Questions to Ask Someone: Good Ones That Get a Chat Going

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Good questions to ask someone are open ones that invite a story, followed by a second question about their answer. Match the mood, share a bit of yourself too, and a chat never feels like an interview.

What makes a question good in a chat?

A good question is easy to answer and hard to answer in one word. It gives the other person a little stage: room for a story, an opinion or a daft detail you can pick up on.

Closed questions get a yes or a no, and a chat stalls unless someone works hard to restart it. Open ones start with what, how, which or "tell me about", and hand the other person something to run with.

Closed: a full stop

Do you play any sport?
Do you like the outdoors?
Are you a morning person?

Open: a way in

What's a sport you'd try if nobody was watching?
Where's the last place you went that left you muddy and happy?
What's usually the first good moment of your day?

Specific beats general, too. "Where are you from?" has been answered a hundred times. "What would you show a visitor to your town on a sunny day?" is about a real place, so the answer comes out fresher.

Why is the follow-up the real question?

The first question opens the door. The second, about what they've just told you, proves you were listening, and that's usually where a chat warms up.

It doesn't need to be clever: pick one detail and ask why, how it started or what happened next. Here's a made-up example of how that can go:

Where's the last place you went that left you muddy and happy?
A hill race last weekend. I came second to last.
Who came last, and are you still friends?
My brother. And only just.

That second question came straight out of the answer, not from a list, and it's the habit worth building. There's more on this in how to keep a conversation going.

How do you match the mood of a chat?

The same question can land beautifully in one place and fall flat in another, so read the room before you ask. Literally, if you're in one.

A busy room
Keep it light and quick: a would you rather or a this or that anyone can answer in a line.
A one-to-one chat
Now there's space for stories. Ask about their week and their plans, and give your own answers too.
A late, quiet natter
Slower evenings suit thoughtful questions. Go deeper only if they're going there too.

How do you ask questions without it feeling like an interview?

Fire off five questions in a row and a lovely chat starts to feel like a job application. These habits keep it a conversation.

Answer your own question: Ask, listen, then share your version. It's fairer, and it gives them something to ask you back.
One big question at a time: Send three in one message and they'll answer the easiest. The other two quietly vanish.
Follow the tangent: If their answer wanders somewhere more interesting than your next question, go with it. The list will keep.
Not every message needs a question mark: Sometimes "ha, that's brilliant" is the right reply, and they'll carry it on from there.

Question games and lists to try tonight

Would you rather questions
130 either-or dilemmas, from funny and food to deep, plus how to play them in a chat.
Questions to ask a guy
110 questions for chatting, texting and first dates, and how to read his answers.
21 questions game
The simple rules, how to play over text and five ready-made sets of 21.
This or that questions
126 quick-fire picks for a busy room, and how to turn a pick into a proper chat.
Deep questions to ask
Questions that get past small talk, and when to ask them.
First date questions
What to ask on the night, and what to save for later.

Where can you put these questions to use?

Natter is for adults, 18+, who fancy a good natter: some come for friendship, some hope for a date, and some don't mind which. The chat rooms, which admins moderate, suit the quick games. Private messages suit the slower, one-to-one questions.

For a first line rather than a whole conversation, try the icebreaker questions. The how to chat guides cover everything from hello to keeping things going, and the flirting guides help when a chat turns a little flirty.

Questions about asking questions

What are good questions to ask someone you've just started chatting to?

Ones about what they're doing and enjoying right now: their week, a hobby, a place they love. They're easy to answer, they invite a story, and they give you something to ask about next.

Which questions are better saved for later?

Money, past relationships in detail, and exactly where someone lives or works can all wait until you know each other well. Never ask for bank details or share your own, and keep your address to yourself until you're sure about someone; the chat safety guide explains why.

Do these questions work for making friends too?

Yes. Most good questions suit any kind of chat, and Natter is as much about friendship as it is about dating. The flirtier ones are clearly labelled, so you can save them for chats where the mood is right.

Can I play question games in the chat rooms?

Yes, in the rooms open to you. Quick games such as would you rather or this or that suit a busy room, while deeper questions work better in private messages. Keep it friendly and let people skip a question they'd rather not answer.

Got a Good Question? Come and Ask It

Make a profile, find a room that suits your mood and see who wants to answer.