To get to know someone, ask questions that invite stories instead of facts, and increase depth gradually. Start light ("What have you been into lately?"), move to experiences ("What was the best part of that?") and only then to values ("What matters most to you in your work?"). Listening to the answer matters more than the question.
Depth ladder instead of a giant list
Most lists of 100 questions fail because they ignore timing. A deep question to a near stranger feels intrusive. A shallow question to a friend of years feels flat. Use three levels and let the other person's answers tell you when to go deeper.
| Level | Feels like | Good for |
|---|---|---|
| 1. Light | Easy, fun, no pressure | New acquaintances, parties, first chats |
| 2. Personal | Stories and preferences | People you have met a few times |
| 3. Meaningful | Values, plans, lessons | Friends, close colleagues, trusted people |
If you need the very first line, see conversation starters. This page picks up once the chat has started and you want to learn who the person is.
Level 1: light questions
These are easy to answer and set a friendly tone.
- What have you been into lately: a show, a podcast, a hobby?
- What is the best thing you ate this week?
- Do you have a go-to spot in this neighbourhood?
- What would you do with a free Saturday?
- Are you a morning person or a night person?
- What is something small that always makes your day better?
Light does not mean empty. These questions often reveal interests you can follow later.
Level 2: personal questions
Use these once there is a little trust, or when the person is clearly happy to talk.
- How did you end up doing what you do now?
- What did you like about the place where you grew up?
- What is something you taught yourself recently?
- What was your favourite trip, and what made it good?
- Who is someone who influenced how you think?
- What is a hobby you would try if you had more time?
Stories surface here. When you hear one, stay with it: "What was that like?" is often better than moving to a new topic. See active listening for how.
Level 3: meaningful questions
Save these for people you know or when the conversation is already open and warm.
- What do you wish more people understood about your work or life?
- What has been a turning point for you?
- What are you looking forward to this year?
- What does a good life look like to you right now?
- What is something you are proud of that you rarely mention?
- What would you tell your younger self?
If someone hesitates or gives a short answer, step back a level. No one has to answer, and a relaxed "no pressure" keeps the mood safe.
Questions by setting
| Setting | Question | Level |
|---|---|---|
| New colleague | "What was your path to this team?" | 1-2 |
| Friend of a friend | "How do you two know each other?" | 1 |
| Date or one-to-one meeting | "What do you do when you are not working?" | 1-2 |
| Group or club | "What got you into this hobby?" | 2 |
| Long-time friend | "What is on your mind lately?" | 3 |
For making friends specifically, see our guide to making friends.
How to ask well
Ask open questions. Start with "what", "how" or "tell me about". "Do you like your job?" gets a yes or no. "What do you like most about your job?" gets a story.
Be curious, not clever. People can tell when you are collecting facts versus actually interested. Pick questions you would be glad to hear the answer to.
Share back. After someone answers, offer a short piece of your own. "I'm the same, I learnt to cook during a long winter." Then ask again. Alternating keeps it a conversation, not a questionnaire.
Follow the thread. The best next question is usually inside their last answer. If you rely on a script, you may miss it. For more on this, see how to keep a conversation going.
Let silence work. Pausing for a few seconds after an answer often leads someone to add something more honest.
Questions to avoid
- Questions that sound like a job interview ("Where do you see yourself in five years?") unless you are in that context.
- Questions about money, health or relationship status with someone you barely know.
- Questions with a built-in judgement ("Why haven't you moved out yet?").
- Rapid-fire questions with no pause for your own comments.
Practising question-asking
You get better at questions the same way you get better at everything social: small, regular practice. Try one new open question per day for a week with a colleague, neighbour or shop assistant. Note which questions lead to longer answers. You can plan lines with the what to say tool.
If you want a structure, Solo Era is an iPhone app with small real-world missions, including a level 1 "people" mission, "Ask a staff member one genuine question." You rate how nervous you felt before and after so you can see the pattern. It is a practice nudge, not a question generator, and it is not therapy. Free to download. A subscription is required to start missions. Prices and any free trial depend on the offer and eligibility shown in the app.
Solo Era for iPhone
Try it with Solo Era
Solo Era gives you one realistic mission a week, records how nervous you felt before and after, and keeps a photo journal of what you did. An iPhone app. A subscription is required to start missions; any free trial depends on the offer and eligibility shown in the app.
Keep reading
- What to Do When You Run Out of Things to Say: Quiet moments are normal. Use follow-up questions, observations and topic bridges to restart a stalled conversation, or end it gracefully when it is done.
FAQ
What are good questions to ask someone you just met?
Light, open questions about the shared setting or their interests: "What brought you here?", "What have you been into lately?" They are easy to answer and make a chat feel natural.
How do I ask deeper questions without being awkward?
Go in steps. Begin light, listen for a personal detail, and then ask about it. If they respond openly, you can go a level deeper. If not, stay where you are.
How many questions are too many?
If it starts to feel like an interview, add your own stories or comments between questions. A good ratio is roughly one share for every question or two.
What if the other person does not ask me anything?
Offer small shares and see if they ask back. Some people are shy or less practised at asking. You can still enjoy the conversation and decide later if you want to continue the connection.
Can I use these questions with friends and family?
Yes. Level 2 and 3 questions are especially good for people you already know, where they can lead to conversations you have never had.
Solo Era for iPhone
Try it with Solo Era
Solo Era gives you one realistic mission a week, records how nervous you felt before and after, and keeps a photo journal of what you did. An iPhone app. A subscription is required to start missions; any free trial depends on the offer and eligibility shown in the app.
