Have you ever met a person but wished you got to know them better? Or maybe you are looking for ways to turn chitchat into a real conversation. Either way, this short post gives you 15 questions or conversation boosters that can spice up a chat at any time!

First, you will read five what-if questions that are ideal to use with people you have just met. They can be the starting point for great discussions, while you also get to know them better.

Next are five what-question that aim to dive deeper into one’s personality and traits. If you feel comfortable with the other person, feel free to use them. Note, though, that they are more personal than the first five.

Finally, the last five questions are deeply personal, and you may use them with people you know well, but you still want to discover more about them. They are also ideal for bringing a discussion back to more serious talk instead of chitchat.

Five if-questions to make any conversation fun

  • If you didn’t have to sleep, what would you do with the extra time?
  • If you could turn any activity into an Olympic sport, what would you have a good chance at winning medal for?
  • If you could have a video of any one event in your life, what event would you choose?
  • If you could make one rule that everyone had to follow, what rule would you make?
  • If you could make a 20-second phone call to yourself at any point in your life, past or future, when would you call, and what would you say?

Five what-questions to move from chitchat to a conversation 

  • What game, book or movie universe would you most like to live in?
  • What could you give a 40-minute presentation on with absolutely no preparation?
  • What are three interesting facts about you?
  • When people look at you, what do you think they see/think?
  • What have you created that you are most proud of?

Five personal questions for the ultimate conversation boosters

  • What lifestyle change have you been meaning to make for a while now?
  • What do people think is weird about you?
  • What’s the most illegal thing you’ve done?
  • What would be some of the most annoying things about having yourself as a roommate?
  • What do you most often look down on people for? What do you think other people look down on you for?


  • Whenever you see a conversation derailing into superficial chitchat and want to spice things up, use any of these questions. 
  • And don’t forget to follow up with more questions about what the other person mentions. 
  • There is no need to start asking the above questions one after another. After all, this is a discussion, not an interview.

Write A Comment