269 Random Questions to Ask To Ask Your Date

A random question is something a little zany and unexpected. We use different random questions to ask people in a conversation to intentionally veer wildly off-topic and disrupt the current exchange in a pleasant, mentally stimulating way that can cause it to change course and head towards interesting, unpredictable directions.

Regardless of whether you’re looking for the most random questions to ask someone or simply something a bit surprising to get people thinking, the most important factor is timing. Random questions can be conversation killers in an already bubbly exchange. It’s more ideal to explore them as potential conversation starters, to reinvigorate the energy of a waning one or gently pivot from topics that could be considered sensitive or detract from the positive atmosphere.

Random questions are designed to be fun and compelling, adding natural spontaneity to your interaction and creating a more inviting, less inhibited space. They also express a playful curiosity in the other person that inherently runs a little deeper, making you seem more versatile and creative while often encouraging them to reciprocate.  

There are different forms of random questions you can try, depending on the type of relationship you have with the person and the desired effect. Serious and thought-provoking questions help people be more vulnerable and open, while silly and open-ended random questions are better when you want to change the general mood of the conversation.

Let’s explore some unexpected questions you can send as a funny text, use on a dateor even a random question of the day game to play with your crush as you get to know them better.

Random questions to start a conversation

These are ideal if you’re stuck on what to send as an opening text or you want to ease any nerves in an exchange that feels uneasy. Random conversation starters tend to break the ice in an intriguing way, often sidestepping perfunctory small talk and basic information exchange, diving straight into the meat of the conversation.

These conversation starters are often more unique and engaging, making them a great way to break out of old conversation habits. Whether it’s with your partner or someone new you want to impress, like on a first date. We’d suggest using them sparingly and purposefully, only really exploring unexpected conversation prompts and different random questions to ask to shake things up and create a different energy. You don’t want every conversation to feel like a mystery door game. Conventional social scripts can be a bit samey but they’re comfortable and reliable, which is also important.     

Here are a few to get you started:

1. What’s a small thing that always makes you smile?
2. If you could have any scent as a candle, what would you choose?
3. What was the last photo you took on your phone?
4. What’s a skill you wish you could learn instantly?
5. If you had to describe your current mood as a type of weather, what would it be?
6. If you could swap lives with someone for a week, who would it be?
7. What’s the most unusual thing you’ve ever eaten and actually liked?
8. If you had to pick a theme song for your life, what would it be?
9. What’s a random hobby you’d love to master?
10. Do you prefer sunrises or sunsets?
11. What’s the most spontaneous thing you’ve done recently?
12. If you had to live in another country for a year, where would you go?
13. What’s the best compliment you’ve ever received?
14. If you could time travel for one day, where would you go?
15. What’s the strangest coincidence that’s ever happened to you?

Good random questions

You may be wondering how we’d define a “good” question. We’d say a good random question is the one that creates the most value in a conversation and can also be posed in any interaction, regardless of your relationship and conversational tone. For this reason, they tend to be a little less quirky and playful, instead focusing on exploring the other person’s life and passions, using the power of the unexpected to get more authentic answers.  These kinds of random questions lead to unexpected conversations, which have been scientifically shown to be more engaging, mentally stimulating and memorable on a neurological level.¹ A good one is also able to get past people’s defenses by seeming random while subtly touching on people’s values, what’s most important to them and the things they fill their existence with. 

You can use these questions more openly and frequently, as they’re generally more unexpected than odd or abstract. Their goal is simply to express curiosity and try to understand what memories and passions drive them, which they’ll reflexively appreciate.

Here are a few ideas you could try that we consider good:

1. What’s something you’ve been proud of recently?
2. If you could listen to only one album for a month, what would it be?
3. What’s a simple pleasure you never get tired of?
4. What’s a book or movie that genuinely changed your perspective on something?
5. Who is someone you admire, and why?
6. What’s something you do that instantly makes you feel better?
7. If you could relive one year of your life, which would it be?
8. What’s a smell that instantly takes you back to childhood?
9. What’s a totally useless skill you’re proud of?
10. What’s the kindest thing a stranger has done for you?
11. If you had to describe yourself in three emojis, which ones?
12. What’s a fear you’ve overcome?
13. What’s a book or movie that changed your perspective on life?
14. If you could create a holiday, what would it celebrate?
15. What’s a guilty pleasure TV show you secretly love?

