111 Conversation Starters And Topics To Ignite Killer Dates And Meetings

These conversation starters and topics will spark unique conversations for couples, for friends, or even as a way to get to know someone.

Let’s face it, small talk is boring and often reveals nothing about a person at the onset of getting to know them or spending time with them. If you really want to set a conversation aflame, it’s time to get to the meaningful, meaty, juicy details – with some mindfulness to the context and person’s comfort level, of course. Here are 111 fiery conversation starters that can make a date extra spicy or really any form of meeting a little less bland. These aren’t your typical run-of-the mill questions – in fact, they’re designed to dig deeper and get to the heart of who a person really is.

These are categorized by topics and range from “mild” questions (questions you would pose to someone you don’t know well or aren’t as comfortable with, preferably for platonic meetings or first dates) all the way to red-hot (questions you’d pose when you really want to get personal and your comfort level (or inebriation level) with this person permits it).

Conversation starters about personality and desires


1. Do you prefer going out or staying in during your free time?

2. Do you know your Myers-Briggs type? Does it seem accurate?

3. Would you describe yourself as more of a loner or a social butterfly?

4. What would you spend your ideal night in doing?

5. What does your ideal night out look like?

6. Would you describe yourself as more of an extrovert or introvert?

7. What is one thing people always notice about you?

8. Which hobby do people say you’re obsessed with?

9. Is there a faith or spiritual belief system you identify with most?

10. What’s your most favorite quality about yourself?

11. What’s your least favorite quality about yourself?


12. What’s your favorite guilty pleasure?

13. What’s your biggest pet peeve?

14. What’s the most unpopular opinion or belief you have?

15. If your friends described your worst habit, what would it be?

16. In your opinion, is it more important to be honest or to be kind?

17. What would your loved ones say is your biggest flaw?

18. What would your loved ones say is your biggest strength?

19. Which situations do you find yourself becoming more introverted in?

20. What is one situation that always brings out your extroverted side?

21. What quality turns you off immediately when you first meet a person?

22. What quality makes you most excited when you first meet someone?

23. Who’s your celebrity crush?


24. What is the wildest thing you’ve ever done that you’d love to do again?

25. What is the wildest thing you’ve ever done that you’d prefer never to do again?

26. Is there something on your bucket list you’d never want your friends, family or any future children to know about?

27. What’s the one quality you have you’d never want a future spouse to know about?

28. What one activity do you always do alone that would surprise most people?

29. Are you okay with being rejected? How do you deal with it?

30. What’s the worst consequence you’ve ever faced for doing something you really wanted to do?

Conversation starters for love and dating 


31. What was the most important life lesson a past relationship taught you?

32. What’s the most romantic thing someone has done for you?

33. How would you describe your ideal date?

34. How many long-term relationships have you ever had?

35. Is there anything you always do to ‘prep’ or boost your confidence for a first date?

36. Where have most of your dates taken place – outdoors or indoors?

37. What’s the most memorable way you’ve expressed your feelings for someone?


38. In your opinion, what’s the biggest difference between love and infatuation?

39. What’s your biggest turn-on in a relationship partner?

40. What’s your biggest turn-off in a relationship partner?

41. For you, what physical or emotional trait is nonnegotiable in a partner?

42. What “superficial” quality is a must-have in a dating partner?

43. What “deep” quality is a must-have in a dating partner?

44. What’s the strangest date you’ve ever been on?

45. Do you believe in fate or destiny? Or do you think it’s just a matter of circumstance when people meet?

46. How long was your longest relationship?

47. How short was your shortest relationship?

48. In your opinion, what was the weirdest reason someone has ever broken up with you?

49. If you had to change one thing you did in a past relationship, what would you change?

49. Have you ever been in love?

50. What one quality automatically boosts a dating partner’s attractiveness in your eyes?

51. What’s the most romantic thing you’ve ever done for a boyfriend or girlfriend?


52. Who was your best first-date kiss and why?

53. Which flaw of yours do you try to hide from your partners early on in the relationship?

54. Have you ever had a date that turned into a hook-up?

55. What’s the one thing you’ve done you’d never want a future spouse to know about?

56. Have you ever regretted not hooking up with someone you just met? Who and why?

57. Have you ever wanted someone you couldn’t have? Who and why couldn’t you have them?

58. Have you ever wanted someone you knew you could have, but shouldn’t? Who and why would it have been a bad idea?

59. Which kink of yours do you find most partners do not share? And which do you find most partners have in common with you?

60. Have you ever stayed in a relationship just because of how good the sex was?

61. Do you believe humans are meant to monogamous?

62. Has anyone ever described you as emotionally unavailable?

63. What’s your physical “type” when dating?

64. What’s the worst way you’ve ever broken up with someone?

65. What is the worst date you’ve ever been on?

66. What was the most annoying thing an ex of yours did?

67. Do you believe in the idea that “once a cheater, always a cheater”? Or are people capable of change?

68. How often do you get back together with your exes?

69. What was the worst thing you’ve ever done to an ex that you immediately regretted?

70. What was the worst thing you’ve ever done to an ex that you now feel satisfied about?

71. Have you ever gotten revenge on an ex? How so and how did it feel afterwards?

72. Have you ever cheated on a partner – and do you regret it?

Conversation starters about childhood and upbringing


73. Who inspired you most as a child?

74. What’s your first vivid childhood memory?

75. Do you have a childhood hero?

76. What did you want to be growing up?

77. How many siblings do you have? Are you close with them?

78. Did you have an imaginary friend growing up? What was he/she like?

79. Did you keep to yourself as a kid or did you have a lot of friends growing up?


80. Who do you think treated you better, your mom or your dad?

81. Who did you admire the most in your family?

82. Who did you strive not to be like in your family?

83. Did you belong to any ‘cliques’ in high school? What were they?

84. If your classmates could vote you in for “most likely to…” what designation would they give you?


85. Who’s the one person in your family that causes the most drama?

86. Who do you go to in your family when you need support?

87. What was the scariest thing that happened to you as a child?

88. Do you have a favorite sibling or relative? Be honest.

89. Who is most similar to you in your family?

90. Who are you most different from in your family?

91. Out of all of your family members, who do you wish you were more like, and in what way?

Conversation starters about dreams and careers 


92. How would you describe your current job title?

93. Is your current career the same as your true passion?

94. Do you think the job you have right now is the one you want long-term?

95. What are the best things about the job you have now?

96. What are the worst things about the job you have now?

97. Where do you want to be a year from now?

98. Do you like getting things done right away or checking off a to-do list gradually?


99. What’s the best thing you’ve ever manifested in your life?

100. What’s the worst thing you’ve ever manifested in your life?

101. If you had all the money in the world to do what you really wanted, how would you spend your time?

102. What is one goal you feel like you’re sabotaging yourself in?

103. What’s one goal you really want to achieve but keep finding excuses not to?

104. What’s one goal you’re ridiculously proud of accomplishing and want everyone to know about?


105. Have you ever lied in a job interview? What was the lie?

106. What’s the biggest way your professional persona differs from your true self?

107. What’s one quality you bring to a job you wish more people would notice?

108. What’s one way your colleagues underestimate you?

109. What secret do you have that your co-workers would have a hard time believing is true?

110. Do you enjoy careers that challenge you to grow or careers that give you a sense of peace and purpose?

111. What’s one unique quality that makes you stand out from others who also do what you do? Thought Catalog Logo Mark

Shahida is a graduate of Harvard University and Columbia University. She is a published researcher and author of Power: Surviving and Thriving After Narcissistic Abuse and the poetry book She Who Destroys the Light.