By January Nelson Updated December 3, 2020

Awkward silence during small talk is never fun. When a conversation fizzles, you need to ask the right questions to your conversation partner. Whether you’re talking to an old friend or a new person you’ve just met, a good question has the potential to make a conversation last for hours on end.

In order to make you come across as more interesting in any conversation, you should ask an open question that will help you get to know a person better. To help you on your journey, here is a big list of questions to ask to get to know someone:

Jump to: Questions about Likes • Interests • Fun • Family • Love • Values • Aspirations • Deep • Philosophical • Religion • Life • Career

Likes

Simple conversation starters about their likes and dislikes:

What is your favorite food?
What is your favorite book?
What is your favorite color?
What is your favorite movie?
What is your favorite thing about summer?
What is your favorite thing about winter?
What is your favorite song to blast in the car?
What is your favorite holiday to celebrate with your family?
What is your favorite memory from your childhood?
Where is your favorite place to vacation?
What was your favorite subject in school?
What is your favorite letter of the alphabet?
What is your favorite podcast to listen to on long drives?
What is your favorite quote from a movie, novel, or show?
What is your favorite number?
What is your favorite candy to eat at the movie theater?
Where is your favorite restaurant to take dates?
What is your favorite homemade meal that your mother cooks?
What is your favorite breakfast cereal?
What was your favorite toy when you were a little kid?
What is your favorite flavor of coffee?
What is your favorite television show of all time?
What is your favorite boy band?
What was your favorite cartoon when you were younger?
What is your favorite state you’ve visited?
What is your favorite ride at an amusement park?
What is your favorite season?
What is your favorite type of flower?
What is your favorite board game?
What was your favorite book when you were little?
Who is your favorite superhero?
Who is your favorite actor or actress?
Who is your favorite athlete?
Where is your favorite place to shop for clothing?
What is your favorite candle scent?
What is your favorite day of the week?
What is your favorite website?
What is your favorite type of car?
What is your favorite ice cream flavor?
What is your favorite way to relax at the end of a long day?

Interests

Icebreaker questions about their interests:

What is your guilty pleasure?
What do you do for fun on weekends?
What is your favorite form of social media: Twitter or Instagram or TikTok?
Who is your favorite comedian to watch when you need a laugh?
What’s your favorite sport to play with friends?
What’s your favorite video game to play with friends?
What’s your favorite drinking game to play with friends?
Do you do any volunteer work? Do you donate to any charities?
Who is your closest friend–and what do you like to do together?
What is your favorite type of craft to work on? Painting or writing or knitting or something else entirely?
What show can you watch over and over again without getting bored?
Do you play any musical instruments?
Do you know any other languages?
What genre of books do you usually read in your free time?
What is your favorite form of exercise? Biking or swimming or weightlifting or power walking?
Do you know how to dance? What songs make you want to get up and move?
What hobbies did you have when you were younger that you gave up?
What hobbies did you pick up when you were younger that you still enjoy?
Do you prefer solo hobbies or hobbies that involve big group activities?
Do you enjoy cooking or baking? What’s the most delicious thing you can make?
Do you garden? If so, what types of seeds have you planted?
Do you enjoy hiking? If so, what was the best trail you’ve ever hiked?
Are you a skilled artist? What’s the most impressive thing you’ve ever drawn?
Have you ever gone camping? Do you have any fun stories about the wilderness?
Are you a dog person or a cat person?
What is your favorite conversation topic?
Do you collect anything? Rocks or stamps or Pokemon cards?

Fun

Examples of a fun question to spark conversation:

What’s the weirdest thing you believed as a child?
What would be the title of your memoir?
At a party, where can someone usually find you?
What is the funniest name you’ve heard someone call a pet?
If a movie was made of your life, what actor would play you?
If you could have an exotic animal as a pet, what would it be?
Have you ever social media stalked someone?
What is your go-to pose when taking a selfie?
What is your favorite celebrity scandal?
Did you have an imaginary friend when you were little?
What are your favorite three topics to talk about?
What’s your earliest memory?
If there were 26 hours in a day, what would you do more of?
What’s the longest you’ve gone without sleep (and why)?
Aside from necessities, what one thing could you not go a day without?

Examples of a random question that will break the ice:

If you were forced to get a tattoo today, what would you get?
What is your secret, hidden talent?
What’s the last television show you binge-watched online?
How many pets do you have? What are their names?
Do you eat the crusts on your sandwiches?
Who is your hero? Is it a celebrity or someone you know in real life?
How long can you go without checking your phone?
Do you believe in psychics? Have you ever visited one?
If your friends created a band, what would it be called?
What’s your favorite pizza topping? What about ice cream topping?
Do you believe parallel universes exist?
Do you believe aliens exist?
Have you ever seen a ghost in real life?
Do you prefer horror movies or romantic comedies?
What movie ending do you wish you could change?

