50 Fun Questions to Ask Someone on Video Chat

The first line is the hardest. After that, you just follow where it goes. Bookmark this list and pull one out whenever a chat needs a spark — they are sorted from light and easy to a little more real, so you can match the mood.

Easy openers (zero pressure)

1. What has made you smile today?
2. Coffee, tea, or something else entirely?
3. Where are you tuning in from?
4. Cats or dogs — and defend it.
5. What is playing on repeat for you right now?
6. Sweet or savory snacks?
7. What time is it where you are?
8. Beach trip or mountain trip?
9. What is the weather doing outside your window?
10. Night owl or early bird?

Fun and a little random

1. If you could teleport anywhere right now, where would you go?
2. What is a weirdly specific skill you have?
3. What is the last thing that made you laugh out loud?
4. What is your most-used emoji?
5. What fictional world would you live in?
6. What is your comfort movie?
7. What is the best meal you have had this month?
8. If you had a warning label, what would it say?
9. What is a hill you will happily die on?
10. What is the strangest thing within arm’s reach right now?

Getting to know them

1. What are you weirdly passionate about?
2. What is something you have changed your mind about lately?
3. What did you want to be as a kid?
4. What is a small thing that instantly improves your day?
5. What is something you are proud of but never mention?
6. What is your go-to way to unwind?
7. What is a place you have always wanted to visit?
8. What is the best advice you have ever gotten?
9. What are you looking forward to this week?
10. What is a hobby you would pick up with unlimited time?

Playful "would you rather"

1. Would you rather always be 10 minutes early or 20 minutes late?
2. Would you rather never use a phone or never use a laptop again?
3. Would you rather explore space or the deep ocean?
4. Would you rather have free flights or free food for life?
5. Would you rather relive your best day or skip to a great future one?
6. Would you rather be fluent in every language or master every instrument?
7. Would you rather live in a big city or a tiny town?
8. Would you rather have too much free time or too much money?
9. Would you rather be able to fly or be invisible?
10. Would you rather always know when someone is lying or always get away with lying?

A little deeper (only if it is clicking)

1. What is something you are grateful for today?
2. Who has had the biggest influence on who you are?
3. What does a genuinely good day look like for you?
4. What is a fear you have mostly gotten over?
5. What is something you wish more people understood about you?
6. What is a moment that changed how you see things?
7. What are you working toward right now?
8. What is the kindest thing a stranger has ever done for you?
9. What would you tell your younger self?
10. What makes you feel most like yourself?

You will never get through all fifty in one chat — and that is the point. Pick one, follow where it goes, and if the conversation is not landing, skip to the next person and start fresh.