I often get asked by our readers:
“What are good questions to ask friends?” and “What are funny questions I can ask someone?” “What should I ask to get to know someone?”
We decided to go ahead and make a mega list of not 100, not 200, but 301 funny, deep and interesting questions to ask a friend, someone you want to get to know better, or just to have fun.
General conversation starters
Nice to meet you, what’s your name?
How do you know people here?
What brings you here?
Are you from around here?
Do you come here often?
What do you think of this place?
I just love the weather around here, is it always like that this time of the year?
How was your trip here?
I don’t know if we’ve met before?
Starting a conversation on the street
Excuse me, do you know what time it is?
How do I get to [place or street]?
Do you have a recommendation for a good cafe around here?
Where’s a good place to go if you want to see the city from above?
Getting to know someone you just met
What do you do?
What do you like the most about your job?
Is your current job what you expected it to be?
What are you doing in school right now?
What do you do when you’re not working?
Do you have any siblings?
What do you like the most about living here?
You prefer living in the countryside or in a city?
Do you prefer to visit people or bring them over?
Would you ever want to live in another country? Why?
What would you do if you didn’t have to work?
Do you prefer movies that make you think, or the ones that let you relax?
How do you feel about being away from home when traveling?
Do you like prefer board games or video games?
Do you like guns? What’s your favorite one?
Do you enjoy how hectic the holidays feel sometimes or do you dislike it?
Are you into sports?
What’s your favorite music genre?
Do you follow someone on Youtube?
Do you have a TV at home?
Do you like cooking? What’s your specialty?
Do you prefer big parties, or the ones where everyone knows each other?
Small talk questions
What do you like the most about this city?
How do you like the party so far?
What are you doing in this city?
Did you hear about this new place they opened around here?
Do you know what the weather will be like today?
Did you hear [story] on the news today?
Did it take you long to get here today?
How’s the house renovation coming along?
Why did you decide to come to this event?
Do you think it’s going to rain today?
How was the vacation? Where’d you go?
How are the kids?
Remember how I mentioned [something you mentioned before]? Well, guess what happened?
Have you seen any good movies lately?
What are your plans for the weekend?
Do you know any good gyms here in the city?
What’s your favorite color?
Do you like thrillers?
How was your weekend?
What do you usually do in your free time?
How do you guys know each other?
Do you ever go to any kind of live shows?
Do you follow the news? Have you heard anything interesting lately?
Have you read any good books lately?
Do you watch [Insert TV-show]?
What’s one spot that I should definitely visit in this city?
Do you have any pets?
What food do you like the most?
What’s the first thing you’d do after winning the lottery?
What’s the silliest thing you’d do if you had unlimited money?
What’s your most frustrating moment at work?
If you had the power to create one thing perfectly, just as you imagined it, what would it be?
Do you ever feel like you’re in a movie?
If you were the leader of a band, what’d you call it, and what kinda music would you play?
An all-out war between cats and dogs: who wins and why?
Would you rather fight a horse sized duck or 100 duck sized horses?
How’d you feel if you couldn’t use your smartphone for a year?
Pizza or tacos?
Salt or sugar?
How many five-year-olds could you fight at the same time?
If you were an animal for a week, who’d you be, provided that you’d survive?
So what came first, the chicken or the egg?
If you owned a gay bar, what would you call it?
What would you call your autobiography?
If you could only celebrate one holiday, what would it be?
Questions to ask at parties, dinners, bars or clubs
Hey, what’s your name?
Do you want a drink?
What’s that you’re drinking?
How many drinks are you on?
The cake is delicious, have you tried it?
What’s your favorite thing here so far?
Have you tried the [a food or drink on the table]?
Do you know what song that is they’re playing?
Is it always this many people here?
Do you like dancing?
Do you know anyone here?
How do you guys know each other?
What do you think about the music?
How long do those parties usually last?
Do you come here often?
Do those parties happen often?
Do you like it here?
Did you come here alone?
Getting closer to someone you’re acquainted with
What kinda relationship did you have with your parents growing up? Did it change much since then?
Where would you rather live if money wasn’t a problem?
Did you ever wish you had a different name?
Did you listen to your parents when growing up?
Did you have any hobbies as a kid that you stopped doing?
What’s your favorite holiday?
Did you ever cheat on an exam?
What’s the most important thing in a friend to you?
What’s your favourite time of the day/year?
What do you think is your best feature, appearance wise?
Do you keep in touch with your classmates from school or the university?
What do you love the most in life?
What’d be your next option for a career?
Do you believe in aliens?
Do you have a dream which you have no intention of pursuing?
Is it easy for you to make friends?
What’s your first memory in life?
What do you dislike in people the most?
What do you like the most in people?
How would you rate your own intelligence?
Have you planned your retirement?
Do you vote?
What can you not tolerate?
What’s one thing everyone seems to love that you just don’t get?
What do you think about universal basic income?
Questions for your best friends
What do you remember as the best moment of your life?
Which song do you feel describes you the most?
Do you ever give money to the beggars?
Do you think violence on TV affects people?
Why do you think we’re friends?
When did you last sing to yourself? To someone else?
Have you ever had health problems?
What’s your worst injury ever?
Given the choice of anyone in the world, whom would you want as a dinner guest?
Do you exercise for the appearance, for the health benefits, or for the fun of it?
Do you have any regrets? What would you change if you could do it all over again?
What is it that you’d like to tell someone but can’t?
