No points for guessing, but dating can be a serious affair – especially if it’s your first date. Getting into ‘chatting mode’ with a person you don’t know much can be awkward. And a first date is no casual interaction. It’s almost a personal interview that helps the other decide how interesting, intriguing, and attractive your personality is.
Therefore, you just cannot afford to not get your act together.
Many first-timers have trouble striking a conversation during a date, and some usually end up taking the cliched route. If you’d like to come across unique and make the experience a fun and memorable affair for both, I suggest sprinkling in some more creativity and lateral thinking.
The following are the best questions to ask on a first date:
You just don’t start a conversation focused on the other person. Any conversation – be it a date or a business meeting – should begin with an emphasis on the surroundings. Therefore, begin the conversation with any or all of these questions.
• What do you think about this place?
• Have you been here before?
• Do you come to this place often?
After having greeted each other, or having asked questions such as “how was the day?“, the following questions should help you maintain the flow.
1. Where are you from originally?
2. Where do you live currently?
3. Which school/college did you go to?
4. What subject did you major in?
5. Where do you work?
6. When is your birthday? And guess her zodiac sign after getting the response.
These questions will help you learn the background of the person, and also how attached or detached she is to family.
7. What do your parents do?
8. Do you have siblings?
9. Are you living with your parents? If no, where are they based and what are they doing?
10. What was growing up like? How were your childhood days? Were you a naughty kid?
11. What is your most striking childhood memory?
12. Who are you the closest to in your family?
13. Who are you closest to? Mom or dad?
14. Do you have a lot of friends? How are they like?
15. Who’s your best friend? What makes him/her so special to you?
16. What’s the single most stringently followed tradition in your family?
Learning the Personality
This is probably the phase where you’ll either talk a lot or hear out the person more. These questions will help you get to know the individual more, without getting too personal.
17. What do you hate the most about dating, or having an extended conversation with a stranger?
18. What was going through your mind before this date? Were you mentally prepared or nervous?
19. What does your name mean? (Ask this question only if the name’s unique or representative of another language/culture)
20. What’s one secret skill you are yet to make use of?
21. What do you do when not at work?
22. What, according to you, is essential for a good conversation/time?
23. Are you an introvert, or you love to hang out with people more?
24. Do you like watching movies, or do you prefer TV more?
25. What kind of music do you like?
26. When you were a kid, what did you wanted to grow up as?
27. What’s the best present you ever received, or gifted?
28. Are you an avid traveler? If the answer is in the affirmative, ask interesting places she has been to in recent years. (Talking about travel can open up a can of related topics or questions)
29. If the traveling part clicked, learn more about the vacations the individual has been to in the recent past. For instance, you could even ask the kind of vacations she prefers. Or, what is your dream or favorite travel destination?
30. Do you like reading books? If yes, then ask the recent book she read or her favorite books.
31. What is your favorite cuisine and/or restaurant?
32. Do you like sports? Which is your favorite team?
33. What’s your biggest fear?
34. Are you scared of aging?
35. What irritates you the most?
36. Do you like cats or dogs?
37. What is that you love the most about your city/town?
38. What turns you off the most in the opposite gender?
39. Are you a coffee or tea person? Do you like your beverage in the shop, or prefer making them yourself? How long did it take to realize your love for the beverage?
40. Do you like wearing formals, or are you a ‘casuals’ person?
41. Do you like early mornings or are you a night owl?
42. Do you like gaming/technology? What’s your take on smartphones? Do you think Apple products are overpriced?
43. Do you cook your own food? If yes, what are your signature dishes? If no, have you ever even thought of giving cooking a shot?
44. How social are you? Do you believe in meeting people in person or are you more into social media?
45. What kind of movies do you like? Rom-coms, horror, romance, etc.?
46. What’s your favorite movie? What do you think about the Godfather?
47. What is that one thing you’ll consider yourself extremely bad at?
48. What is the one thing that has made you feel extremely proud about yourself?
49. Is there any sport or activity you’ll love to take a shot at?
50. Do you really like dating? How comfortable or uncomfortable are you with the concept?
51. If you like music, ask the other person about her love for music? If there’s interest, ask the individual about the recent concerts she has been to.
