83 Good Questions To Ask On a First Date To Deepen Your Connection



Couples talking

Most guys and girls agree on having a difficult time figuring out things to talk about on their first date.

It’s true that when you meet someone for the first time you are quite clueless about what’s the right or wrong thing to ask them. Groping for things to talk about, while on a date, can leave you feeling awkward and discomfited.

This is why is best to be prepared with a list of questions you intend to ask your date during your first meeting – this will serve two purposes.

  1. You can pop in a question every time there is an space of silence in your conversation and thus avoid awkward silent moments.
  2. You can find out a lot about your date using these questions which in turn open up new avenues of conversation.

First dates can almost be thought of as the first round of interview before the candidate is selected for the second date. Girls are generally more probing and curious during the first date while the guys tend to be a lot more reserved in their questions.

Good first date questions are the ones that help you understand your date better in terms of their mental and emotional make up. There are three levels of questions that you can ask depending on how your date is coming along, they are as follows.

a. Ice breaker questions – These are some good conversation starters questions to ask on a first date to get some rapport going.

b. Surface level questions – A little more probing than ice breaker questions but not too personal. These date questions should reveal certain interesting traits in your date.

c. Deep level questions – These type of first date questions will be personal and judge how comfortable your date is about sharing some intimate information with you.

Let’s have a look at the questions that fit into these three categories.

A. Ice breaker questions

If you end up dating someone who is quite contend maintaining silence, you will need to initiate some ice breaker questions if you want to get some talk flowing.

Some good conversation starter questions for the first date are as below:


1. Where were you born?

2. Where did you do your schooling or graduation?

3. How do you relax or unwind during weekends and working days?

4. What’s your favorite drink?

5. What’s your favorite hang out place and who do you usually hang out with?

6. How’s your work or college life coming along?

7. What kinda sports are you interested in?

8. What do you like about this city?

9. Are you a foodie?

10. What do you do for fun at home?

11. Do you have any specific hobby going?

B. Surface level questions

Depending on how you are getting along you might feel the need to ask some probing questions to your date either out of curiosity or genuine interest.

Some good surface level questions to ask here are as follows:

12. Who was your favorite teacher at school?

13. What makes you laugh?

14. What was your favorite toy when you were a child?

15. Do you feel comfortable in a crowd or do you prefer your personal space (in other words, are you an extrovert or an introvert?)

16. Do you work out? (avoid this question if your date is a little on the plump side)

17. Tell me about your present friend circle.

18. What were you like as a kid?

19. Are you involved in any specific hobby or venture beyond your work.

20. Are you religious? (be prepared to be surprised).

21. What kinda job are you into and how do you find your work?

22. How do you spend your weekends?

23. Do you like to travel, if so what are the places you have traveled to?

24. What’s the one thing you hate about yourself?

25. If money were not a concern, what will be your dream job?

26. Are you an early bird or a night owl? (or, are you a morning person or a night person?)

27. What is your favorite place to travel to?

28. What is the most interesting place(s) you have traveled to?

29. What was your favorite place to travel to when you were a kid?

30. What was your favorite childhood memory?

31. What is your favorite thing to do when you travel?

32. What is your favorite restaurant?

33. Have your tried any unique cuisine? If so, which one and how did you like it?

34. Is there any food that you dislike eating?

35. Do you enjoy cooking? What is your favorite thing to make?

36. What kind of music do you enjoy listening to?

37. Who is your favorite music artist?

38. What is your guilty pleasure?

39. Do you have pets? Have you had pets growing up?

40. What is your favorite kind of pet?

41. What is your favorite T.V show of all time?

42. What is your favorite sitcom?

43. What is your favorite thing to do outdoors (or indoors)?

44. What does your usual day look like for you?

45. Do you like reading?

46. What’s the last book you read?

47. What are your pet peeves?

48. What is your most favorite beverage?

49. What’s the worst job you ever had?

50. What is your start sign?

51. Do you have any odd talents?

52. Do you play any musical instruments?

53. What is your favorite cuisine?

Any question that is on the personal level but not too much on the emotional plane would qualify as a surface level question.

