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100 Different Questions to Ask When Dating: Both Online and Offline

100 Different Questions to Ask When Dating: Both Online and Offline

Questions to Ask When Dating

So lockdown has got us relying on… wait for it… ACTUAL CONVERSATION! Uh huh. It’s picking out the guys with ‘all looks, but no substance’ and is actually proving pretty eye-opening. It does mean however, that conversation has actually never been so important. So here’s 100 different questions to ask when dating, to help you get to know a person a little bit better.

This is once the standard questions about work, family, hobbies, etc are out the way and you want to spice up the chat a little bit. Now I wouldn’t ask them all at once, clearly… that would be weird!! This isn’t an interview, after all. But, these will certainly give you a lot of insights into what this person is all about.

Throw the odd question into a conversation here and there, use them as part of a virtual date night (with lots of quick fire questions!), or turn it into a game if you’ve started to get to know the other person better now… Try to guess their answers and use a points system to add a bit of competition. It will certainly be interesting to see who’s been listening to the other person more!

So without further ado, here’s 100 questions to ask when dating. Have fun!

100 Different Questions To Ask When Dating

  1. What’s the one thing you love the most about yourself?
  2. If you could change one thing about yourself, what would you change?
  3. What do you think people are more attracted to – your looks or personality?
  4. And what do you think are the most attractive qualities in a partner?
  5. What attracts you the most to someone physically?
  6. Are you in touch with your emotions? Or do you find it difficult to say how you feel?
  7. How about when it comes to how others are feeling? Are you in touch with this? An emotional empath? Or often miss the signs?
  8. Do you get affected by the things people say or the way people act towards you?
  9. What do you think is the one thing that makes you a great partner?
  10. Complete honesty – what area of relationships do you think you could improve on?
  11. What do you think is the best thing about being in a relationship?
  12. On the flip side, what’s the best thing about being single?
  13. Tell me your most hilarious dating story!
  14. How about your idea of the perfect first date?
  15. What do you think shows the kind of person someone really is?
  16. How long do you think it truly takes to get to know someone?
  17. What’s your biggest fear?
  18. And what excites you the most in life?
  19. What’s your greatest achievement?
  20. Do you have any regrets? If so, what are they and do they play on your mind still today/
  21. What are five things on your bucket-list?
  22. How do you think you’re different now, to say, 5 years ago / 10 years ago / when you were in school / college / uni? etc.
  23. What’s one thing that not many people know about you?
  24. Do you think most people show their true self?
  25. Are you growing up to be the person you really want to be?
  26. If you could throw one crazy ‘plot twist’ into your life, what would you do?
  27. Where do you see yourself being in five years time?
  28. What did you used to want to do when you were growing up?
  29. How about your parents – what do they do?
  30. Who do you think you’re most similar to, your Mum or your Dad?
  31. If you could have (another) brother or sister, what would you have, and how old would they be?
  32. How do you think your childhood and upbringing has influenced the person you are today?
  33. If you could be better at anything, what would it be?
  34. What’s the biggest life lesson you’ve learnt so far?
  35. Are there any wrong assumptions you think people make about you?
  36. If yes, what do you think gives them that impression? And is it a bad thing?
  37. Do you think you’re an over thinker? Or don’t think things through enough?
  38. Would you say you’re an introvert or extrovert?
  39. What are you the ‘go to guy for’ amongst your friends?
  40. Tell me about your best friend and the type of friendship you guys have!
  41. Do you think you typically follow the crowd or make your own path?
  42. When have there been times where you’ve gone against the norm? Or, what’s been the most spontaneous, out-there thing you’ve ever done?
  43. What’s one thing that holds you back?
  44. And the one thing that drives you the most?
  45. Who is your biggest inspiration and why?
  46. What do you think is the most important thing in life?
  47. Do you have any morals or beliefs you choose to live your life by?
  48. What’s the worst advice someone has given you?
  49. How about the best advice someone has given you?
  50. Based on past experiences, what’s been the best year of your life so far and why?
  51. If you could go back to any year in your life and re-do it, would you choose to go back and which year would you go to? Again, why?
  52. Would you like to be famous? And if yes, what for?
  53. Have you met many famous people? If so, who and where?
  54. Who do you think is your celebrity lookalike? 
  55. If you could be an animal, what animal would you be and why?
  56. What do you prefer – sweets or chocolate? Fruit or veg? Burger or pizza? etc.
  57. Are you comfortable in your own company? Or do you prefer being around people?
  58. What nicknames have you had over the years and how did you get them?
  59. If you were to do a pub quiz on one specialist topic, which would you be best at?
  60. What are your top three favourite things to talk about?
  61. And how about your least favourite things to talk about? What BORES you?!
  62. Do you have a weird obsession? (Come on, be honest!)
  63. If you could travel anywhere next, where would you go?
  64. How many different countries have you currently visited?
  65. What have been your best and worst travel experiences?
  66. If you could live anywhere in the world (and take your friends + family) where would you live? And why?
  67. What’s the most complex meal you can cook?
  68. If you could eat one type of food for the rest of your life, what would it be? (Italian, Thai, etc)
  69. What are three foods you would love to try?
  70. Tell me your go-to drink on a night out!
  71. What’s your dancing style like on a night out?
  72. Which would be more you: netflix or nightclub? And why?
  73. Are you more an indoors or outdoors person?
  74. How often do you exercise / work out?
  75. Do adrenaline activities entice you or scare you?
  76. What is one thing you would never do? For any amount of money!
  77. How long do you think you could go without having any access to the internet or your mobile phone?
  78. Are you more of a tidy or messy person? Have a good or bad memory? Are a morning person or night owl? Etc. Play around with different comparison options.
  79. Would you rather go rock climbing or white water rafting? Skiing or surfing? Cycling or running? Etc. Again, play around with different options. There could be so many!
  80. What would be your ideal way to spend the day?
  81. How about the best way to spend a night?
  82. If you could listen to just one music artist for the rest of your life, who would it be and why?
  83. What’s the last book you read? The last documentary you wanted? The last movie? Etc.
  84. If you could solve one problem in the world, what would it be?
  85. What mantra do you try to live your life by? Or what are some of your favourite life quotes?
  86. Are you a glass half full or half empty kind of person?
  87. What little quirks do you have, or have been told you have?
  88. Are you a people watcher? If so, are there any memorable or funny people watching moments that spring to mind?
  89. What’s one thing you’re really looking forward to?
  90. How about one thing that takes up far too much of your time?
  91. Who is the most knowledgeable person you know?
  92. What mystery do you wish you knew the answer to?
  93. Are you superstitious? 
  94. Do you believe in star signs and astrology?
  95. Are there any conspiracy theories you swear are true?
  96. What fad or trend would you love to see make a come-back?
  97. If you could have a superpower, what would it be and why?
  98. What’s the ‘luckiest’ thing that has ever happened to you?
  99. Which small things mean the most to you?
  100. What are we going to do when we can finally see each other?!

So there we have it – 100 different questions to ask when dating. You can use these online, over the phone and eventually on real-life dates… they’ll feel like a treat when we get them, hey?! In the meantime, try to make the best of a bad situation. Remember, this won’t last forever.

Stay safe and well.

See Also
How To Become Comfortable With Uncertainty

Love,
Ell_xx

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Different Questions to Ask When Dating

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View Comments (2)
  • Wow there are some interesting questions that I would never have thoughot about. I am certainly grateful and shall save the link for future reference.

    Thank you, Ella!

  • I find these questions really informative, its going to help me keep the conversation going for a long time with my partner. I will use one question at a time to begin a conversation that will take while.

    Thanks for making the list

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