Things to Ask to Get to Know Someone Better

Easy Questions That Give You Somewhere to Go Next

Early questions work best when they are specific enough to invite a story but ordinary enough that the other person does not have to decide how much of their private life to reveal. Listen for details you can follow. If someone mentions that they cook every Sunday, the natural next question may be what they like to make, who taught them, or whether they cook for other people.

These are especially useful when you have just met, when there is a lull in conversation, or when you want to move beyond weather and work without suddenly becoming intense.

1. What have you been looking forward to lately?
2. What does a really good weekend look like for you?
3. What is something you can happily spend hours doing?
4. What kind of music do you put on when you get to choose?
5. What is a place you never get tired of going back to?
6. What is something you have gotten into recently?
7. Are you more of a planner or someone who figures things out as you go?
8. What is the best meal you have had lately?
9. What is something small that reliably improves your day?
10. What is one thing people are usually surprised to learn about you?
11. What did you want to be when you were a kid?
12. What is a skill you would love to be much better at?
13. What is your favorite way to spend time outside?
14. What kind of trip sounds perfect to you right now?
15. What is something you have watched, read, or listened to that you keep recommending?

Questions About Background Without Turning It into a Biography

Background questions become more interesting when they focus on experience instead of résumé facts. “Where did you grow up?” is fine, but “What did you like about growing up there?” gives the person choices about what to share. It can lead to family traditions, hometown quirks, school memories, community, or why they eventually left.

If family is complicated, do not assume that childhood or family questions are automatically comfortable. Let the other person set the depth. A short answer is often a signal to move on rather than a challenge to dig harder.

1. What was the place you grew up in like?
2. What is a tradition from your childhood that you still like?
3. Who influenced you a lot when you were younger?
4. What were you like in school compared with who you are now?
5. What is something your family did differently from other families you knew?
6. Was there a teacher, coach, or mentor who changed how you saw yourself?
7. What is a childhood memory that still makes you laugh?
8. What is something you appreciate more about your upbringing now than you did then?
9. What did your younger self get completely wrong about adult life?
10. What is one place from your past you would like to visit again?

Questions That Reveal Values and Personality

You learn more about a person from how they make choices than from asking them to name their values. Instead of “What are your values?” ask about situations where priorities compete. The answers often reveal how someone thinks about loyalty, ambition, security, independence, generosity, risk, family, work, and time.

There is no need to agree with every answer. In fact, differences can make a conversation better when you are curious rather than trying to win. If an answer surprises you, “What makes you see it that way?” is usually more productive than immediately offering a counterargument.

1. What do you value more now than you did five years ago?
2. What is something you are willing to spend more money on because it matters to you?
3. What is something you protect your time from?
4. What kind of behavior makes you trust someone quickly?
5. What makes you lose trust in someone?
6. What does being successful mean to you right now?
7. What is a rule you used to follow that you no longer believe in?
8. When you have a difficult decision, whose opinion do you usually want?
9. What do you think people worry about too much?
10. What is something you think is worth doing even if you are not especially good at it?
11. What makes a home feel comfortable to you?
12. What do you admire most in your closest friends?

Questions That Move into Deeper Territory

Deeper questions work when there is already some trust. They are not “better” than light questions; they simply reveal different information. If the setting is right, they can turn a pleasant conversation into one you remember because both people stopped performing and started talking about what actually matters.

The safest way to deepen a conversation is often to answer first. You might say, “I have been thinking about what I want to be better at this year. What is something you are trying to improve?” That makes the exchange reciprocal instead of putting the other person under a spotlight.

1. What is something you have changed your mind about in the last few years?
2. What is a hard lesson you are glad you learned?
3. What do you wish people understood about you sooner?
4. What is something you are still figuring out?
5. When do you feel most like yourself?
6. What kind of change is hardest for you?
7. What is something you are proud of that does not show up on a résumé?
8. What relationship in your life has taught you the most?
9. What do you want more of in your life over the next few years?
10. What are you better at saying no to now?
11. What has become less important to you as you have gotten older?
12. What is a risk you took that you are glad you took?