If you find your date responding to these questions in an open manner it will indicate that he/she is quite comfortable in your company.

C. Deep level questions

If you are really getting along well and you find yourself getting curious to know him better, then you might want to pop in a few deep level questions that touch the emotional front.

But remember that some of these questions will probe your date on the emotional front and he/she might find it a little too personal if they are not very comfortable talking to you. It is important that you have some level of rapport going before you ask these questions.

Some good deep level questions to ask are as follows:

54. What is your definition of happiness?

55. Which possession that you have now do you think you will still have in 30 years time?

56. What is the one thing that some-one you loved could do to you that you would find unforgivable?

57. What is that one thing you would like to change about your life right now?

58. Who’s the person you are closest to presently?

59. What are the things that you hate about yourself?

60. How’s your relationship with your father and mother? ( this can get a little too emotional in some cases)

61. Tell me something about your childhood.

62. Is there anything you are stressed out about in your life right now?

63. What’s been the toughest phase in your life till date? (a little too personal)

64. What are your plans for the life ahead?

65. Do you believe in God?

66. What are your thoughts on social media?

67. Do you have a favorite quote, saying or motto? If so, what is it?

68. What are your thoughts on veganism?

69. What do you make of the current political scenario?

70. Who/What inspires you the most?

71. What would your perfect vacation look like?

72. Do you believe in climate change?

73. What are your thoughts on sustainable living?

74. Do you enjoy art? If yes, what kind of art do you enjoy?

75. What’s the best advice anyone ever gave you?

76. Have you ever wanted to start your own business?

77. If you could live anywhere, where would you live?

78. If you could switch places with anyone in the world who would it be and why?

79. What about you makes you proud to be you?

80. How is your relationship with your family?

81. Do you believe there is life on other planets?

82. How has life been treating you this far?

83. What is the most important lesson you have learned in life so far?

You will get better answers to your deep level questions if there is a good rapport going on between the two of you or else the answers will be guarded.

If you are not genuinely interested it will show. As they can be a little sensitive make sure you earn some level of trust before you venture into the territory of deep level questions.

Some standard things to talk about

Couple on a date

The following are a few standard things to talk about on your first date that will keep your conversation fun and interesting. If you have a tough time memorizing the questions, just keep these points in mind and you should be good to go.

1. What’s your date wearing?

There are several personality traits hidden in the way a person dresses. Some people dress snappy while some are uber casual. Talk to your date what he or she is wearing by either complementing it or commenting about it. Don’t say anything critical though.

2. If you have interesting hobbies, talk about it

What do you do during your idle hours? This is a safe line of inquiry that opens up new avenues of subjects to talk about. You can tell your date about your hobbies and see if you can get him/her interested.

3. Talk about childhood

Which school did you go to? Where did you live as a kid? These questions make for good stuff to talk about on a date. Everyone loves to talk about their childhood and there are bound to be some interesting stories to share.

4. Do you have pets?

People who have pets love to talk about them. So if your date has a pet at home, it makes for a good subject to discuss on and if you both have the same type of pet, well you have a chemistry going already. You can also talk about the pets you friends or family members have.

5. Relatives and family can make for good subjects

Guys usually shy away from talking about their relatives and family while girls are quite keen on talking about them. There is usually something interesting to talk about a grandpa or a grandma or that bratty cousin and you can always talk about the eccentricities of your uncle or father.

6. Food is a favorite topic

Most people are foodies to a small or large extent so food becomes a great subject to talk about on a date. Discuss about what you like rather than what you dislike, ask your date about the various cuisines he/she is interested in or any unique ones that they’ve tried. You can also talk about the cocktails you like and your cooking skills (or lack of it!).

7. Places you have been to

Don’t we all love to listen about places we’ve never been to? Ask your date about where he or she did her education or the places they’ve traveled to. If you’ve been to some interesting place or traveled to some distant country, talk about their attractions and culture. You can also talk to your date about the places he/she would like to visit.

