100 Best Questions To Ask On A First Date

Are you going on a first date and nervous about keeping up a good conversation? Here are 100 great questions to ask to keep the conversation flowing!

By E.M. Love
100 Best Questions To Ask On A First Date

First Date Conversations

First dates can be very stressful to get ready for. If you don't know the person you are going on a first date with, you may be feeling extra anxious. You may be afraid of the conversation dying out and having nothing to talk about, leading to you and your date just sitting there in awkward silence. Deciding some conversation topics before you go out on your date can help avoid not having anything to talk about and avoid those awkward moments of silence when neither of you are sure of what to say. The easiest way to keep conversation easily flowing is to ask all kinds of questions, from funny to serious. Feel out the person and ask appropriate questions that they will feel comfortable answering, otherwise you may cause unnecessary tension during your date. Doing this can help you learn more about your date than you otherwise would, helping you decide faster if a second date with that person is worth it.

First Date Conversation Questions: For the First Few Minutes

When you first sit down for your date, you guys are still not very comfortable with each other so it is best to ask simple questions that anyone is fine answering. This will help start your conversation off right while avoiding any drama that may upset the rest of your date night. Below are some great questions to ask when you are first starting your date. 1. What college did you graduate from? 2. What did you major in? 3. Where are you from? 4. What do you do for a living? 5. How did you decide to do that for a living? 6. Where do you live? 7. What do you enjoy about living there?

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First Date Conversation Questions: Over Drinks

When drinks come to the table you should have asked the most basic questions already, so you guys are starting to have a feel for each other now. You can start to ask more specific questions to learn what your date likes and dislikes, and try to find similar interests. Learn about what they like to do for fun and places they enjoy going to. Here are some great questions to help you learn more about what your date likes to do: 8. What do you enjoy doing in your spare time? 9. Would you rather watch TV or a movie? 10. What is your favorite TV show/movie? 11. What is your favorite type of music? 12. Who is your favorite artist? 13. Do you like to travel? Where have you been? 14. Do you have any upcoming travel plans? 15. Do you like to read? Have you recently read any books that you really enjoyed? 16. What is your favorite book that you have ever read? 17. What are your favorite toppings for a pizza? 18. What would make up the perfect burrito for you? 19. Do you drink alcohol? How often? 20. What is your favorite drink? 21. Do you like salty or sweet better?

First Date Conversation Questions: When You're Comfortable

Now you guys should be feeling a lot more comfortable with each other from asking and talking about the above questions. You and your date probably have found a few common interests so you are both feeling a little more relaxed. Now is a good time to start asking some deeper questions that are fun, funny, and serious, but can teach you a lot about your date and their true nature. 22. Do you prefer cats or dogs? 23. What one food would you want to eat for the rest of your life if you could eat nothing else? 24. Do you have any older or younger siblings? 25. Do you have any nicknames that your friends call you, or any childhood nicknames? 26. If you won the lottery, what would you buy? 27. If you could be someone else, who would you be and why? What would you want to do as that person? 28. Do you prefer to drink coffee or tea? 29. If you could live anywhere, where would it be? Why? 30. What bothers you the most? 31. Where did you live as a kid? 32. Where do your parents live? Do they still live in the same house that you were in as a kid? 33. What do your parents do for work? 34. Do you have a bucket list? What is on it? 35. Do you prefer mornings or nights? 36. Do you like cooking? What do you like to cook? 37. What foods do you hate and can't stand to eat? 38. Do you enjoy your job? What do you like about it? 39. What is the part that you enjoy the least about your job? 40. If you could change jobs, what would you want to do? 41. Have you ever had a really bad job? What is the worst one that you have had? 42. Are you really social? What do you and your friends do? 43. Do you have a lot of close friends? How many friends are you really close to? How many friends do you have that are more of acquaintances? 44. Are you focused on your career? 45. What is your biggest passion? 46. When is your birthday? What sign are you? 47. Who has influenced your life the most? 48. What is your favorite spot in the whole world? Why? 49. What is something that makes you laugh the most? 50. What is your main goal in life as of right now? 51. What is your favorite thing to do on weekends? 52. What is your family like? Did you like growing up with them? 53. What do you think of yourself when you were a kid? 54. What do you think I should know about you? 55. What is the best gift you have ever gotten from someone? 56. What is the worst gift that you have ever gotten? 57. What have you accomplished that you are very proud of? 58. What is something that you want to try out? 59. What is your favorite thing about dating? 60. What do you hate the most about dating? 61. What are you bad at doing? 62. Who is the closest family member you have? 63. Which holiday do you enjoy the most? 64. What is one of your favorite memories from childhood? 65. What is your favorite clothing article that you like to wear? 66. Are you saving for anything special right now? 67. Do you have a New Years resolution that you are following through on? 68. What is a type of job that you would be completely against ever taking on? 69. Do you have a dream job that you would start in a heartbeat? 70. Do you like to plan or would you rather do something last minute? 71. What is something spontaneous that you have recently done? 72. Do you like sports? 73. What is your favorite sport? 74. Do you play any sports? 75. Do you have a favorite sports team? 76. What qualities do you not want in someone that you are in a relationship with? 77. What qualities do you definitely want in someone that you are in a relationship with? 78. What would your closest friends say about you? 79. What is the best advice you have ever gotten from anyone? 80. If you could time travel, when would you travel to and why? 81. What do you wish that you knew when you were a teenager? 82. What is your favorite family tradition that you had while growing up? 83. When you were growing up, what did you want to be? 84. What do you wish you could do better? 85. What is your favorite charity and why? 86. How would you tell people about yourself? 87. What do you think is the most attractive trait in someone else? 88. What is your favorite animal? 89. Who would you want to be stuck on an island with? 90. What is your dream house? 91. What is your idea of a perfect day? 92. What are you most grateful for in your life?

First Date Conversation Questions: Deciding on a Second Date

Now that you are getting close to wrapping up your date, you can ask some deeper questions that may be more touchy but will help you decide on if you want to go on that second date. These questions will also help you pave the way to getting that second date if that is what you want. 93. Can we split the check? Can I leave the tip? 94. Are you going to be really busy with work this week? 95. What do you think of this place? Did you enjoy it? 96. What are your weekend plans? Are you doing anything fun? 97. Is your next week going to be really busy?

First Date Conversation Questions: Keep Date Going

If you guys are really hitting it off and you don't want the date to end, ask some of these questions to show that you want to spend more time with them right now. 98. Do you want to go get a drink? I know a great bar nearby. 99. Do you want to go get some coffee and dessert? 100. My friend is having a party nearby, do you want to go?

Conclusion: First Date Conversation Starters

First dates can be very scary but if you are prepared you will feel much more confident. These questions will help give you conversation topics, from funny to serious, to avoid any of those awkward silent moments during your date. This gives you ideas for questions that are funny and will have you both laughing at the answers that you guys give, helping you guys connect on an emotional level. There are serious questions that will help you understand your date better. You will learn about their childhood and family, which helps explain the kind the person that they are today. You will see if they are close to their family and the kind of relationship they have with them, which may be a tell-tale sign of how they would be in a relationship if you decide to pursue one with them. They will tell you about their goals in life, their likes and dislikes, what they are good at, what they are bad at, among other things that make them up as a person. Here are also some great questions to help you continue a good date into the night, and to lead your date into agreeing to go on a second date with you if that is what you want.