Fun Questions That Still Tell You Something

Playful questions are useful because people often reveal preferences and personality when they are not trying to give a serious answer. They are also a good reset after a heavier topic. The best ones have enough room for explanation; a silly choice followed by “why?” can produce a surprisingly good story.

1. If you could become excellent at one hobby overnight, what would you pick?
2. What is your most defensible unpopular food opinion?
3. If you had to live in one season all year, which one would you choose?
4. What ordinary thing are you strangely particular about?
5. What is a purchase under fifty dollars that improved your life?
6. If you could rewatch one movie for the first time, what would it be?
7. What is a completely unnecessary thing that brings you joy?
8. What is the funniest misunderstanding you have been part of?
9. If someone gave you an unexpected free day tomorrow, how would you spend it?
10. What is a harmless hill you are willing to die on?

How to Make the Conversation Feel Natural

Do not work down the list in order. Pick one question that fits what is already happening, then stay with the answer. Good follow-ups often begin with a detail the person volunteered: “How did you get into that?” “What happened after that?” “Was that an easy decision?” “What do you like most about it?” These questions communicate that you were actually listening.

Share your own answer when it helps. If you ask about a favorite trip, mention yours after they answer. If you ask about a difficult lesson, be willing to offer one of your own if the conversation reaches that depth. Mutual disclosure is one of the clearest differences between a conversation and an interview.

Watch for short answers, topic changes, nervous humor, or a person repeatedly giving general rather than specific responses. You do not need to diagnose why. Simply move to a lighter subject. Curiosity is useful only when the other person has room to choose what they want to share.

Questions to Avoid Too Early

There is no universal list of forbidden subjects, but some questions carry more emotional weight than they appear to. Detailed questions about income, debt, fertility, health conditions, trauma, divorce, religion, politics, family estrangement, or sex can be appropriate in some relationships and intrusive in others. Context matters more than the existence of the topic.

Also avoid assumptions hidden inside questions. “Why are you still single?” assumes being single requires an explanation. “When are you having kids?” assumes plans and circumstances that may be private. “What do you really do for a living?” can accidentally turn work into a status test. If you are genuinely curious, choose neutral wording and let the person decide how much detail to offer.

Adjust the Questions to How You Know the Person

The same question can feel easy in one setting and odd in another. With a coworker you have just met, asking what they like to do outside work is usually natural; asking what they fear most may not be. With a longtime friend, a question about what they want from the next five years may be completely normal. The relationship gives the question its meaning.

With a New Friend

Look for shared interests and routines that could lead to spending time together again. Questions about favorite local places, hobbies, weekend habits, food, events, and things they have been wanting to try create easy openings for future plans. If you discover that both of you like live music, hiking, trivia, or trying new restaurants, the conversation has given you a practical next step.

With a Coworker

Keep the first layer low-pressure. Ask how they got into their field, what they enjoy about the work, what part of the city they know best, or what they do to switch off after work. Avoid putting them in a position where they have to discuss compensation, office politics, family plans, or personal beliefs before you have that kind of relationship.

With Someone You May Want to Date

You can move toward values and lifestyle a little sooner because compatibility matters, but the conversation should still feel mutual. Ask how they like to spend time, what relationships are important to them, what they are excited about, and what they are hoping dating leads to. For a specifically romantic setting, the first-date questions page goes further into compatibility without turning the evening into a screening interview.

Five Follow-Ups That Work with Almost Any Answer

You do not need dozens of clever follow-ups. A small set of natural prompts can keep a good topic going without sounding rehearsed.

1. How did you get into that?
2. What do you like most about it?
3. Was that always the plan?
4. What surprised you about it?
5. Would you do it the same way again?

Use them selectively. If the other person is animated and giving detail, a follow-up shows interest. If the answer is short or they immediately change subjects, let the topic go. Being good at conversation includes recognizing when not to ask another question.