Random questions to ask someone to get to know them

Random get to know you questions aim to achieve something similar to the typical questions one asks during small talk but in a different, more original way. One that compels them to think about their response instead of defaulting to some stock answer.   

By finding the right questions to ask, you can take the conversation to a deeper place – often exploring the more guarded aspects of their personality and the things that make them tick. But in a way that seems engaging and playful rather than nosy or intrusive. 

It’s best to mix these random questions to get to know someone with more conventional questions in that area, like the ever-reliable “What are your hobbies and interests?” Remember that you’re using these questions as an unconventional bonding tool by evoking interesting responses, not to simply create a random conversation.

Get the process started on the right foot with these:

1. What’s something you’re unapologetically nerdy about?
2. How do you like to spend a rainy day?
3. What’s a deal-breaker for you in a friendship?
4. If you could witness any event in history, what would it be?
5. What’s a piece of advice that has always stuck with you?
6. What’s something you’re curious about learning right now?
7. What’s your idea of a cozy evening?
8. What’s a goal you’re working toward this year?
9. If you could meet your younger self, what advice would you give?
10. What’s one thing that always makes you laugh?
11. Do you enjoy meeting new people, or do you prefer familiar faces?
12. What’s a memory you often think about?
13. What motivates you on tough days?
14. If you could live anywhere for a year, where would it be?
15. What’s a dream you’ve never shared out loud?

Random questions to ask a guy

Random questions are generally equally effective on either gender, provoking similar responses. Where you could vary the kinds of questions to ask a guy by basing them on what you already know about him or by asking about more classically masculine topics.

Studies have shown that guys tend to be less open in conversations, particularly when it comes to sharing anything they perceive as negative.² So random questions are great for facilitating sincere -bonding. They’re also effective to get someone to be more vulnerable and open by being less direct and more playful with the questions.

Try to remember that you want to explore the person’s values and interests, not define them by it, so only ask a few. The best kind of random question to ask a guy should inspire them to be more curious about you and respond with similar questions.

Let’s look at some examples of what you could ask him:

1. What’s a skill your father or a father-figure taught you?
2. If you were to build a cabin in the woods, what’s the one luxury item you’d bring?
3. What’s the most challenging thing you’ve ever built or fixed with your own hands?
4. What’s a “guy movie” that you think is overrated?
5. What’s something you think every man should know how to do?
6. What’s your go-to comfort meal when you’ve had a rough day?
7. If you could compete in any extreme sport, what would it be?
8. What’s the funniest prank you’ve pulled on a friend?
9. What’s a movie you can quote start to finish?
10. What’s your favorite way to spend a Sunday morning?
11. If you had to grow a crazy mustache style, what would you pick?
12. What’s a random skill you have that nobody expects?
13. Would you rather build something with your hands or solve a puzzle?
14. What’s the most adventurous thing you’d love to try?
15. If you could live in any decade, which one would you pick?

Random questions to ask a girl

As with men, the kind of random questions to ask a girl isn’t generally that different. A person’s age, background and frame of reference have a more profound impact on the kinds of questions and topics that would engage them than gender.

But by asking random questions that can often relate to their interests orexperiences within society, you can show you’re more sensitive and open to perspectives that diverge from yours without changing the mood of the conversation by being too serious and direct. This is why questions are so useful in social settings, because you are not only getting to know someone, you’re offering a deeper gesture of understanding and emotional investment in the act of asking.

Showing that you’re playful yet sensitive can be really helpful when dating. We’d advise starting with broad questions that could speak to someone’s experiences and see what kind of energy their response has.

We’ve put together a few examples you could try on a woman:

1. What’s a character in a book or movie you strongly relate to?
2. If you could have a dinner party with any three people (living or dead), who would you invite?
3. What’s an accomplishment you’re proud of but don’t get to talk about often?
4. What’s a simple act of kindness that someone once did for you that you’ll never forget?
5. What’s a compliment you wish you received more often?
6. What’s a song that always puts you in a good mood?
7. If you could design your dream room, what would it look like?
8. What’s a small ritual you love doing just for yourself?
9. Which fictional character do you relate to most?
10. What’s a silly superstition you secretly believe?
11. If you could instantly change your hairstyle, what would you try?
12. What’s the last thing that made you laugh until you cried?
13. What’s your favorite type of weather and why?
14. If you could star in any movie genre, what would it be?
15. What’s a random snack combo you swear by?

