Fun Questions to Ask Strangers on Random Video Chat

A good question does more work than a great opener. These questions are built for random video chat: quick to answer, hard to answer badly, and likely to give you something to follow up on.

Questions That Get People Talking

The best questions for a video chat with strangers share three traits. They can be answered in a sentence, they invite a story rather than a fact, and they are not personal in a way that feels like an interrogation. Skip anything about where exactly someone lives or works.

Here are some that tend to work:

• What is something you are weirdly good at?
• What did you eat today that you would recommend?
• If your town had an honest tourist slogan, what would it be?
• What is a song you can never skip?
• What is the best thing you learned this year?
• Which small thing in your room has the best story?
• If you could swap jobs with anyone for one week, who would it be?

Notice that none of these fun conversation starters are yes or no questions. Asking “Do you like music?” gets one word, while asking for a song gets a name, a reason and usually a memory.

The object question is especially good in a video chat, because your partner can hold the thing up. Suddenly you both have something to look at besides each other’s faces, and the story behind it does the rest.

How to Ask So the Answer Goes Somewhere

Even the best questions to ask strangers are only half the move. The other half is the follow-up, and that is where a random chat becomes a conversation. If someone says they are weirdly good at parallel parking, ask how they found out, not what else they are good at.

Go easy on rapid fire. Five questions in a row make the call feel like a quiz show. Ask one, react, share your own answer, then let them choose where to go. Parlour games like the Proust Questionnaire were played in turns, and the same rule holds on camera: questions feel friendly when you answer them too.

Read the room as well. If your partner gives short answers to two questions in a row, they may be tired, shy or busy, and that is not a puzzle you need to solve. Thank them and move on. For more on pacing, our video chat tips cover openers and awkward silences.

When you are ready to try a few, start a video chat with one question in mind. The right live video chat partner will hand you three more.