1. What is one thing that brings a smile to your face, no matter the time of day?
2. What’s is one thing that you’re proud of?
3. What makes you laugh?
4. When you’re feeling super lazy, what’s your guilty-pleasure Netflix show?
5. What’s the scariest thing you’ve ever done?
6. What is one memory you have from childhood?
7. What’s the best thing about your life right now?
8. What is one thing that you’re thankful for?
9. What’s one thing that you fear?
10. If you could only watch one movie for the rest of your life, what would it be?
11. Can you tell me one thing, big or small, that you’ve never told anyone else?
12. If you were forced to leave your home and move to a county you’ve never been before, what are three things that you’d take with you?
13. What’s a favorite memory with a pet/animal?
14. Who are you closest to in your family?
15. What’s your family like?
16. What’s your favorite flavor of ice cream?
17. What’s your favorite joke?
18. What’s the stupidest thing you’ve ever done?
19. If you could rewrite your past, what’s one thing you’d change?
20. What do you think your best physical feature is?
21. What’s one thing about yourself, personality-wise, that you like?
22. When you’re feeling down, who or what is your biggest go-to person or activity?
23. If you could only eat one food for the rest of your life, what would it be?
24. What’s one thing you’re super passionate about?
25. If you had to lose one of your five senses, which would you give up and why?
26. What’s the hardest thing, physically, you’ve ever done?
27. What’s the hardest thing, mentally, you’ve ever done or been through?
28. What’s the best part about your job?
29. What’s one thing that defines who you are?
30. If tomorrow was your last day on earth, what would you do in your last 24 hours?
31. What do you believe in, generally or faith-wise?
32. If you had to describe yourself in three words, what would they be?
33. Where’s the coolest place you’ve ever been/traveled to?
34. What’s one thing people would never know about you just by looking at you?
35. What’s one thing about the opposite sex that you’re attracted to?
36. What are three qualities you look for in a potential date?
37. What’s the sweetest thing you’ve ever done for a girl?
38. How would others describe you?
39. What’s your all-time favorite memory?
40. What are your parents/step-parents/guardians/people who raised you like?
41. What’s your go-to alcoholic drink?
42. What would be your ideal first date?
43. If you could have three wishes, what would they be?
44. If you could a full 24 hours without any work or obligations, a day to just do whatever you wanted, what would you do?