Random questions to ask your partner

These are the kind of unexpected questions that work well in a group or a one-on-one setting with friends, putting a fun, silly spin on the conversation.

Whether it’s deepening the connection you have with your existing partner or trying to forge a bond with a new person in your life, finding some good random questions to ask them when you interact can improve how you communicate and create a greater sense of togetherness.

We can get stuck in certain routines with our partners, often taking their place in our lives for granted. By asking random questions like these examples every once in a while, it also expresses that your relationship is still evolving, shows appreciation for the impact they’ve had on your life and that you’re there for them, regardless of whatever random thing they may want to talk about.

1. What’s a memory of our relationship that you think about when you’re feeling down?
2. If our relationship was a TV show, what would its theme song be?
3. What’s a trip you think we should take together?
4. What’s an inside joke we have that makes no sense to anyone else?
5. If you could give me an award, what would it be for?
6. What’s the weirdest inside joke we’ve ever created?
7. If our group had a theme song, what would it be?
8. What’s the most epic trip we could plan together?
9. What’s a trend we should never have followed?
10. Who in our relationship would survive longest in a zombie apocalypse?
11. What’s your favorite story about us that you always retell?
12. If we were in a band, what role would you have?
13. What’s a crazy challenge we should try together?
14. Who’s the most likely to become famous?
15. What’s something we should add to our bucket list as friends?

These kinds of questions are designed to pique the interest of the people you like and distinguish you from people they’ve dated in the past. Coming up with unique and random questions to ask your crush also shows that you’re creative and inventive, which studies have found is an important factor in how people assess potential partners.³

It also helps you test compatibility, gauge their feelings for you in more subtle and abstract ways and create the right kind of bond with someone you like. As you’re getting to know each other, you’re also establishing your overall dynamic and the different ways you relate to each other.

Making some of these questions random not only leads to surprising discoveries in each other’s personalities and life stories, but it also makes your communication style more versatile. It tells your crush that they can be vulnerable around you and freely share whatever’s on their mind.

Here are some handy instances to help get you on the right track:

1. What’s your go-to comfort movie or TV show?
2. What’s a song that can instantly get you to dance?
3. If we were to go on an adventure, what kind would it be?
4. What’s a little, everyday thing that makes you happy?
5. What’s the best compliment you’ve ever received?
6. What’s a subtle way someone can win your heart?
7. Do you think chemistry happens instantly or grows over time?
8. What’s your idea of an unforgettable date?
9. What’s a song you’d add to a romantic playlist?
10. Do you like thoughtful surprises or adventurous ones?
11. What’s the cutest thing a partner has done for you?
12. What’s a memory you’d love to recreate with someone special?
13. Do you believe in soulmates?
14. What’s a tiny gesture that makes you feel cared for?
15. Would you rather have a weekend getaway or a stay-at-home date?

Random silly questions

It’s hard to have randomness without silliness and whimsy coming along for the ride. So, embrace random humor and how it can bring a light tone to your daily interactions with your date or partner. 

By coming up with an outside-the-box, random fun question to ask, you’re both amusing them in the act of asking the question and opening the conversation to various humorous and often tangential topics. It essentially creates the perfect vibe for you to be more kind and forthright with each other.

We suggest using all types of random questions in limited measure, so that it doesn’t seem gimmicky or give a disjointed feel to the conversation. But funny random questions tend to be the easiest to introduce semi-regularly in conversation because people naturally find humor disarming and performative.      

If you’re stuck on which silly random questions you should ask, try building on one of these:   

1. What’s the most ridiculous thing on your bucket list?
2. If you had to communicate using only emojis for 24 hours, which 5 would you choose?
3. What would be the title of your celebrity gossip magazine cover story?
4. If you were a ghost, who would you haunt and how?
5. What’s a weird food combination you secretly enjoy?
6. If you had to wear one Halloween costume forever, what would it be?
7. Would you rather hiccup every time you laughed or sneeze every time you smiled?
8. What’s the weirdest nickname you’ve ever had?
9. If you had to pick a cartoon voice for yourself, which one?
10. Would you rather live in a house made of candy or one made of LEGO bricks?
11. What’s the dumbest dare you’ve ever done?
12. If you had to rename yourself after a fruit, which one?
13. Would you rather always talk in rhymes or only whisper?
14. What’s the weirdest dream you remember?
15. If you were invisible for a day, what’s the first thing you’d do?