Examples of a funny question they can answer:

What is the weirdest conversation you’ve ever overheard?
What’s the most ridiculous fact you know?
What is something that everyone looks stupid doing?
If animals could talk, which would be the rudest?
What’s the most imaginative insult you can come up with?
What would be the absolute worst name you could give your child?
If life were a video game, what would some of the cheat codes be?
What would be the coolest animal to scale up to the size of a horse?
What set of items could you buy that would make the cashier the most uncomfortable?
Who do you know that really reminds you of a character in a TV show or movie?
What is something that is really popular now, but in 5 years everyone will look back on and be embarrassed by?
Are you the type of person who folds toilet paper over or under?

Examples of a fun hypothetical question for them to answer:

What would be your strategy for a zombie apocalypse?
What two animals would you like to switch the sounds they make?
What cartoon world do you wish you could live in for a week?
If you could put wings on any species of animal, what animal would you choose?
If you could go back in time and give your parents advice before you were born, what advice would you give them?
If you were required by law to get a full body tattoo, what would you get tattooed over your entire body?
If you could erase one thing from existence, even the memory of the thing, what would it be?
If you were reincarnated as an animal based on your personality, what animal do you think you would come back as?
If you had to get a tail, what tail would you want and what would you use it for?
If your dog or cat suddenly spoke one sentence and then never spoke again, what would be the most unsettling sentence they could say?
If you could go back and hands down win any argument you’ve had with anyone, what argument would you choose to win?
If you had to be haunted by a ghost for the rest of your life but could choose which dead person the ghost would be, who would you choose as your ghost?
If you had an animal or plant renamed in your honor, what would you want to carry your name?
If you could choose any job to be replaced by robots, what job would you make obsolete?
What movie-worthy heist would you pull if you knew, in the end, you would get away with it?
If you were given any one luxury item, but you couldn’t sell it, what luxury item would you want?
If you were the next pied piper, what animal would you want to be able to compel to follow you?
If you were a fashion icon and whatever you wore would become a fashion trend, what fashion trends would you start?
If you were chosen to be the first human to make contact with aliens, would you want to?
You get one text, no more than 160 characters, that gets sent to everyone’s phone. What does it say?
If you died and had to choose one place to haunt for the rest of eternity, where would you choose to haunt?
What amusement park do you wish existed?
If you could change what people say after someone sneezes, what would be the funniest thing for people to say?
If you could bring back any canceled TV series, which TV show would you choose to bring back?
If all animals became as intelligent as humans and were miraculously able to speak, what jobs would be well suited to which animals?

Examples of a rhetorical question that doesn’t require an answer:

Are you kidding me?
Does a bear poop in the woods?
Is rain wet?
Is the pope Catholic?
Is hell hot?
What’s the point?
What’s the matter with kids today?
Who cares?
Why me?
Does it look like I care?

Family

Personal questions about their family:

What is the worst thing about being a middle/only/oldest child?
How much time do you spend with your family each week?
Which family member are you the closest to?
Who do you call on the phone the most often?
What do you wish you could change about your childhood?
What is your favorite family tradition?
Do you want a family of your own?
How did your parents meet?
How did your grandparents meet?
Have you ever been to a family reunion?
How does your family handle arguments?
Do you ever wish you had more siblings?
Who do you consider your family that isn’t actually related to you?
Does your family pressure you to act a certain way? Or do they support your decisions?
Did you have a curfew when you were younger?
Which family member do you look like?
Are you good with children? Do you want any of your own?

Negative questions to avoid asking family members to answer:

Did you lose anyone during the Covid 19 pandemic?
Are you pregnant?
Why are you still single?
Why are you still working at that job?
How many people have you slept with?
When are you going to settle down?
When are you going to have children?
Why aren’t you with your ex anymore?
When’s the last time you got laid?
Are you really wearing that tonight?
Have you had cosmetic surgery?
Are you wearing makeup?
Why are you so dressed up?
Are you going to eat all that?
Who did you vote for in the election?

Love

Sample questions about love and relationships:

What is your biggest pet peeve when it comes to dating?
What is a good way to express love, in your opinion?
Who was your very first celebrity crush?
Do you believe cheaters can change?
When did you have your first kiss?
What gives you butterflies?
What’s the best pickup line you can come up with off the top of your head?
Where is your favorite first date spot?
Who is your favorite fictional couple?
Are you close friends with any of your exes?
Have you ever broken someone’s heart?
How do you feel about sharing your password with your partner?
If you are in a bad mood, do you prefer to be left alone or have someone cheer you up?
How would you describe your first crush?
Do you believe in second chances?
What are your thoughts on online dating?
Is flirting cheating?
Would you go through a partner’s phone if you could?
What’s the biggest lie that a guy or girl you were dating has told you?
What is your love language?
What zodiac sign do you usually have the most chemistry with?
What zodiac sign do you usually clash with completely?
If someone hit you with a flirty pickup line, how would you answer?

