The Ultimate List: 111 Questions to Ask a Guy on the First Date

The dating game is probably the most thrilling one of them all, but you surely know how hard it can be to hit it off with someone on the first date. Things can get awkward, neither of you is sure what would be appropriate to ask and what not, one might be afraid that the other one will be scared off … or you're just a bit shy.

That can happen easily to anyone and actually even if you are going on the first date with someone that is not a complete stranger, it can be tough. So, it's safe to say first dates are intimidating (see, even that says “dating”!).

How to ensure you won't mess it up and will have an awesome second date as well?

There are some foolproof questions that will help you out and we have gathered some of these ideas on this epic list. All of these questions are completely safe to ask on the first date and won't bring any compromising situations or awkward silences.

Of course, don't ask these like your life depends on it or like he is a contestant on the “Who Wants To Be A Millionaire?”, but you can get the conversation started with these easily and hopefully get the ball rolling!

PS: We have left out questions regarding politics and exes – these are the grey areas that are likely to cause tension and not in a fun way. First dates should generally be kinda light and casual, so deeper relationship topics should be left out of the first date. Scroll to the bottom of the post to see some of those questions we think you should avoid on the first date.

111 best questions to ask from a guy on the first date:

1. When is your birthday?
2. Do you have any nicknames?
3. How many siblings do you have?
4. What’s the most spontaneous thing you’ve ever done?
5. What’s your ideal vacation?
6. What’s the luckiest thing that’s ever happened to you?
7. What is your biggest pet peeve?
8. What was the worst job you’ve ever had?
9. What are you passionate about?
10. What is your favorite movie genre?
11. Are you a cat person or a dog person? Or both?
12. Coke or Pepsi? Tea or Coffee?
13. What's your favorite holiday?
14. Ever went on a road trip?
15. What is your favorite food?
16. Do you like to dance?
17. What is your favorite Disney movie?
18. Are you a collector of anything?
19. What's your favorite thing to do on a Sunday afternoon?
20. What is your favorite book?
21. What are some things about you that you take pride in?
22. If you could have a superpower, what would that be?
23. What kind of music do you like?
24. What do you see yourself doing with your life in 5 years, 10 years?
25. What is the weirdest thing about you to most people?
26. What was your first kiss like?
27. What is your dream job?
28. Do you believe in soul mates?
29. Are you willing to stay away from your family if you ever have to for a job?
30. What's your favorite color?
31. What are the 3 things you dislike the most?
32. Have you ever experimented with drugs?
33. If you had three wishes, what would you wish for?
34. If your house was on fire and you could save one possession, what would you save?
35. Favorite quote in life?
36. Beach holiday or sightseeing holiday? Why?
37. If your life were a book, what would you name it?
38. How much TV do you watch?
39. Would you like to be famous?
40. What do you value most in a friendship?
41. How did you celebrate last Halloween?
42. Do you subscribe to any magazines?
43. What's your favorite drink?
44. Where did you go to school?
45. If you could only eat one thing for the rest of your life, what would it be?
46. What's on your bucket list?
47. Are you a night owl or a morning person?
48. Do you cook?
49. Who did you want to become as a little boy?
50. Who has been the biggest influence in your life?
51. What’s your favorite place in the entire world?
52. Have you ever kept a New Year’s resolution?
53. If you could live in any other U.S. city, which city would you live in?
54. What was your favorite subject in school?
55. What do you think is your greatest strength?
56. What’s the scariest thing you’ve ever done?
57. What’s one bad habit you would like to break?
58. If you could visit any time period in all of history, what would it be?
59. What countries have you visited?
60. Who are you the closest to, in your family?
61. What is the first thing you do when you head back home from work?
62. What is the naughtiest thing you have done as a child?
63. How did you meet your best friend?
64. What is something you’ve always wanted to try but have been too scared to?
65. Do you have a sweet tooth or a savory tooth?
66. What is your favorite YouTube channel?
67. What motivates you?
68. What kind of phone was your first cell phone?
69. Do you have any strange talents?
70. What’s your favorite cheesy pick-up line?
71. Who is a character from a TV show or a book that you’ve always resonated with?
72. What would you do if you won a major lottery?
73. Do you believe in any superstitions?
74. What is your most frequented Web site?
75. If you wrote a book, what would it be about?
76. Would you rather never have to clean the kitchen again, or never have to clean the bathroom again?
77. Would you rather live in a hot country or a colder climate?
78. What’s your favorite physical feature of your own?
79. Did you like high school or college better?
80. What was the best party you ever went to?
81. Which would you like most: a summer house, a year-long vacation, or a boat?
82. Are you an optimist, a pessimist, or a realist?
83. As a teenager, did you ever rebel against your parents?
84. Did you ever want more or fewer siblings?
85. What is your most unique trait?
86. What is your favorite gaming platform?
87. Are you allergic to anything?
88. What is your favorite kind of car?
89. Do you play poker?
90. What was the coolest concert you have ever been to?
91. Do you have any tattoos?
92. What is your favorite junk food?
93. What's your favorite cereal?
94. If you could change your name, what would you make it?
95. Who's your favorite comic book villain?
96. Do you smoke?
97. Have you ever stolen anything as a child?
98. Boxers or Briefs?
99. Have you ever visited a nude beach?
100. What's your favorite dessert?
101. Have you ever been caught naked by someone?
102. What is your funniest childhood memory?
103. Who is or was your celebrity crush?
104. What is the weirdest dream you have ever had?
105. What are the 3 words that describe you the best?
106. Do you think it’s important to keep up with the news or do you not care?
107. If you had the power to read someone’s mind, whose would it be?
108. Do you like to sleep naked?
109. What are your favorite Christmas traditions that you like to follow?
110. Do you like to sing in the shower?
111. What is your most treasured memory?

Here are some questions you should NOT ask on the first date. The general rule is simple: avoid talking about exes, politics, religion, money, and military – these are so-called “grey areas” which might cause some troubles.

1. If you had a previous relationship, why did your last relationship break up?
2. Have you ever thought of adopting a child?
3. Do you want to have children?
4. Do you have any opinions about politics?
5. Do you still have feelings for an ex?
6. What was your most conflicted emotional moment?
7. What’s been your most intimate experience?
8. Do you believe in any god or gods?
9. Are you afraid of commitment?
10. How much money do you make?

By the way, if we have missed any questions that have worked great for you or you think we could add, hit us a message below in the comments and we'll add any new questions as well!