Interesting Questions to Ask

Asking questions is a great way to get a conversation going. However, by formulating or following up with cool and interesting questions to ask people, you can often move the interaction past everyday small talk and get right to sharing and connecting on a deeper level.

But when is the right time to introduce deeper, more interesting questions to the conversation? The simple answer to this is when it feels right. Often, conversations will naturally lead to deeper places, where something they say, almost out of social etiquette, demands a more interesting, thought-out follow-up. Alternatively, you may find that you’re running out of small talk options and urgently need to take the conversation to a more engaging level.

Bringing up the right interesting questions to ask someone can help people get more involved in the conversation, inspire them to invest in a positive outcome and add fascinating new dimensions to the interaction, making it seem deeper and more personal. These questions make you seem cooler and socially at ease in conversation.    

Interesting questions come in a variety of forms, depending on the tone you want to strike and how well you know the person. They can include interesting ice breakers you can use on a stranger, ones you can ask friends, ones that work with connecting with your crush or even interesting questions that are designed to elicit a response on dating apps. Let’s explore these types of interesting questions to ask others and why they work so well.

Interesting questions to use as conversation starters

Interesting conversation starters are a more engaging way to break the ice with a stranger or just someone you don’t know very well yet.

These scripts are useful because many interactions in our day are routine and don’t need complete mental engagement. Coming up with interesting questions to ask a stranger or even a cool conversational prompt can often help break people out of their usual scripts.

However, it can sometimes be risky or even overwhelming for shyer or more reserved people. So, it’s important to come up with interesting questions that are more entertaining, such as a humorous observation of your surroundings – than overly deep or personal ones.

Here are some you can use either as a way of starting the conversation or shortly after introducing yourself.

1. What’s something you’ve recently learned that surprised you?
2. If you could master one random skill overnight, what would it be?
3. What’s a simple thing that always makes your day better?
4. If you could live anywhere for a year, where would it be and why?
5. What’s something small you’ve done lately that made you proud?
6. If your week had a theme song, what would it be?
7. What’s a topic you could talk about for hours without getting bored?
8. What’s a childhood dream you never quite let go of?
9. What’s a hobby you admire but never tried?
10. If you could trade places with someone for a day, who would it be?
11. What’s a movie or book that made you see life differently?
12. What’s your favorite way to spend a Sunday morning?

Interesting questions to ask to get to know someone

These are the kind of interesting questions to ask early on in your interactions, as they help reveal certain key facts and aspects of the person you’re talking to and express curiosity about them. They may seem a bit boilerplate, as we tend to explore people sequentially, first looking at external interests and thoughts, while slowly working toward the core of a person until you begin to ask about internal aspects of their inner passions and dreams for the future.

They may be repetitive, but they’re necessary if you want to really know someone and build intimacy. By asking more interesting get to know you questions, you get to gather the same kind of personal information you need and decide whether there’s any compatibility there while approaching it from a more novel conversational angle. 

Use their answers and how open they are with you to guide you on which kinds of questions they’re comfortable sharing about. Here are a few you could try. 

13. What’s a value or belief that’s really important to you?
14. How do you usually spend your free time?
15. What’s something you’re currently working on about improving yourself?
16. What’s a decision that changed your life unexpectedly?
17. If you could relive one moment, just to experience it again, what would it be?
18. What’s a small daily ritual that makes you happy?
19. Do you find it easy or hard to open up to people?
20. What do you think people first notice about you?
21. What kind of person do you find easiest to connect with?
22. What’s a dream or goal that still feels exciting to you?
23. What do you think makes a conversation meaningful?

Good interesting questions to ask

A good, interesting question is the kind that doesn’t simply gather information but also creates a cool, emotionally interactive experience simply in the act of answering and exploring the topic more. What’s considered good can vary from person to person but in general, people tend to enjoy questions that are somewhat unique and express a deeper curiosity about them, searching beneath the surface. 

A well-thought-out, interesting question can help infuse the conversation with vibrant energy, making the interaction a more entertaining experience. It casually encourages the other person to put thought into their answer, possibly revealing aspects of themselves they wouldn’t ordinarily share so early in the relationship.

Interesting questions can be used at any point in a conversation. However, you’ll want to use them sparingly because just as they can bring renewed energy to a conversation, they can also sometimes pivot it away from a topic that was already on a good track. Consider these examples for guidance.