8. What have you been listening, reading and watching?

Favorite sitcoms, movies, music, actors, icons or anything else related to the arena of entertainment can bring out a lot of topics to talk about on a date. If you share a common interest in a genre of books or music, it becomes a good topic to discuss about. Celebrity gossip can also make for interesting stuff to talk about on a date, just make sure your date is equally interested.

Our list of top 7 questions

The following is our pick of the top 7 questions to ask.

1.) What makes you laugh?

The chances are that if you have been with some-one for a while you may already know the answer to this question but still some answers may surprise you. In a new relationship it is a real eye-opener and can tell you a great deal about this new person in your life.

What makes us laugh is an essential part of who we are. It says a lot about our values and our outlook on life. The answers are just as interesting if you ask yourself the same question.

2.) What was your favorite toy when you were a child?

This fun boyfriend question often opens the flood gates on memory and you may have a problem getting the person to stop talking! This question serves three purposes. It will tell you something about your boyfriend’s personality. It will also tell you a great deal about his childhood, as relating stories of this kind will mean discussing the wider subject of being young. Thirdly it will give you an insight into emotions and reactions. When some-one reverts to childhood memories they often subconsciously revert to being parts of the child they were. Children hide less or do it less effectively. Listening to some-one recall in this way can often feel like you are looking in through a very clear window. This is a great question to understand your boyfriend better.

3.) What is your definition of happiness?

Equally ‘happiness’ can be substituted with love, friendship, wealth, loyalty etc. These can be either incredibly easy or incredibly difficult questions to answer but the point of all these questions is to get talking and discussing and gaining some insight. Answers themselves are not always the most telling things. Sometimes the way in which some-one answers can be very revealing. This is a great question to ask to get to better know someone.

4.) Which possession that you have now do you think you will still have in 30 years time?

This fun question strips away any obvious answers like an X-box, a car or his beloved new cell phone and gets to the real essence of what he values and loves.

5.) What is the one thing that some-one you loved could do to you that you would find unforgivable?

You would think the obvious answers would be things such as be unfaithful, steal from me, violence etc but I have asked this question of many people and have been fascinated by the answers. The initial answer is often one of those listed above but is often added to in quite surprising ways. Try it and see.

6.) Who was your favorite teacher at school?

This question will reveal in the same way as the ‘what was your favorite childhood toy’ question. You can also ask you boyfriend what his favorite subject was and why. This is another great question to get to know your boyfriend better.

7.) What is the most important lesson you have learned in life so far?

This a great question for determining the levels of cynicism or optimism of the person you are questioning. It is one of those fun questions that can be very revealing and may lead to deeper insights than you imagined.

Points to bear in mind before asking these questions

Here are a few points to bear in mind while you go about asking these questions to your date.

  • All the questions mentioned in this article are good for the first date, but just make sure your timing is proper. Asking too many questions at once can put your date on the defensive or just make him/her panic.
  • Most people are not very comfortable answering questions if they feel they are being probed, so just pop the questions in very casually along the flow of the conversation.
  • Don’t pop in multiple questions one after the other, it’s okay to have a little silent space so that she can ask you some questions of her own.
  • Avoid asking questions like what’s your favorite movie, color, music and stuff like that, because it sounds too interview like. These details are not important on your first date.
  • You don’t want to come across as someone who has prepared a list of questions in their rote memory. Just pop in the questions as casually as possible and be genuinely interested in her answers, you can find new questions to ask based on her answers – this way there will be a natural flow to your conversation.
  • Maintain a non-judgmental and relaxed attitude and just be interested in sharing and listening. This simple mantra can help you feel relaxed and enjoy your date.
  • One secret to success here is to make it a reciprocal exercise. You have to take your turn too. If you are not prepared to reveal things about yourself then you can hardly expect some-one else to.

In conclusion

In conclusion, just be relaxed and try to listen more than you try to talk. Listening by itself will help you come up with new subjects to talk about. On a date, it is important to come across as someone who is as interested in listening as in sharing.

And remember, if you run out of things to talk about on a date, you always have the weather to comment on.