explore and go on adventures?
    15. Would you rather give up meat or sugar?
    16. If you had to give up cake or cookies, which would you give up?
    17. What do you think is the worst thing about the internet?
    18. What is one thing you wish you could do every morning that you never have time for?
    19. Who is the most important person in your life?
    20. Which movie do you hate that everyone else seems to love?
    21. What are you too old for but still enjoy?
    22. What was fun to do once, but you’ll never do it again?
    23. Do you collect anything?
    24. What’s the most meaningful gift you’ve ever gotten?
    25. What always makes you feel sentimental?
    26. What’s your favorite way to flirt with a woman?
    27. When was the last time a stranger did something really nice for you?
    28. What’s a bad movie that you love even though you know it’s terrible?
    29. What makes you feel positive even when everything is terrible?
    30. What would you do if someone cheated on you?
    31. Have you ever broken someone’s heart?
    32. How do you deal with people you really don’t like?
    33. What have you really wanted to do for a long time but haven’t done yet?
    34. What is the funniest movie you have ever seen?
    35. Do you like Christmas or Halloween more?
    36. How would you define a good person?
    37. Have you ever been addicted to anything?
    38. Why do you think the divorce rate is so high?
    39. What advice do you give friends going through a break up?
    40. Would you rather always be late or always be early?
    41. Which animal are you most afraid of?
    42. What’s one personality trait that’s really important to you in a woman?
    43. What’s one personality trait you can’t stand?
    44. What’s your favorite city?
    45. What’s your favorite place to get takeout from?
    46. Would you rather always be cold or always be hot?
    47. Do you ever sleep naked?
    48. What’s your favorite scent?
    49. Would you ever run a marathon?
    50. If you were in the Olympics, what sport would you play?
    51. Would you rather travel with friends or a significant other?
    52. If you had to pick one charity to donate to, what would it be?
    53. Who would you want to play you in a movie about your life?
    54. Who would you want to play your love interest in a movie about your life?
    55. What do you think is the worst thing about working every day?
    56. What is your biggest regret?
    57. Do you believe in love at first sight?
    58. Is there anything you wish you could change about your family?
    59. What’s the weirdest dream you’ve had recently?
    60. What is the worst lie you ever told a girlfriend?
    61. Can you tell when someone is lying to you?
    62. Do you believe everyone has just one soulmate or multiple soulmates?
    63. Would you rather have the power to be invisible or to read minds?
    64. What is your favorite physical feature about yourself?
    65. Would you rather spend a Saturday night hanging out with a woman or going out with your friends?
    66. What’s your most prized possession from childhood?
    67. What is one thing you hope your mother never finds out about you?
    68. What is the weirdest thing you’ve seen in the news recently?
    69. Where is the strangest place you’ve ever kissed someone?
    70. What do you daydream about every time you’re bored?

Interesting Questions to Ask a Guy

  1. What is something you took for granted in your last relationship?
  2. Has anyone ever walked in on you naked?
  3. How would you describe me to someone who doesn’t know me?
  4. What’s your favorite family memory?
  5. What is one tradition you love the most?
  6. What’s your favorite reality show?
  7. Do you have a favorite Kardashian/Jenner?
  8. If you had to choose, would you rather be a model or an actor?
  9. What did you think was silly until you tried it?
  10. Would you rather go to work early and get out early, or go to work late and get out late?
  11. What New Year’s resolution do you always make?
  12. Are you a spender or a saver?
  13. Where did you learn your favorite hobby?
  14. What is your dream wedding like?
  15. Did you get in trouble a lot in school?
  16. What’s your least favorite thing about technology?
  17. Who do you wish you could trade lives with?
  18. What’s the scariest dream you’ve ever had?
  19. What does your perfect day look like?
  20. What’s the worst job you’ve ever had?
  21. Have you ever dated a coworker?
  22. Would you ever date a boss?
  23. What’s the worst injury you’ve ever had?
  24. How can a woman gain your trust?
  25. How many people have you seriously dated?
  26. Have you ever dated someone your family hated?
  27. What was one time you really stepped out of your comfort zone?
  28. What is your biggest guilty pleasure?
  29. If you were a superhero, what kind of secret identity would you have?
  30. What makes you smile no matter what?

Bonus / Random Questions to Ask a Guy:

  1. What’s on your bucket list?
  2. Which social media do you use the most often?
  3. What kind of music do you like and which places in the city you like to go out?
  4. If you could only eat one food for the rest of your life, what would you choose?
  5. Which fictional character scares you the most and why?
  6. What is your favorite movie of all-time?
  7. What’s your dream job, where he would like to work, and do you have any ambitions for the future?
  8. Do you believe in God? Do you have role models and idols, and who are they?
  9. Is physical appearance the most important?
  10. If you could live anywhere in the world, where would it be?
  11. What is the happiest event of your life?

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