1. What’s a memory that always makes you smile?
2. What’s the best compliment you’ve ever received?
3. What do you find most inspiring about the people you admire?
4. If money and time weren’t a concern, what would you do tomorrow?
5. What’s something you used to believe that you’ve since changed your mind about?
6. What’s a little thing that brings you peace?
7. What’s your most interesting or unusual habit?
8. If you could instantly learn another language, which one would it be?
9. What’s a random skill you’d love to show off?
10. Who’s someone you look up to, and what have they taught you?

Interesting questions to ask a man

You may be wondering if there are certain types of interesting questions to ask a guy that you wouldn’t ask a woman. Well, not really. Men and women tend to enjoy discussing quite similar topics, like hobbies, interests and experiences. What is often different is how men and women approach social relationships. 

A study in the Journal of Economic Behavior & Organization found that while men are very social and tend to build a wide network of relationships, these networks often tend to be less cooperative and stable than women’s.¹ Men are often more preoccupied with how cool and confident they come across in interactions. This isn’t necessarily by design but a cultural norm, so it can be overcome.

You can do this by coming up with interesting questions to ask a boy that builds a greater sense of intimacy and creates a stronger bond. In doing so, you help distinguish yourself from their other social connections and foster a tone of trust and support in your relationship rather than an initially competitive one. Try these at first and use their answers to come up with more personal questions.

1. What’s a challenge that shaped you into who you are today?
2. What kind of adventures do you want to have more of?
3. What’s something you’re passionate about that people wouldn’t guess?
4. What’s your definition of confidence?
5. What’s one thing that instantly motivates you?
6. What’s the best advice you’ve ever received from another man?
7. If you could redo one decision in your past, would you?
8. What does a good day look like to you?
9. What’s a personal goal you’re working toward right now?
10. What’s something that never fails to make you laugh?
11. What’s a song or quote that really resonates with you?
12. How do you usually celebrate your small wins?

Most interesting questions to ask a woman

These are questions that are more suited to how women approach their relationships and everyday interactions. The same study as above, conversely, showed that women emotionally invest more deeply in their relationships and seek to maintain harmony.²

But this can be a double-edged sword because just as women tend to be more open and agreeable, they also tend to make it less obvious when questions cross a boundary or when a topic of conversation is displeasing to them.

When thinking up some interesting questions to ask a girl, put yourself in their shoes and ask yourself whether you’d be comfortable or engaged if the question were posed to you. It’s a good idea to pay attention to their body language when answering certain questions. If they’re feeling comfortable, they’ll often physically open up to you by making more eye contact, opening their posture and leaning in slightly while they talk.

Here are a few examples of more female-oriented questions. Although most of these would also be engaging to men in certain cases.

1. What’s something you’re deeply passionate about?
2. What’s the most adventurous thing you’ve ever done just for yourself?
3. If you could give your younger self one piece of advice, what would it be?
4. What kind of experiences make you feel most alive?
5. What’s a creative outlet that helps you unwind?
6. What’s something you wish people asked you more often?
7. Who inspires you to be the best version of yourself?
8. What’s your favorite way to express your personality?
9. What’s a small detail in life that makes you happy?
10. What’s a dream destination you’d love to visit one day?
11. What do you find most attractive about someone’s personality?
12. What’s something you’ve learned about yourself in the last year?

Interesting questions to ask friends

Questions that are more geared towards platonic relationships, creating healthier bonds between existing friends and fostering deeper connections more naturally with new ones. Coming up with some interesting questions to ask friends is often more crucial than it is in dating.

Dating is very much a shaped interaction with well-defined goals. You get to know each other, establish whether there’s chemistry and overall compatibility, and decide whether you want to continue seeing each other to keep up the process. Friendships are sort of shapeless. You can become closer friends or simply remain friendly acquaintances. There’s a greater onus on you to purposely develop the relationship. Asking interesting questions is a cool way to achieve this in a way that feels organic and not overly familiar.

Friendships tend to grow at a more gradual pace, so try not to bombard a friend with too many questions in a single conversation. Instead, you can try and pepper these examples in your everyday interactions with them or when there’s an obvious dip in the conversation.

1. What’s your favorite inside joke we have?
2. What’s something new you’ve learned recently that fascinated you?
3. If we could take a spontaneous trip anywhere, where would we go?
4. What’s a silly memory that never fails to make you laugh?
5. What’s something you’ve always wanted to learn, but haven’t yet?
6. If you could time travel to any era, which would you pick?
7. What’s your weirdest but most useful talent?
8. What’s your favorite way to spend a weekend with friends?
9. What’s a small gesture that means a lot to you?
10. If you could relive one day we’ve spent together, which would it be?