Random serious questions

Random serious questions leave humor at the door, instead focusing on revealing the deeper aspects of the person you’re talking to but in a more subtle and compelling way. These questions explore concepts like their value system, philosophical outlook on life and where they feel like they’re headed as a person.

Finding the right deep questions to ask at the right time shows your partner you really hear them when they talk and that you have an unconventional yet refreshing approach to tackling some of life’s grander issues. It’s also an affable, less intense way to show them that you’re interested in growing closer. 

These kinds of questions are best used when you’re just starting to build your bond with somebody or someone who’s more socially reserved in conversation. As you grow closer and build rapport, the random serious questions you ask will start to become more direct and, hopefully, reciprocated.

Here are some good example questions that don’t require much vulnerability from the person you’re asking.  

1. What does the word “home” mean to you, beyond a physical place?
2. Do you think a person can fundamentally change?
3. What’s a belief you held strongly a few years ago that you no longer do?
4. What is a legacy you hope to leave behind?
5. How do you define success for yourself?
6. What’s a decision that completely changed your life?
7. Do you think happiness is permanent or fleeting?
8. What’s the hardest lesson you’ve learned so far?
9. Do you think people are naturally good or bad?
10. What motivates you to keep going when things get tough?
11. What’s one value you refuse to compromise on?
12. Do you believe in destiny or free will?
13. What’s the best advice you’ve ever been given?
14. What role does kindness play in your life?
15. What do you want your legacy to be?

Random thought-provoking questions

Thought provoking questions are puzzles, hypotheticals and brain teasers designed to force someone to fully engage with what you’re saying and be creative in their response. These answers can help you understand someone better, revealing how they intellectually approach unusual ideas and their attitude towards being pushed slightly out of their comfort zone in a conversation. Asking random thought-provoking questions iallows your date or partner to discover more about their own values. These questions are often unique, demanding not just attention to the conversation but a vested desire to continue along this path. While different people seek novelty to different degrees, studies suggest it may be an innate part of our evolutionary drive, predating even humankind.⁴

Use these questions when you’re experiencing a sudden lull in conversation or to gently steer into deeper waters with a query that’s more intellectual than personal.

We’ve put together a few you could try:

1. If you could know the absolute and total truth to one question, what question would you ask?
2. Is it better to be a small part of something big, or a big part of something small?
3. What is something that is morally acceptable now but probably won’t be in 100 years?
4. If your memories were stored in a library, what would be the title of your most-visited book?
5. Does technology bring people closer together or drive them further apart?
6. If you could know the answer to one mystery, what would it be?
7. Do you think time is something we create or something that exists?
8. What’s a question you wish people asked you more often?
9.  What do you want your legacy to be?
10. What’s the meaning of home to you?
11. Would you rather live for 200 years or relive your life twice?
12. Do you think humans are progressing or regressing as a society?
13. What’s something you think we take for granted?
14. Do you believe dreams have hidden meanings?
15. What’s one thing you’d change about the world right now?

Random this or that questions

This or that questions are binary, having only two possible answers, which are provided. They can be about any topic, such as people’s taste in certain foods, their deeper perspectives or even introduce a whimsical yet simple hypothetical into an exchange. This makes them ideal for group interactions as well.

While these questions are closed-ended, which can sometimes harm the pace of a conversation, the answers act as a quick guide of where to take the conversation next. They provide launch points for better interactions. For instance: “tropical vacation or cultural city vacation?” The answer will quickly tell you how they approach leisure time, giving you inspiration for the kinds of random questions to ask that would speak to their character and lifestyle.

These questions are supposed to be quick-fire, encouraging a more vibrant back-and-forth, which makes them perfect for text conversations and dating apps, where blocks of text can be intimidating. In this format, you often want to spark their interest to keep them engaged and texting back.   