Examples of a flirty question to ask a guy:

What is my sexiest personality trait?
What is the craziest thing you’ve ever done in bed?
Where’s your favorite place to be kissed?
What is your naughtiest fantasy?
What is your favorite sex position?
Where is the most adventurous place you’ve had sex?
What’s your favorite song to listen to during sex?
What color underwear are you wearing right now?
What’s your idea of the perfect date?
Have you ever touched yourself while thinking of me?
Are you going to save our text conversation to reread later?

Examples of a direct question to ask a guy you like to make your crush obvious:

What are you looking for in a relationship?
Do you have a specific type?
Do you prefer blondes or brunettes?
Do you like to cuddle?
If we went to the movies, what would you want to see?
If we went bowling, do you think you could beat me?
Do you have my number in your phone?
Did you see my latest selfie on Instagram?
Are you over your exes or still healing?
Are you free this weekend?

Wild questions to ask during a questions game at a party:

Have you ever gone skinny dipping?
Have you ever worn handcuffs in the bedroom?
Have you ever played strip poker?
Do you have any hidden tattoos or piercings?
What is the hardest drug you’ve ever done?
What was the drunkest you’ve ever gotten?
What is the most embarrassing thing that’s happened to you in the bedroom?
Have you ever been to an adult toy store?
When was the last time you wore lingerie?
Have you ever visited a strip club?

Values

Examples of a personal question about a person’s values:

Have your priorities changed since you were younger?
What is one behavior you refuse to tolerate?
What is the most important personality trait that you look for in a friend?
What does a healthy relationship look like, in your opinion?
Do you consider love or money more of a priority?
What was your biggest blessing in disguise?
What did you learn from your last relationship?
What bad habits do you wish you could change?
Does honesty or loyalty mean more to you?
What values did your parents instill in you?
What is an example of a toxic personality trait?
Do you consider yourself a good person?
Have you ever lied to protect a friend or family member?
What material things must exist in your life for you to feel fulfilled?
What is the greatest lesson a teacher ever taught you?
Do you have any regrets about how you’ve treated people in the past?
When was the last time you did a good deed for someone?
What do other people prioritize that you believe is overrated?
What personality trait do you value the most in a friend?
What do you believe your purpose in life is?

Aspirations

Examples of a simple question to ask about someone’s aspirations:

What is on your bucket list?
What makes you feel empowered?
What do you wish you accomplished by now?
Where was your favorite place you’ve ever worked?
What makes you feel the most accomplished?
Who are your role models when it comes to your career goals?
What inspires you when you’re low on motivation?
Out of all your friends, whose accomplishments do you admire the most?
How are you going to make the world a better place?
What kind of example do you want to set for the younger generation?
Are you the kind of person who leads or follows?
What are you the most passionate about in life?

Examples of a great question about making and breaking intentional habits:

What bad habits are you trying to break right now?
What bad habits are dealbreakers for you in a relationship?
What positive habits are you trying to form?
When was the last time you broke a bad habit?
Did you inherit any of your bad habits from your parents?
What is your worst habit when it comes to dating?
What is your best habit when it comes to dating?
What habit have you tried to break multiple times, but have never been successful?
What habits do you want to instill in your children?
What do you think the most important step to breaking a habit is?

Deep

Examples of a deep question to ask:

What is your biggest regret in life?
What is the biggest challenge that you’ve overcome in life?
How do you think you’re going to die?
What scares you the most about the future?
What book has had the most profound impact on you?
What makes you feel alive?
How do you want to be remembered?
What do you want to have written on your tombstone?
When was the last time you felt vulnerable?
What do you take for granted?
At what point in life were you the happiest?
What emotion do you experience the most?
What is a dream you’ve never said out loud?
What do you find yourself lying about the most?
Is it easy for you to show yourself love or speak kindly to yourself?
What do you use to cope when you’re feeling uncomfortable?
Who is the first person you call when you’re in trouble?
What are you most grateful for in your life?
Do you usually follow your heart or your head?
Did you ever judge someone for the dark secrets they told you?
How long does it take you to trust someone?
What do you do when you’re angry?
What was the worst phase of your life?
When have you felt your biggest adrenaline rush?
What do you hope to have achieved by 50?
Is there an opportunity you turned down that you secretly wish you’d have taken?
Is there a time or event in your life that you wish you would’ve appreciated more?
What do you miss about being a kid?
What’s the most spontaneous thing you’ve done lately?
When was the last time you lied about being fine and why?