52. Do you listen to your brain or go by intuition?
53. Everything’s fair in love and war! Do you believe in the phrase, or have contrary thoughts?
54. Would you mind if I take a bite of your food? (This may sound intrusive for a first date, but it’ll certainly reveal how open or sharing the other person is)
55. Do you smoke or do drugs?
56. Is there any food item you completely despise?
57. What are you the most passionate about? And what drives that passion?
58. Do you watch Game of Thrones? Do you feel it’s overrated?
59. Do you make/stick to schedules or are you the spontaneous kind?
60. During distress or tough times, who’s that one person you talk to or count on the most?
61. Who was your first crush and when did that happen?
62. Do you believe in New Year resolutions?
63. Do you believe in saving for the future? If yes, what are you currently saving up money for?
64. What makes you happy the most, other than family and friends?
65. Do you celebrate birthdays? Which one is your best yet?
66. What’s one brave thing you’ve done that you’d probably won’t repeat?
67. What is the luckiest thing ever happened in your life?
68. Did you ever have near-death encounters?
69. What’s the one simple thing you’re hopeless at?
70. What’s the most surprising aspect about your personality?
71. What is the most random thing you have ever done?
72. Do you like desserts or salty snacks?
73. Who is your favorite college professor or school teacher? And why?
74. How was school or college life? Were you a popular student?
75. Any crushes during your learning days?
76. If you look back at school, what would you consider the most embarrassing experience?
77. What subject/activity did you excel at in school?
Fun/ Hypothetical Questions
If you’ve reached this stage, it means you are now enjoying each other’s company or have gotten a bit more comfortable with each other. These are kind of personal questions, which don’t reveal the intimate side of the individual. This would perhaps be the funniest phase of your meeting.
78. What is the one food you can survive on for the rest of your life?
79. Do people call you by nicknames? How did those names come about?
80. Who is your biggest celebrity crush?
81. If you could take rebirth as another person, who would you like to be? And, why?
82. If given an option, which country or city you’d like to settle down in? And, why?
83. Do you think the Kardashians suck? Or you have another opinion?
84. If your apartment or house catches fire, what are the things you’d save first?
85. Are you on Tinder? Which is the weirdest pickup line ever used on you?
86. If you had to jump in a pool, what would you like the pool to be filled with? Chocolate, cream, water, or anything else?
87. If you become the king of the world, what’s the one thing you’ll change right after taking charge?
88. Which body part of yours is the most sensitive/ticklish?
89. What is that one job you would/could never do even it paid a fortune?
90. How many pair of jeans do you have?
91. Can you recollect what’s in your fridge at the moment?
92. Do you think aliens exist?
93. Tell me five personalities you think would never make it to heaven.
Thoughts align with not just emotional connect, but also when you realize you have similar ambitions. These questions should help you understand what you’re looking for in relationships and also life, in general.
94. Do you have a bucket list? If yes, how far have you come through?
95. Are you career-driven?
96. Does your current job/profession excite you? If no, what’s your field of interest, or are you considering entrepreneurship?
97. Who’s had the maximum influence on your career or your life?
98. Do you like your boss?
99. What is the best piece of advice you’ve ever received?
100. Who’s that one individual you admire the most?
These are the ending moments that aren’t decisive by themselves. By this time, you’ve already created an impression (good or bad). But if you fumble here, you could still spoil your chances of getting another date with the person.
101. How was the food?
102. Did you enjoy the place?
103. What are your feelings about this date now? Do they match or contradict your pre-date notions?
104. What’s your plan for the next weekend?
105. How will you get back home? Shall I drop you at your place?
106. Is there anything I should know but I never thought asking?
Ask the following questions if you’re confident of having managed to win over the person through your charm.
107. There’s this bar I know on the next street? Would you like to have a drink?
108. Would you like to have some dessert somewhere else?
109. My friend lives some blocks away. There’s a party happening there. I’ll be heading there next. Would you like to give me company?
110. I had a wonderful time, and I hope you did too. When are we meeting again?
The aforementioned questions not just help you know more about the other person, but they’re also conversation-builders, and don’t make you sound lame.
Kindly stay away from personal or sensitive questions. If you people end up liking each other’s company, you’ll always have opportunities to get in deeper with your friendly interrogation. And if there’s just no chemistry or if you aren’t keen on meeting the person again, then getting to know the other individual personally is plain irrelevant.
P.S. The dating questions to ask need not be in a particular order. These are options. Pick one that’s suit your personality, preference, and of course the date and the actual ambiance. And even if you have prepared a list, mix things up based on the responses. Your questions must lend to the natural flow of the conversation. Avoid turning this first date into an interview!