1. City life or country life?
2. Spontaneous adventure or meticulously planned trip?
3. Sweet or savory snacks?
4. Call or text?
5. Unlimited money or unlimited time?
6. Rainy day at home or sunny day outside?
7. Board games or video games?
8. Chocolate cake or apple pie?
9. Podcasts or audiobooks?
10. Sneakers or sandals?
11. Camping in nature or staying in a cabin?
12. Dancing or singing?
13. Comedy shows or documentaries?
14. Reading a book or writing a story?
15. Cold drinks or hot drinks?

Random open-ended questions

Conversely, open-ended questions encourage longer, more descriptive answers. They creatively investigate how the other person organizes their life, what’s most important to them and their dreams. Or they could simply ask them to describe the preparation method for their favorite smoothie. The goal is just to get them talking, so they grow more comfortable and self-assured in the conversation, perhaps even coming up with random questions to ask of their own.    

But sometimes, even open-ended questions can elicit very basic responses if the person is feeling shy or a bit closed off. Making your open-ended questions more random often adds an interesting or amusing spin to the question, which can come across less like an inquiry than an invitation for being vulnerable and more active in the conversation. 

Most of the questions we’ve included as examples are open-ended. These are generally appropriate at any level of intimacy, regardless of the conversational tone, depending on how personal they are.

Here are some general questions you can ask:

1. Describe a perfect day for you, from start to finish.
2. What is a skill you’ve always wanted to master,and what’s holding you back?
3. Tell me about a time you felt completely out of your comfort zone.
4. What would you do if you had an extra hour in your day?
5. How would you describe your sense of humor?
6. What’s a project you’ve been dreaming of starting?
7. What’s a childhood dream you still think about sometimes?
8. What’s one moment that shaped who you are today?
9. What’s a habit you’d like to build this year?
10. What do you hope people remember about you?
11. What’s a challenge you’re working on overcoming?
12. What’s one thing you want to experience in the next year?
13. What’s a small act of kindness you’ve witnessed that stayed with you?
14. What’s a lesson life taught you recently?
15. What’s your personal definition of success?

Random intriguing questions

Intriguing questions are a healthy balance between deep and thought provoking – but in a way that doesn’t challenge the person. Finding random intriguing questions will often form the filler during interactions, occupying the space between more intimate or novel questions and topics. This is often how a conversation graduates from small talk.

An interesting question to ask is about sparking curiosity, establishing a more active communication style with people in your life, introducing engaging ideas into the conversation to make it more energetic or expressing an interest in the other person’s deeper perspective on things. It’s not simply about the question being interesting but about its larger implications, opening up new pathways in the conversation.

These are handy questions to introduce once the getting to know you phase is coming to a close and you want to see if you click on a more personal level. Start out with one of these to get the process going. 

1. What’s the most interesting documentary you’ve ever watched?
2. What’s a “fact” you learned that later turned out to be untrue?
3. If you could have a conversation with any animal, which would you choose and why?
4. What’s an obsolete piece of technology you miss?
5. What’s the most interesting thing you’ve read or learned this week?
6. If you could have dinner with any historical figure, who would it be?
7. What’s a random fact about the world that fascinates you?
8. Do you believe in alternate realities?
9. What’s the most intriguing tradition you’ve heard of?
10. If you could unlock one mystery of the universe, what would it be?
11. What’s a movie or book ending you’d rewrite?
12. Do you think people show their true selves under pressure?
13. What’s something you wish you understood better?
14. Do you believe art changes the way we think?
15. What’s a thought that keeps you curious?

Random questions about life

These questions hone in on the person you’re talking to, opening up questions about their life story, inner thoughts and hopes for the future. This is often our default mode when we’re talking. A study published in the PNAS journal found that we spend 30-40% of our total time talking telling others about our subjective experiences. It’s such a big part of our social model that our brains chemically reward us when we disclose information about ourselves.⁵

So, the mechanics are in place, but how do you make your interaction stand out from everyday conversation? Well, by asking more outside-the-box and random life questions instead of the generic ones we typically get in conversation, like “What’s your favorite memory?”

Because people are so comfortable with the topic, you can often pose these questions at any point during an interaction, whether it’s to pivot to more interesting topics or just find out a piece of information about the person that you’re curious about.

