Questions to ask to start conversations

If you could jump into a pool full of something, what would it be?

What do you want to be remembered for?

What are your secret skills?

What was your favorite childhood toy?

What was the best gift you’ve ever given to someone?

What is the most embarrassing that happened to you in primary school?

What would you grab if your house was on fire?

What is your destination for the trip of your dreams?

When you were little, what did you want to be when you grow up? And do you still want it?

If you got stuck in the elevator and was forced to listen to only one song, which would it be?

What is the best advice anyone has ever given you?

Which social game was your favorite while growing up?

If you could live anywhere, where would it be?

How do you treat people who annoy you for no reason?

What have you learned from your past relationship?

What is the most important thing that guys should understand about the girl, and it seems to you that they do not understand?

Who is your best friend?

With what phrases were guys trying to conquer you with?

What random stranger has had the biggest impact on your life?

What achievement are you proud of but most people would consider silly or weird?

What period in history had the best fashion?

What silly or funny thing makes you afraid or creeps you out?

How quickly do you jump to conclusions about people?

What is something you think you will regret in the future not starting now and what is something you already regret not starting sooner?

What’s the worst and best thing about being female?

If you could replace the handshake as a greeting, what interesting new greeting would you replace it with?

When does time pass fastest for you and when does it pass the slowest?

What pictures or paintings have had a big impact on you?

What movie or book character are you most similar to?

You can broadcast one sentence to every tv channel and radio in the world and have it translated to each country’s language. What sentence do you say?

What fact are you really surprised that more people don’t know about?

What memory do you just keep going back to?

What’s the most immature thing your parents do?

Who haven’t you seen or talked to in a long time and hope they are doing okay?

Where is the last place you would ever go?

What’s something that you’ve never been able to do well?

What’s the most ridiculous argument you’ve had?

What’s the biggest lesson life has taught you?

What’s the weirdest tradition your family has?

What is your very first memory?

What’s the most embarrassing thing you’ve said or done around someone you had a crush on?

What doesn’t exist but you desperately want / need it?

If you could hear every time someone said something good about you or something negative about you, which would you choose?

What do you wish you could re-live?

What’s something weird that you recommend everyone trying at least once?

What’s the best gag gift you’ve ever seen or gotten?

Do you prefer being warmed when you’re too cold or being cooled when you’re too hot?

How decisive or indecisive are you?

What piece of culture or trend has died out, but you would like to see it make a comeback?

If you inherited a private jet from a stranger, what would you do with it?

What’s something from your childhood that used to be common but now is pretty rare?

What snack can you just not get enough of?

What was the worst phase you went through?

If you were an action figure, what accessories would you be sold with?

What options would come up if you could “right-click” people?

What do you like to do that is traditionally considered masculine?

What’s something you learned recently that you really should have already known?

What’s the best practical joke you’ve pulled or seen pulled?

What’s this time period the golden age of?

What country can you name but besides the name you know almost nothing else about it?

Who do you make happy?

What’s an innocent mistake you made that had dramatic consequences?

What’s in your pockets right now?

What do you think people automatically assume about you when they look at you?

Looking back on your life, what have you done that has given you the most satisfaction?

If you were forced to create a new dance move, what would it be and what would you call it?

What do you really wish you knew when you were younger?

What songs can you sing that I’ll know after hearing two words from the song?

If you were given $100,000, but it could only be used to upgrade your shower or bathtub what upgrades would you make?

When was the last time you laughed so hard you cried?

What do you wish you had more time for?

When was the last time you had a gut feeling about something that turned out to be correct? How about a time your gut feeling was wrong?

What would you do if one day you woke up and every person was just gone without a trace?

What’s your “and then it got worse” story?

What’s your curiosity killed the cat story?

What’s the biggest lie that someone told you?

What would be the worst thing to put into a piñata?

What’s the most unpleasant sounding word?

What was a huge deal when it happened but now everyone seems to have forgotten about it?

If many people consider red to represent anger / passion, blue sadness, green envy, what feelings would some of the other colors like purple, turquoise, silver, or brown represent?

What’s the weirdest thing you have seen on someone’s phone?

What’s your favorite way to meet new people?

What areas in your life do you have high hopes for and what are those high hopes?

Who was the most spoiled person you personally have met?

What’s the most pleasing accent to hear your language spoken with?

Who is or was your greatest rival?

What’s your favorite non-drug / non-alcohol high?

What’s the worst thing you’ve heard one person say to another person?

How do you feel about books?

What do you really want to know?

What was your most memorable dream or nightmare?

What do you love about yourself?

What cheesy song do you love?