Interesting personal questions

Personal questions probe aspects of the person you’re talking to, from superficial things like their career and outward appearance to deeper concepts, like their outlook on the world or personal philosophies. By making these personal questions more interesting, you can turn this basic fact-gathering exercise that’s routine in human relationships into a more engaging and vibrant experience.

Personal questions have two main benefits. The first is obvious: the better you know someone, the more you understand them and how they like to interact. The second is more psychological. Studies have found that just the act of sharing information about yourself with someone makes you like that person more. It similarly found that by reciprocating and sharing information about yourself, you increase the likelihood of someone liking you.³

Personal questions are useful at any point during the interaction, if they don’t cross a boundary.  They tend to be quite neutral and indicate interest in the other person. Even in a long-term relationship, personal questions are a good way to check in with your partner and grow with them as a person.

Try out one of these questions in your next conversation with somebody in your life.

1. What motivates you to keep going when life gets difficult?
2. What’s something you’ve learned about yourself through relationships?
3. Do you think you’re more of a thinker or a doer?
4. What does happiness look like for you right now?
5. What’s one thing you’re currently grateful for?
6. What kind of environments help you feel most at peace?
7. What’s a personal habit you’re proud of developing?
8. When do you feel the most confident in yourself?
9. What’s something you’re still figuring out in life?
10. How do you usually handle moments of uncertainty?

This or that questions only have two possible answers. It can be a yes or no question or simply testing one option against another. For instance, do you prefer chocolate or vanilla? These are inherently close-ended questions, which we generally advise against. However, by finding the right kind of interesting binary questions to ask somebody, you can quickly glean important facts about them that can help you steer your questions toward more engaging topics.

These are great questions for quickly establishing compatibility without needing to have a whole conversation about it, making them particularly useful on first dates or when you’re connecting with someone over text.

You should ask this or that questions sporadically and never one after the other. Otherwise, the conversation may start to feel like an interrogation or distinctly one-dimensional. Think of them as little hints that can help tell you which open-ended questions they would enjoy. If you can’t think of any right now, here are a few cool ones you could try.

1. Would you rather explore outer space or the deep ocean, and why?
2. Would you rather spend a year traveling the world or one year mastering a new skill?
3. Would you rather always be early or always be perfectly on time?
4. Would you rather have an unlimited library or unlimited plane tickets?
5. Would you rather relive your favorite day or skip your worst one?
6. Would you rather live somewhere quiet or somewhere full of energy?
7. Would you rather have endless creativity or endless curiosity?
8. Would you rather be known for your humor or your kindness?
9. Would you rather meet your younger self or your future self?
10. Would you rather spend a day in total relaxation or total adventure?

Silly interesting questions

Silly and fun interesting questions use humor as a way of connecting with another person. Funny questions come in all shapes, from typically serious questions with a humorous twist to just plain whimsy, where there’s no informational goal but simply a desire to entertain the other person.  

Coming up with interesting funny questions to ask someone you want to grow closer with lets you take advantage of the powerful bonding aspects of humor to create a shared experience. Humor has psychological functions too, helping people to relax their social boundaries and share more openly.⁴ By focusing on making your interactions entertaining, you’ll create a positive association in their mind of the idea of spending time with you.

A light, humorous tone is ideal when you’re trying to grow closer to someone and should be a natural part of the conversation. But you can’t create that tone simply by asking silly questions. Try to use questions like the ones below to get things started or to test the waters to get a better understanding of their sense of humor.

1. If you could have a superpower that only worked on weekends, what would it be?
2. What’s the most random item you’ve ever bought online?
3. If your pet could text you, what’s the first thing it would say?
4. If you had to make up a ridiculous holiday, what would it celebrate?
5. What’s your most absurd but lovable habit?
6. If your laugh had a theme song, what would it be?
7. What’s the weirdest food combination you actually enjoy?
8. If your personality were a flavor, what would it taste like?
9. What’s a small mistake you made that turned into a funny story?
10. If you had to write a comedy sketch about your life, what would the title be?

Interesting life questions

Life questions are similar to personal questions except they tend to focus less on the contents of someone’s existence and more on their view of important life issues, their values and how they see the world. The answers to these questions are not only important when trying to gauge how compatible you two would be long-term, but they open up the scope of the conversation to explore grander and more meaningful topics beyond the territory of small talk and getting-to-know-you chit chat.

