50 Questions You Can Ask While Video Chatting to Start a Conversation

Ever have an awkward start to a video call with a friend or co-worker? Or find you’re only talking about how stressful things are? Check out these 50 open-ended questions to get a more cheerful conversation going

Like many others, I have been FaceTiming friends more often to keep in touch. After a conversation with a pal in London, in which we spiraled out about everything from going to the grocery store to our parents' health, she texted me a list: "Conversation Starters" and added, "feel free to add to the list for next time we chat."

Excusez-moi? Do anything but constantly talk about how scary everything feels? The idea hadn't occurred to me.

So, I looked at the list she started of questions to ask each other while we FaceTime and started adding more.

Not that it isn't totally important to stay informed about everything going on in the world, but constantly talking only about how the world seems to be all bad all the time can get exhausting.

With many people now making FaceTime dates with their friends or having to use Zoom or other types of video chats to meet with WFH co-workers, here are some amiable open-ended questions you can ask each other to start the conversation or keep it going:

  1. What is your most memorable birthday?
  2. What is the best concert you've ever attended?
  3. What is your favorite memory we share together?
  4. What are three adjectives you'd want someone to use to describe you?
  5. Do you believe in luck or chance?
  6. What was the best thing that happened to you today? This week? This month?
  7. What was your favorite thing you ate today?
  8. What is the first thing you notice about a person?
  9. What was the craziest thing you've ever done for a significant other?
  10. What is the first thing you'd do if you won the lottery?
  11. What is something you like to do that other people consider weird?
  12. What decade would you have liked to have lived in and why?
  13. What is the best pizza topping combination?
  14. What is something you've always wanted to try but never had the courage to do?
  15. When do you feel like you're the most authentic you?
  16. What's your favorite thing about your best friend?
  17. If you needed to run away from everyone, where would you go?
  18. What's your most embarrassing childhood memory?
  19. What's your first memory?
  20. If money wasn't an obstacle, what would you be doing with your life?
  21. What is the best gift you've ever given? Received?
  22. What is the worst thing a parent caught you doing when you were a kid?
  23. What were your favorite things to learn about in school?
  24. If you could pick any animal to have the ability to speak, what animal would it be?
  25. What do you think is the best feeling in the world?
  26. How do you define success?
  27. What would your pet say about you if someone asked them for a reference?
  28. Where did your name come from?
  29. What is your favorite, go-to movie and why?
  30. If you could marry any Hollywood star, who would it be?
  31. If you had a choice, which would you be and why: the oldest, middle or youngest child?
  32. How have you successfully changed careers?
  33. What are your top five favorite sitcoms?
  34. How do you break the news to someone that you only like them as a friend?
  35. What's your worst breakup story?
  36. What was your first email address?
  37. What was the first CD you bought?
  38. What show do you put on while you're doing miscellaneous tasks (i.e. cleaning your room, getting ready, etc.)?
  39. Who was your first crush?
  40. Which Disney royal did you have a crush on?
  41. What's in your purse, tote bag or backpack right now?
  42. What's the most embarrassing nickname you have for your pet?
  43. Can you identify every state on a map if it wasn't labeled?
  44. What is your guiltiest pleasure?
  45. What would you tell your younger self if you could?
  46. What's the best piece of advice you've ever gotten?
  47. Where is your favorite place to vacation and why?
  48. What's something you've never told anyone?
  49. What's your cringe-worthiest interview story?
  50. What's the funniest excuse you've ever used to get out of a date?

Whether you've known each other for years or are new friends, these questions can help you learn a little something about each other. Happy conversation-starting, friends!

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