Philosophical

Examples of an interesting question to ask during a conversation:

Would you sacrifice yourself for another person? Who?
When is it okay to break the law?
What do you want your last words to be?
When was the last time you pushed yourself to your limits?
Do you believe street smarts or book smarts are more useful?
Do you think artificial intelligence is going to overpower us?
Is privacy a human right?
Are people mostly good or mostly evil?
Do you believe immortality would be worth it?
What is the difference between living and existing?
Does a person’s name influence the person they become?
Does hardship actually make a person grow stronger?
Is humanity headed in the right or wrong direction?
What do you contribute to society?
What do you think your future self will remember about this period of your life?
How do you define consciousness?
Would it be more frightening to discover that humans are the most advanced species in the universe or that we are far from being the most advanced species in the universe?
Why do humans have such a strong urge to distract ourselves from the real world?
What’s the difference between justice and revenge?
What would be the most ethical way to give away five million dollars?
Are all individuals morally obligated to save another person’s life if they are able?
Does anonymity encourage people to misbehave or does it reveal how people would choose to act all the time if they could?
Why are humans so fascinated by mass murderers if their actions are universally considered evil and vile?
Is it better to be a big fish in a small pond or a small fish in a big pond?
If you could teach everyone in the world one concept, what concept would have the biggest positive impact on humanity?
Is it more important to help yourself, help your family, help your society, or help the world?
Is it wrong to spend money on expensive food when people are dying of hunger?
Can computers be creative?
If lying is wrong, are white lies okay?
What is the meaning of life?

Religion

Existential questions about religion and the afterlife:

What religion do you practice?
What do you believe happens after someone passes away?
What is your favorite quote from a religious text?
How often do you pray?
Which religious holidays do you celebrate?
Are your parents also religious?
If you believe in heaven, what do you think it looks like?
If you believe in hell, what do you think it looks like?
Do you care if your friends practice different religions than you?
Could you date someone who practiced a different religion than you?
Are you planning on passing down your beliefs to your children?
How are you going to answer your calling in life?
When do you feel the most connected to a higher spirit?
How has your faith helped you?
How has your faith hurt you?

Life

Follow up questions to ask younger children and teenagers about life:

Are you a good student?
Have you ever flunked a quiz?
Have you ever gotten detention?
Do you have any nicknames?
What’s your favorite phone game?
What are the best filters to use on social media photos?
What shows is everyone at school watching right now?
Have you read any good books in class lately?
Who is your favorite teacher?
What fashions are popular nowadays?
What is your favorite new slang word?
Do you put more energy into making friends, dating, or getting good grades?
Are you taking any classes that you wish you could drop out of?
Do you feel like the grading system is fair?
Do you prefer texting or talking to people face-to-face?
Do you feel pressured to look perfect on social media?
What do you wish your parents understood about you?
Do you think you’re given too much homework?
What is your favorite thing to do on weekends when you’re by yourself?
Do you know what you want to do when you’re older?

Examples of a leading question that will guide a conversation and give you the answer you want:

You live in my town, don’t you?
You have a dog, too, don’t you?
You’re a fan of (insert band), right?
You’re obsessed with animals too, aren’t you?
We’re in the same classes, aren’t we?
You’re a coffee addict too, right?
You’re my age, aren’t you?
You watch (insert show) too, don’t you?
We have a friend in common, don’t we?
You’re into (insert sport) too, right?

Career

Casual questions to ask about a friend’s career:

What is your dream job?
When you were little, what did you want to be when you grew up?
What has been your greatest accomplishment in life?
What’s the most embarrassing thing you’ve said during a job interview?
Have you ever sent the wrong text to one of your employers?
What’s your favorite thing about your current job?
Who is your favorite coworker?
Would your younger self be proud of what you’re doing now?
What career advice would you give your younger self?
Are you proud of yourself? Why or why not?
What does success look like to you?

Examples of an open ended question to ask when speaking to a customer:

What are your thoughts?
What concerns do you have?
What is most important to you at the moment?
What challenges are you facing?
What would you change about your current situation?
Where do you turn for inspiration?
What are your top priorities?
What goals would you like to accomplish?
Where did you look before coming to our store?
How can we make this webpage/store better?

Examples of a job interview question you might be asked to answer during an interview:

What is your salary expectation?
Why do you believe you’re a good fit for this company?
What’s an example of a time you went above and beyond for a customer?
What is your greatest asset as a team member?
Where do you see yourself in the next few years?
What is your greatest weakness?
Why are you leaving your current position?
What interests you about this role?
Do you know how to properly use any internet device?
What motivates you to work your hardest?
As your interviewer, do you have a specific question you want to ask me?

Questions you should ask during an interview about company culture:

What do you consider the greatest benefit of working here?
What is your favorite thing about being a hiring manager?
What role do you play at this company?
Has your role changed since you’ve been here?
What can someone do to impress you during the interview process?
Who will I, and the other participants, report to directly?
What are the common career paths in this department?
What’s your least favorite part about working here?
Can you tell me about the last team event you did together?
Where do you see this company in the next few years?