Life questions are useful because they intrinsically involve people sharing their personal outlook and feelings on things without you needing to ask them directly. This can help the other person to lower their guard a bit and share on a more intimate level.

The great thing about these questions is that they’re engaging and come across as cooler in conversation, so you can ask them at any point. People naturally enjoy sharing how they interpret the world.

If you can’t think of where to start, try one of these questions and see where the conversation takes you.

1. What’s something you’ve learned about happiness recently?
2. Do you think everything happens for a reason, or do we give things meaning later?
3. What’s one lesson you hope to never forget?
4. If you could talk to your future self, what would you ask?
5. What’s something that’s changed the way you see the world?
6. What’s your personal definition of success?
7. What makes life beautiful for you?
8. What’s a challenge that taught you more than you expected?
9. Do you think people ever truly stop growing?
10. What’s a memory you’d never trade for anything?

Interesting questions to ask someone you like

People tend to tread very carefully when it comes to talking to someone they like. Coming up with just the right interesting questions to ask your crush is something human beings often overthink to the point that it can paralyze them from moving forward. This phenomenon is known as the paradox of choice and it can take various shapes in our daily life.⁵

Interesting questions make this period of uncertainty, where you’re trying to make a strong impression without being too forward or aggressive, easier because they’re non-committal. They take the conversation to deeper topics, are lightly flirtatious and indicate positive interest while maintaining emotional distance. That is, you grow closer to the person without necessarily explicitly revealing your feelings.

Making your romantic intentions clear to your crush is a crucial part of moving the interaction forward, so don’t depend on interesting questions too much to build your bond. Try using one of these examples as a natural springboard into more romantic topics, once you’ve gauged how open they are to a specific idea.

1. What’s a little thing that always makes you smile?
2. What kind of moments make you feel the most connected to someone?
3. What’s your idea of a perfect evening?
4. What’s something you find unexpectedly attractive in a person?
5. Do you think chemistry happens instantly or builds over time?
6. What’s a hobby or interest you’d love to share with someone special?
7. What’s the best date you’ve ever been on and why did it stand out?
8. What kind of humor always gets you laughing?
9. What’s something you’ve always wanted to try with a partner?
10. What’s your idea of a strong, lasting connection?

Interesting questions to ask on a first date

First date questions are often quite goal-oriented, touching on familiar topics like their interests, values and lightly personal aspect of their life. People are this purposeful on first dates due to a combination of things like nerves, lack of rapport and a desire to avoid wasting our time on connections that aren’t going anywhere.

But this style of questioning generally doesn’t lead to a particularly romantic or compelling first date. By coming up with some interesting questions to ask beforehand, you can help settle your nerves by lightly rehearsing the interaction, create a topical fallback if the conversation runs a bit dry and find questions that are both engaging and information-oriented.

Interesting questions can lead to great conversations on first dates if they are used in moderation. You want to seem cool, indicating general interest and curiosity, not create an interview dynamic. If you start getting dry or enthusiastic responses to your questions, try to pivot to a new topic until the conversation picks up again. You can try one of these questions to start off with.

1. What’s a small thing that makes you feel appreciated on a date?
2. What’s something you’ve done recently that made you proud?
3. What’s your go-to comfort meal after a long day?
4. If you could plan your ideal weekend, what would it look like?
5. What’s something that instantly makes you like someone?
6. Do you enjoy spontaneous plans or well-thought-out ones?
7. What’s the most interesting place you’ve ever visited?
8. What’s a fun memory that still makes you laugh?
9. What’s one thing you’re currently excited about in your life?
10. What’s a movie or song that you think says a lot about you?

Interesting questions to ask on a second date

Second date questions are quite different from the ones you ask on first dates. By now, you should have gotten past most of those getting-to-know-you questions and have established at least some rapport or chemistry, which should make the atmosphere more relaxed and open. This is a good time to begin exploring deeper and more personal questions. 

Things may still feel a bit stiff between you, though, so finding interesting questions to ask lets you build off the momentum of your first date and deepen your connection. If you were listening actively during your first date, you can use what you learned to inform interesting personal questions for your second, now that they know you a bit better and have softened their boundaries somewhat.

Even more so than on the first date, you shouldn’t depend on questions too much to create conversation. Instead, use them judiciously to add energy to an already vibrant conversation, inquire about deeper personal aspects or when you simply steer the conversation to a more mutually engaging topic.

