Questions to Ask Someone You Just Met Online

Conversations with strangers almost never stall because you've run out of things to ask. They stall because the question was the wrong size for the moment — something heavy in the first thirty seconds, or something throwaway twenty minutes in, when it was ready to go somewhere.

So these are sorted by depth instead of by topic. Work down as the conversation earns it.

The First Thirty Seconds

Easy to answer, impossible to get wrong, and every one of them opens a door. It's the only stage where the question matters more than the answer.

• Where are you from?
• What time is it there?
• Is it warm where you are?
• What is that behind you?
• Is this your evening or your morning?
• Have you been on here long?
• Is that your cat or are you cat-sitting?
• What are you supposed to be doing right now instead of this?

Once You Are Actually Talking

Around the two-minute mark you'll know whether there's a conversation here. If there is, these keep it moving: specific enough to get a real answer, light enough that nobody has to work for it.

• What is the best thing about the city you live in?
• What is the worst thing about it?
• What do people there do on a Friday night?
• What food should I try if I ever visit?
• What is something tourists always get wrong about your country?
• How many languages do you speak?
• What are you listening to at the moment?
• Do you work or study — and is it what you expected?
• What is the last thing you watched all the way through?
• Are you a morning person or is that a lie you tell at work?
• What is something you are unreasonably good at?
• What did you want to be when you were ten?
• What is the most useless fact you know?
• What is something everyone likes that you find overrated?

When It Is Going Somewhere

For chats that have already run a while. Asked early they're strange. Asked late, they're why people still remember a conversation with somebody they never spoke to again.

• What is something you changed your mind about in the last year?
• What is the best decision you have made recently?
• What would you do with a completely free week?
• Is there somewhere you have always wanted to live?
• What is something you are learning at the moment?
• What is the nicest thing a stranger has ever done for you?
• What do you miss about being a kid?
• What is something you have never told anyone at work?
• What would you do if money were not a factor?
• Who has had the biggest influence on how you see things?
• What is something you are quietly proud of?
• What is the last thing that genuinely surprised you?
• Is there anything you would do differently if you started over?
• What does a good life look like to you?

Four to Avoid Early

The Technique That Replaces the List

Every answer contains the next question. She says she's a nurse — that contains which shift, whether tonight's a night off, how long she's been doing it, whether it's what she expected. You don't have to think of anything new. You have to be interested in what you've already got.

Once that's a habit, lists like this one stop being necessary. Until then, four of these memorised will carry any first conversation. More on the mechanics in how to talk to girls on video chat.