If you’re unsure of how to structure these questions, here are some handy examples: 

1. What’s a lesson that took you a long time to learn?
2. What period of your life do you feel most nostalgic for?
3. What do you wish you had more courage for?
4. If you could give your younger self one piece of advice, what would it be?
5. What’s something you want to be remembered for?
6. What’s a small thing that makes everyday life better for you?
7. Do you think happiness is something we chase or create?
8.  What’s a philosophy you try to live by?
9. What’s the most surprising lesson life has taught you?
10. Do you believe balance is achievable in life?
11. What’s a habit that helps you stay grounded?
12. What’s one thing you’d like to do more often in your daily routine?
13. What do you think makes life meaningful?
14. What’s a risk you took that paid off?
15. What’s something you hope to accomplish in the next five years?

Asking the right questions becomes particularly important in a romantic setting, like on first dates. Courtship puts you in a unique social setting where you’re connecting with someone new, motivated to make a good impression, but also aiming to appear at ease and self-assured.

Luckily, this isn’t a social tightrope you have to balance on but a core motivating factor that pushes these interactions forward. Romantic interest is essentially social jet fuel, in this way. And by finding just the right random first date questions, you can add velocity and automatically create a more fun, intriguing and compelling atmosphere that lets even fledgling connections blossom. 

You can use first date questions early on as you try to find common ground and interesting new topics to discuss. They’re also helpful when you want to recover from those natural lulls in conversation that happen on first dates.

If you’re looking for inspiration, use these as your baseline for appropriate questions:

1. What’s a tradition from your family that you’d like to continue?
2. What’s something you’re really passionate about that might surprise me?
3. What does an ideal weekend look like for you?
4. What’s a travel destination that’s at the top of your list?
5. What’s a small, kind gesture that means a lot to you?
6. What’s the quirkiest thing about you?
7. Do you prefer city life or countryside escapes?
8. What’s a small detail that makes a date unforgettable for you?
9. What’s a movie you can watch over and over?
10. What’s a random food you could eat every day?
11. Do you enjoy late-night talks or early morning walks?
12. What’s a place in the city you’ve always wanted to try?
13. Do you believe in signs or coincidences?
14. What’s the funniest first date story you’ve heard?
15. What’s one thing you think makes a great first impression?

Random questions to ask on a second date

During the second date, you’ll likely have gotten past most of the nervous small talk and getting to know you questions and move on to more engaging ones. A second date means that there is at least some initial chemistry, so try to think of some random second date questions that are a little more personal, expressing a growing understanding and appreciation for the other person.

While first dates are about chemistry, second dates are about building rapport and establishing deeper aspects of compatibility, like personality and communication style. On second dates, the importance of content in questions often takes a backseat to how questions can help create a more intimate and entertaining conversation and add a specific energy to your interactions.

Use one of these examples whenever the opportunity presents itself or steer the conversation away from small talk.    

1. What’s the strangest thing you believed when you were a child?
2. Do you have any weird dating rules that you follow?
3. How many times a day do you think about the Roman Empire?
4. What’s something that makes you cringe but isn’t objectively that bad?
5. What celebrities have you been told you look like?
6. What’s something you’ve always wanted to try with a partner?
7. What’s the most spontaneous adventure you’ve been on?
8. Do you prefer cooking a meal together or dining out?
9. What’s a personal passion you’d love to share?
10. What’s the most fun trip you’ve taken?
11. Do you believe second dates are more relaxed than first dates?
12. What’s a hidden talent you’d be willing to share?
13. What’s a goal you’re currently working on?
14. What’s a hobby you’d introduce to a partner?
15. Do you think laughter is the key to a great date?

Random questions to ask on a dating app

Conversations on dating apps tend to work quite differently from other kinds of exchanges. Not only are they quite purposeful, but they can also end abruptly for no particularly apparent reason. Having a decent collection of random dating app questions that you use to break the ice and get past that uneasy introductory period can help you stand out amongst other singles online.  

The key aspect here is to ask something unique and directly engaging, or your message may end up looking like every other opening message in their inbox. You don’t have to make it some high-concept joke or profoundly insightful question. Simply try taking the question you’d normally ask and putting an unexpected twist on it or just a simple question, but about something they wouldn’t ordinarily think about.

The best time to use these questions is during the early stages of your conversation, if their responses start to become lackluster or monotonous, or when you’re getting back in touch after taking a break from messaging each other.