45. What is the best compliment you’ve ever received?
46. What is something you’re talented at?
47. What’s your favorite college memory?
48. What is your best friend like?
49. If you could live anywhere in the world, where would you live?
50. What’s one thing you want to do before you die?
51. If someone gave you a million dollars right now, what would you spend it on?
52. Have you ever made a decision that changed your entire life? If so, what was it?
53. What’s your favorite thing to do on the weekends?
54. What’s your zodiac sign? And do you think it describes you?
55. What’s your biggest regret?
56. What can always put you in a good mood?
57. What’s your guilty pleasure snack, drink, or junk food?
58. If you were forced to eat fast food for your every meal, what would be your top two places?
59. What’s one thing you wish you could change about yourself?
60. If you had the option to hit restart and begin life all over again, would you?
61. Have you ever lost someone close to you? What were they like?
62. What’s your favorite social media profile?
63. What’s one thing that totally relaxes you when you’re stressed?
64. What’s a random hobby you’ve always wanted to try but never have?
65. When was the last time you cried, and why did you?
66. What scares you the most about the future?
67. Do you want to have children someday?
68. What do you imagine your future family will be like?
69. Have you ever done or accomplished something you never thought you could? What was it?
70. What’s one thing you could never live without?
71. Who is one person you could never live without?
72. What’s your favorite vacation place?
73. Would you rather go out or stay in on a Saturday night?
74. What’s your favorite quote, line of poetry, or sentence?
75. What’s your favorite family memory?
76. What’s one thing that helps you decide you can trust someone?
77. Have you been in love before?
78. How would you explain what ‘love’ is?
79. Have you ever gotten your heart broken?
80. What’s one thing you’ve learned about yourself from a past relationship?
81. What’s your biggest pet peeve?
82. What’s one thing that’s a total turn off?
83. What’s one thing that’s a total turn on?
84. What’s the craziest thing you’ve ever done for a girl?
85. What’s your go-to drink/food/activity when you’re sick and in bed?
86. What’s the scariest thing that ever happened to you as a kid?
87. Who in your family, immediate or extended, are you the most similar to?
88. Where do you see yourself in five years?
89. What’s your favorite song or artist?
90. What would be your dream job?
91. If you were writing a book about your life, what would the title be?
92. What’s your favorite word?
93. What keeps you up at night?
94. What’s your go-to phrase?
95. What’s one silly, little-kid item that you still have somewhere hidden in your room?
96. Who is someone that’s impacted your life or helped you become who you are?
97. What’s one thing you want to achieve before you die?
98. What’s your favorite book?
99. What’s one thing, silly or serious, that you’re guilty of?
100. What makes you blissfully, completely, smile-from-ear-to-ear happy?
Bonus: 100 Questions To Ask A Guy If You Want To Know Who He Really Is
1. What was your childhood like?
2. Did you have a close bond with your parents?
3. Do you have any brothers or sisters?
4. What was your first crush like?
5. Are you still friends with your exes?
6. If you had to describe your father, what would you tell me about him?
7. What was your biggest achievement?
8. Do you like animals?
9. What’s your favourite song from your teenage years?
10. What makes you feel happy?
11. Are you a competitive person?
12. Do you like any sports?
13. What’s your favourite book?
14. Would you lend it to me?
15. What do you think about death?
16. What about children?
17. What is your favourite memory from childhood?
18. What is your favourite scent?
19. How did you lose your virginity?
20. What’s your strongest character trait?
21. What is your weakest spot?
22. Do you consider getting married one day?
23. What do you think about Pink Floyd?
24. How do you like to dance?
25. What is your favourite album?
26. What was the worst winter of your life?
27. On a scale from 1 to 10, how good would you say you are at singing in public?
28. Are you left wing or right wing? Or in between?
29. Are you pro choice or pro life?
30. Have you ever felt attracted to a queer person?
31. Did you ever participate in a protest?
32. Would you date two girls in the same day?
33. Would you ever date a blind person?
34. Tell me about the one who got away.
35. How many pairs of shoes do you have?
36. Do you own a suit?
37. Have you ever stalked someone?
38. What’s the biggest life lesson you have learned?
39. What’s the most significant love lesson you have learned?
40. What is your favourite summer memory?
41. What is it about us girls that makes you so horny?
42. What was the biggest letdown of your life?
43. What would you take with you on a deserted island?
44. What would you say about your relationship with God?
45. Tell me about the worst job you’ve ever had.
46. What are you most ashamed of?
47. What are you most proud about?
48. How would you rate today’s politics in terms of efficiency and protection?
49. Do you wish you were born some place else?
50. What are you secretly fond of?
51. What’s the most important quality you enjoy in a friend?
52. Did you ever betray anyone you loved?
53. If I gave you a pen and paper what would you make out of them?