Here are a few questions you can ask on your second date.

1. What’s something you’ve always wanted to learn, and why?
2. What’s a random skill you have that surprises people?
3. What’s a passion project or hobby you’re exploring lately?
4. What kind of travel experience would you love to have one day?
5. What’s the best compliment someone could give you?
6. What’s something small that makes you feel happy during your week?
7. Do you think shared values or shared humor matter more in dating?
8. What’s the most interesting goal you’ve set for yourself recently?
9. What’s your favorite way to unwind after a long week?
10. If you could relive one perfect day, what would it be like?

Interesting questions to ask on a dating app

When it comes to interesting dating app questions, the best approach can be very different from real life or even other online interactions. Dating apps are a service that helps people find each other, but they are essentially a competitive space with a lot of different options. Many people make the mistake of acting too cool and laidback, mirroring traditional dating strategies. However, dating apps are a place where sincere, consistent effort is rewarded.

This doesn’t mean you should act desperate but rather that you should put real thought into the interesting questions you ask. These questions should make a strong first impression, differentiate you from other dating opportunities, and give some indication of what kind of person you are.

Try not to overthink your questions either. The great thing about an interesting dating app question is that it can be more openly comedic, outlandish or random than questions in regular conversations. It’s the ideal opportunity to put your unique qualities on display.

Here are some examples that you can use in your opening message, during text chat or as a way to save face and continue the conversation if they didn’t respond to your last message.

1. What’s the most unexpected thing you’ve learned about yourself recently?
2. If you could choose one fictional character to be your wingman, who would it be?
3. What’s your go-to comfort show when you need a mood boost?
4. What’s the most fun or unusual date idea you’ve ever thought of?
5. What’s something you think everyone should try at least once?
6. If your dating app bio could talk, what would it say about you?
7. What’s a random passion that makes you unique?
8. What’s your favorite way to spend a Sunday afternoon?
9. What’s the best icebreaker question someone has ever asked you?
10. What’s something you’d love to experience with the right person?

You can immediately tell if you’ve asked an interesting question by the response you get. If it’s effusive and enthusiastic, you’ve succeeded. If the response isn’t very long or feels largely indifferent, you haven’t.

But if you’re wondering if there’s a way to guarantee that the question you’re asking will be interpreted as cool and interesting by the other person, unfortunately, there isn’t. There are ways to hedge your bets, though. A recent joint study by Harvard and Imperial College Business School proposed that a Conversational Circumplex exists in all interactions, where conversational success relies upon three basic factors: knowing what you want from the conversation, predicting what the other person wants and using behavior and topics that balance the divide between these two motivations.⁶

In this sense, a successful question is inherently an interesting one. So, it’s more about establishing your goals before you socially approach someone, using contextual and implicit cues in how they react to you to figure out how they want the interaction to go and feeling confident enough in yourself to pivot your approach on the fly when a question doesn’t get the response you expected. 

How to ask interesting questions?

As we mentioned, different people find different things interesting. Here’s how you can adapt your approach depending on who you’re interacting with.

• Be purposeful in your questions. Ask yourself first what you hope this question will achieve.
• Avoid close-ended questions that only have a limited range of answers.
• Use what you already know about them, their dating profile or clues in their appearance to understand them better and shape your questions around that.
• If you want to go deeper with a question, sharing something personal about yourself first is a great way to inspire reciprocity.
• If you get a promising response, always ask follow-up questions to express further interest and attention.
• Remember that active listening is the key to asking genuinely interesting questions that build on your existing connection.
• Timing is probably one of the most important factors. A poorly timed question can interrupt the flow of a good conversation, come across as awkward or simply kill the mood. There is a natural space for interesting questions in a conversation and with practice, recognizing those moments will become second nature. 

What are the do’s and don’ts of asking interesting questions?

Here are some good tips to follow when you’re coming up with interesting questions to ask, along with some things to strongly avoid.

• Do ask questions that begin with ‘how’ and ‘what’ instead of ‘why’. This small grammatical difference can dramatically change the tone of a question.  
• Do express genuine interest and curiosity in them by using their responses to inform later questions.
• Do start small and work your way up to more personal or intimate questions as the conversation develops.

• Don’t ask leading or close-ended questions or even the most interesting questions will feel inauthentic.
• Don’t allow your attention to wander off from them toward your phone or your surroundings while they answer. Stay completely locked in during an interaction. 
• Don’t ask too many questions in a row or more than one question at a time.

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