Here are a few tried and tested random questions to ask on a dating app:

1. Based on my profile, what’s a movie you think I’d like?
2. What’s the most spontaneous thing you’ve ever done?
3. Describe your perfect sandwich. I need to know the details.
4. What’s a popular opinion you strongly disagree with?
5. If you had to pick a theme song for your life right now, what would it be?
6. What’s the funniest profile you’ve ever seen on here?
7. Do you prefer long chats before meeting or jumping right into a date?
8. What’s your go-to conversation starter on dating apps?
9. What’s something in your profile that always gets comments?
10. What’s the most fun first date idea you’ve had?
11. If you could design the perfect app date, what would it be?
12. What’s the weirdest message you’ve ever received?
13. Do you prefer voice notes, texts, or video calls on apps?
14. What’s one thing you wish people asked more on dating apps?
15. What’s the best success story you’ve heard from dating apps?

What is a random question?

A random question is any kind of question that is unexpected or considered outside of people’s typical social scripts. Randomness encompasses so many scientific and philosophical concepts, but one consistent theme identified by studies is uncertainty and unpredictability.⁶

Randomness touches on an odd paradox in human beings. A study in the Psychological Science journal found that people instinctively avoid randomness because it represents the unknown and, therefore, possible danger. Conversely, they also found that people enjoy unexpected outcomes more than expected outcomes when that outcome is pleasant.⁷

The thing is we find breaking our routine very stimulating but we’re also naturally afraid of things outside our comfort zone. This is why random questions are a pleasant way to introduce the unexpected to the dynamic. Questions are low-stakes and create a more exciting exchange without adding more uncertainty to a conversation. Just remember not to preface it with, “Can I ask you a random question?”  

What are the most random things to talk about?

Random questions can often take the conversation to unexpected places, but not all of the destinations will necessarily be random. If you want to have a full-on random conversation with someone you already know quite well (and who enjoys randomness), try out one of these random things to talk about.

• Would you rather – Make up two crazy, contrasting scenarios and ask the other person to pick between them. These are often more amusing if both options are unpleasant, but you have to work through which one is the least unpleasant.  
• Strange food combos – Everybody has their own version of complementary foods (for instance, French fries and ice cream). Sharing them can be a funny exchange and you may unearth some truly ingenious suggestions.
• Bad dates – This can be a particularly bold and amusing topic with someone you’re on a date with. It will give you a better idea of their dating style and let you bond over the lighter ups and downs of your single life.
• Random stories – Human beings really connect with storytelling in conversation. We tend to be narratively minded. Adding randomness as a qualifier is a great way to add humor and a touch of the unexpected to your interaction.  

How to use random questions effectively?

Asking random questions can open up surprising and fun conversations — if you use them the right way. Here are a few tips to make them work for you.

• Try to find common ground early on. The random questions you ask can be more effective if you have a general topical area to aim for. One that can produce a fruitful conversation for both of you.
• Don’t overthink questions. Be bold and ask them. They don’t have to be perfect, they just need to spark a dialogue.
• Use random questions sparingly in conversations. Think of it as a spice to generally enrich the conversation rather than one of the principal ingredients.
• Don’t ask random questions if the conversation is flowing and seems to have a clear purpose. You may end up interrupting the connection you were already making.
• As it’s already random, try to keep the question short and simple or you may end up confusing them.
• Use random questions to express authentic curiosity and interest – ultimately leading to a warmer conversation – not to test or force a joke onto the person you’re talking to.

When is the best time to ask random questions?

When there’s a lull in conversation that is quickly becoming a strained silence or when you’re stuck in a certain conversational track that isn’t engaging for either of you. It’s often useful during transitional periods of the relationship as you go from strangers to acquaintances to friends to close friends, or as a way to kickstart the process of evolving the relationship itself.

Timing often isn’t as important as frequency. As we showed, people have a natural apprehension of randomness. If you keep on drawing from your collection of random questions to ask instead of using them sporadically to keep things fresh, the conversation won’t have a playful, random dynamic; it will be a random conversation. That’s too much chaos and uncertainty for a normal person to find rewarding.

Try to remember that you’re using randomness as a tool to express that you’re a creative and engaging thinker who brings a vibrant, unique energy to interactions. It should never be the centerpiece of your conversations with a date or your partner.