54. What’s the movie scene you loved the most?
55. How do you relate to people who suffer from mental disorders?
56. What is your opinion on men who refuse to use condoms?
57. What are some of the things you wish a girl knew before dating you?
58. Are you a feminist?
59. What is your take on climate change?
60. What are your top 3 healthy habits?
61. What do you think about psychology and what role did it play in your life?
61. Tell me the most embarrassing experience you had in bed.
62. Would you date someone who doesn’t have any books in their house?
63. What do you love most about travel?
64. What’s the best thing about being single?
65. Do you believe in astrology?
66. Have you ever went and kissed a total stranger out of the blue just because you could not resist it?
67. What is your most treasured memory?
68. What makes you laugh?
69. What are you still sad about?
70. How would you handle someone hitting on your significant other?
71. What are your feelings towards open relationships?
72. Have you ever been jealous?
73. Where do you see yourself in the year 2050?
74. Do you believe everyone we meet is meant to teach us a lesson about ourselves?
75. Have you ever walked away from someone you still loved?
76. What’s your to go place when you’re having a bad day?
77. Can you make pancakes?
78. Would you make breakfast in bed for a girl you fancy?
79. What do your friends say about you?
80. What are your most beloved artists, and why?
81. Where should I go if I want to spend my day as a tourist in this city?
82. What’s your favourite piece of art?
83. Have you ever had sex in a forbidden place?
84. What do you love most about sleeping with a girl?
85. What are your mornings like?
86. What is your favourite drink?
87. Where would you go if you only had 24 hours to live?
88. What’s the best thing about being single and happy?
89. What’s the best advice someone has ever given to you?
90. What would you tell your teenage self if you could send them some insights from the future?
91. Do you believe in miracles?
92. Are you fond of who you are?
93. If you had to describe the most intense moment of your life using only one word, how would you name it?
94. What makes you sad?
95. Where would you like to spend the rest of your life if you could?
96. Would you give away everything you had if you were promised to be forever young?
97. What is something you’ll never apologise for?
98. What is the first thing you notice about a woman?
99. Have you ever been in love?
100. Will you kiss me now?
Bonus: 50 MORE Questions To Ask A Guy If You Want To Know Who He Really Is
1. If you could go anywhere in the world, where would you go and why?
2. Are you a morning person or night person?
3. Do you prefer making plans or following along with what someone else planned?
4. Do you have a mentor in life that you’ve continuously looked up to?
5. When do you feel most vulnerable?
6. Where is the one place you’ve lived that has actually felt like home?
7. If you could change anything about yourself, what would it be and why?
8. What are you most proud of accomplishing?
9. What would your dream vacation consist of if money wasn’t a factor?
10. Can you honestly say you love what you do everyday?
11. What is one thing in life that makes you feel alive?
12. Are you a cat person or a dog person?
13. If you could change one thing about the world what would it be and why?
14. If you won the lottery what is the first thing you’d do with your money?
15. If you could go back and redo a part of your life, would you?
16. If you could go back and pick a different profession, what would you choose?
17. If you could live anywhere in the world where you would move?
18. Who in your life do you admire the most?
19. If you were a woman for a day what is the first thing you’d do?
20. What is your favorite hobby?
21. How often do you read your Horoscope?
22. What are the top three things on your bucket list?
23. Are you more of a summer or winter kind of person?
24. What helps you unwind after a long, stressful day?
25. When you’re upset do you like to be comforted or left alone?
26. If you could change your name, what would you make it and why?
27. What was the best day of your life thus far?
28. What was the happiest moment you’ve ever experienced?
29. Do you feel like something is missing from your life?
30. What are you most passionate about?
31. What is one thing you’d love the learn more about?
32. What is your favorite non-physical part about yourself?
33. What is more important to you: money or happiness?
34. What was the last thing to make you cry?
35. What is your biggest fear?
36. What is the craziest thing you’ve ever done?
37. What is your biggest pet peeve?
38. What would you consider your best trait? And your worst trait?
39. What is the first thing you notice when you meet a girl?
40. Have you had any near death experiences?
41. What is the one thing that can always make you smile?
42. If you could marry one fictional character or celebrity, who would it be and why?
43. What is better in your opinion – asking for forgiveness or permission?
44. What is the most embarrassing moment you’ve ever experienced?
45. Would you rather watch the movie or read the book?
46. If you could have one super power what would it be and why?
47. How do you deal with people in your life who you don’t like?
48. What is your biggest regret so far?
49. Have you ever got in trouble with the law? If so, what for?
50. If you could go back to a certain time in your life, what would it be?