What scares you about the future?
What makes you absolutely lose your mind?
Do I have any habits you absolutely hate?
Would you like to be famous? In what way?
Was it mutual the first time you fell in love?
What’s the funniest school story you can recall?
What’s the most embarrassing thing you’ve ever done?
Is there anything you wanna do together that we never do?
What’s your most treasured possession?
Is there anything you currently miss in life that you used to have?
Do you feel fulfilled in life?
Before making a telephone call, do you ever rehearse what you are going to say? Why?
Did you ever feel old as a teen?
Do you feel old?
What would you change about the way you grew up?
Name three things you and your boyfriend/girlfriend seem to have in common.
How old do you think you’ll be?
Did you ever plan to do anything bad to someone?
What would constitute a “perfect” day for you?
Is there anything you dislike about me? If so, what could I do better?
What do you enjoy the most about being around me?
What’s one thing you feel like people don’t appreciate enough about you?
Have you ever been in a toxic relationship?
Do you have a secret idea about how you will die?
Did you ever pray for something fantastic or silly to happen?
Is there any responsibility you don’t want to have?
What are you the most thankful about?
Would you rather-questions
Lose an arm or a leg?
Get rich of marry happily?
Uncontrollably laugh for an hour per day or uncontrollably cry for 20 minutes per day, at random times?
Uncontrollably dance or sing at random times during the day?
Forever quit drinking unhealthy beverages or eating unhealthy food?
Go blind or deaf?
Crack a bottle over your own head, or someone else’s?
Be able to text only, or to call only?
Play Russian roulette with Hitler using 1 or 2 bullets?
Always lie or always tell the truth?
Pee yourself when you’re alone with your boyfriend\girlfriend or in front of 100 strangers?
Be forced to hop around on one foot or run on all fours for the rest of your life?
Drink raw eggs or eat raw meat?
If you’d stay the same age as you are now, would you rather go back to school or retire right now?
Knowing the exact date you’d die or die suddenly without warning?
Write a bestseller book or release a hit song?
Spend 5 years as a working slave or as an inmate in a maximum security prison?
Go trick-or-treating wearing a superhero costume or a “dog wearing a hot dog” costume?
Spend a year in a coma or living 6 months with the person you hate the most?
Lose a middle finger on your left or right hand?
You are far from the civilization and your horse is injured. Do you kill it to put it out of its misery or leave it to suffer?
Be rich and spend your life in one city, or be poor but see the world?
Binge-watch all the seasons of a show you hate, or watch one episode per day?
Write music or play it?
Slap your mom or slap your dad?
Go homeless for five years or be poor forever?
Be burned at a stake for witchcraft or die from dementia?
Truth or dare questions
Did you ever not make it to the bathroom on time?
Did you ever get so drunk you didn’t remember what you were doing the next day?
Did you ever try any drugs?
What was your nickname in school?
What’s the worst thing you’ve ever done?
Your most disgusting habit as a kid?
Did you ever talk about your friends behind their backs?
When did you steal the last time, and what was it?
Did you ever want to kill someone?
Have you ever hooked up with someone without knowing their name?
How many people have you slept with?
Have you ever kissed a person of your own gender?
What’s one thing you can’t control in your life?
Did you ever run away from home as a kid?
What’s the worst thing you called your mother?
What’s the worst thing you’d do for a million dollars, provided you don’t get caught and nobody ever knows about it?
Did you ever end up naked in a public place?
What’s one thing you do despite it going against who you really are?
Do you often go out without any underwear on?
Have you ever cooked a meal for someone else from expired products?
Would you marry one of the top 100 wealthiest people in the world if you didn’t like them?
Deep questions to ask close friends
What do you struggle with the most?
Do you feel like part of society?
What do you think about using population control to prevent overcrowding our planet?
If a genie could tell you a truth you’d like to know about yourself, what would you want to know?
Who’s your favorite family member?
How is your relationship with your parents?
What’s something you’d like to tell your parents that you would never dare to?
What’s something you’d do if you know you’d get away with it and no one would never know that it was you?
Is there something you’ve wanted to do for a long time but haven’t yet? What would that be?
What do you think about freedom of speech?
What do you think about abiding the law vs. following your own moral code?
How would you feel if your spouse was in love with another person?
Do you find constant physical and mental comfort important, or do you prefer to challenge yourself often?
Would you rather harm yourself, or others around you?
Do you think there is an afterlife of any kind?
Would you commit suicide if you saved the life of 1 other person? 2 people? 5? 10?
How do you think porn affects our society?
Should all drugs be made illegal, or all of them made legal?
What do you think about veganism?
What kind of role does religion play in your life?
Have you ever wanted to die?
How would you prefer to die?
Are you into politics?
What’s the point in living, if you’ll end up dead anyway?
What do you think is the meaning of life?
Do you feel like men and women are equal?
What’s your best memory?
What’s your worst memory?
When was the last time you cried?
If you knew that you were to die suddenly, what would you do?
What does love mean to you?
Is there ANYTHING that’s too serious to joke about? What would that be?
What’s something you think that you think no one else thinks?
What’s the angriest you’ve ever been? What happened?
Could you bring yourself to kill someone in self-defense?
If you could ask the reaper to spare your loved one, what would you tell him?
In which situations do you think war is called for?
If you ended up in a coma for 10 years, still conscious but unable to communicate, would you want them to pull the plug?
If you had to pick one, who in your family would you miss the most if he or she died?