Questions to ask a new online friend#

The internet has no shortage of questions to ask a new friend. There are lists of 50, 200, 371. At some point you're less a person having a chat and more a customs form with feelings.

The problem usually isn't a shortage of questions. It's that a question can be perfectly respectable and still land like paperwork:

What are your hobbies?

What kind of music do you like?

Where do you see yourself in five years?

Nothing wrong with any of those. But stack them together and the other person has to keep producing answers while you stand there with a clipboard.

Bring something with the question#

The easiest improvement is to stop sending questions alone.

React to something the person said, add a little of your own experience, then ask about the part you're genuinely curious about. For example:

You mentioned restoring old furniture. I love hobbies where you can point at a solid object afterwards and say "I did that" - most of my work disappears into a computer. What's the best thing you've rescued?

Now they know why you're asking, and have a few possible things to pick up: the furniture, making things, computer work, a specific rescue. You haven't just handed them an assignment.

This is especially useful in text, where a flat question has no warm tone of voice attached to save it.

A few questions that can actually go somewhere#

Please don't fire these at someone in order. Pick one if it fits the person or the chat you're already having, then pay attention to the answer.

Good early questions:

What's something you've been quietly looking forward to?
What have you been oddly interested in lately?
What's the last thing you made, fixed, cooked, grew, or figured out?
What could you happily give a twenty-minute unprepared talk about?
What's something popular that you tried very hard to like?
What's a recommendation you keep trying to give people?

That last one is useful. You may leave with a book, film, recipe, obscure podcast, or strong warning about a particular brand of cordless drill.

Questions that might produce a story rather than a fact:

When have you been completely wrong about a person, in a good way?
What's something you learned much later than everyone else seemed to?
Have you ever had a hobby get slightly out of hand?
What's a kindness from a stranger that you still remember?
What was your first little corner of the internet?

"Do you travel?" gets yes or no. "What trip went most unlike the plan?" has somewhere to go. And if somebody tells you about getting lost in Istanbul, you do not need to consult question 86. Istanbul has done the work for you.

Once you already know each other a little:

What's something you've changed your mind about in the last few years?
What do people tend to misunderstand about you?
What are you trying to get better at, apart from work?

Don't force a new chat to become deep. Give it time, and leave people an easy way not to answer. If somebody gives you a sincere answer and you reply "cool lol, next question", the list cannot help you.

Silly questions are underrated too:

What utterly pointless thing are you unusually good at?
If your home had a secret room, what would you put in it?
What food opinion would get you expelled from your country?

Not every chat needs to march bravely toward the meaning of life. Sometimes you just need to establish the correct position on pineapple.

Questions that aren't really questions#

Some questions are requests for reassurance, tests, or pressure wearing a question mark:

"Why didn't you reply?"
"Can I see what you look like?"
"Are you single?"
"What's your real name?"
"Why won't you move to another app?"

If somebody hasn't offered personal information, don't keep circling it with increasingly ingenious grammar. Curiosity is interest in another person; pressure is interest in getting what you want from them. People can feel the difference.

And don't ask a deep question merely because you want to give your deep answer. If you're waiting impatiently for them to finish so you can deliver your monologue, you didn't ask. You requested a cue.

One good follow-up beats ten clever openers#

The best question in a chat is usually not on any list. It's the one that follows naturally from what the person just told you.

Notice the detail with a little life in it. Ask about that. Remember the answer. Bring it up next week.

People often really want to connect but freeze at the blank screen, which is why I built Topic Tango for Wusoup. It gives two people a topic they both agreed to talk about. Sometimes that little push is all a chat needs.

Use a question here if it helps. Then put the list away and talk to the person.