What’s the most ridiculous thing you have convinced someone is true?

What event would you like to know the whole and complete truth about?

What have you recently become obsessed with?

What’s the biggest waste of money you’ve seen?

What’s surprising about you?

If you could only wear one outfit for the rest of your life, what would it be?

What are some outdated customs that don’t make sense anymore, but people still follow them simply out of tradition?

What would be the cutest infestation to have in your home?

What was the last disaster you prevented?

When you were a kid what silly thing were you deathly afraid of?

Besides a raise or more vacation time, what’s the best perk a company can offer employees?

Where do you like going for walks?

If you found out you would inexplicably fall down dead in one year, what would you change about your life?

What’s the most rage inducing thing you’ve had to make or put together?

What movie have you seen more than seven times?

What’s the worst example of curiosity killing the cat you’ve seen?

What skill do you wish more people took the time to learn?

What would be the scariest text message to wake up to?

What’s something that actually happened but seems absurd and unrealistic?

What personality traits are people proud of but shouldn’t be?

Most people want to be wealthy for one reason or another. Why do you want to be wealthy? What would be the biggest benefit of being wealthy?

What type of design style do you like most? From architecture, interior design, art, cars, phones or whatever.

What kind of personality traits do you associate with certain names?

What’s romanticized in modern culture but really shouldn’t be?

What’s the worst book you’ve been forced to read in school?

What always lets you down and what never lets you down?

What’s the best thing you could tell someone to cheer them up when they are feeling down?

When you were a kid, what movie did you watch over and over again?

If you could look through one person’s email without them knowing, whose email would you spy on?

When was the last / best time that someone said something they thought you couldn’t hear or understand but you could?

What’s something you completely changed your mind about and went from believing one thing to believing the exact opposite?

What’s the worst trait a person can have?

What’s going to be the next retro thing that comes back into popularity?

What would you do if you knew for a fact that world war three was going to start in three months?

If you could know one truth about yourself, history, the world, or even the universe, what truth would you want to know?

What’s something that no one wants to hear, but everyone should?

What can you talk all day about?

What are you hyped about?

What was the most disappointing ending to a great book / movie / game?

What’s your favorite souvenir that you have?

What piece of clothing have you seen that you desperately wanted?

What’s your best ethically gray life hack?

What’s your reason for getting out of the bed in the morning?

What would you do if someone left a duffle bag filled with $2,000,000 on your back porch?

If everything in your house had to be one color what color would you choose?

Assuming you name inanimate objects, what are some names for inanimate objects you own or have owned? (I.E. Cars, computers, shoes, etc.)

What question have you always wanted to ask, but were too afraid of looking stupid?

What would your warning label say if every person was required to have one?

What weird childhood fear do you still kind of hold on to?

If you went into a coma and woke up in the year 2120, what would be the first thing you would want to know?

What’s the best decision you’ve ever made?

What’s the most embarrassing thing that has fallen out of your bag?

What’s the funniest thing you’ve seen a relative do?

What’s something that only someone from where you grew up would understand?

What would make the world more interesting if it was a different color?

What do you think about in the shower?

What’s the best ice cream topping?

What makes someone a “good” person?

What’s the dumbest thing you’ve done in the last 24 hours?

When were some occasions you did a double take?

What would the trailer to a movie about your life be like?

What kind of old person would you like to become?

What do couples do that seriously annoys you?

If you could custom design an organ for yourself, what would it do and where would it go?

If you had to choose your spouse based on just one question, what question would you ask?

If money wasn’t an issue, what company do you think would be fun to work at?

What’s the most polarizing question you could ask a group of your friends?

If you were a scam artist, what scams would you run?

Who out of everyone still alive would you most want to share a meal with?

What would your perfect room look like?

What skill would you most like to master?

What would be the most amazing adventure to go on?

What pets did you have while you were growing up?

What’s your favorite day of the year?

How do you relax after a hard day of work?

What’s the farthest you’ve ever been from home?

Where is the most interesting place you’ve been?

What’s the best thing that happened to you last week?

If you could keep any animal as a pet, what would you choose?

If you could turn any activity into an olympic sport, what would you have a good chance at winning a gold medal for?

What’s the most useless talent you have?

What’s the most illegal thing you’ve done?

What would be your spirit animal?

If you had a personal flag, what would be on it?

What are you really good at, but kind of embarrassed that you are good at it?

What was the most memorable gift you’ve ever received?

What word or saying from the past do you think should come back?

How about the best person to be stuck in an elevator with?

Have you ever had a crush on a fictional movie character? Who?

What’s something you thought you’d grow out of but haven’t?

As the only human left on earth, what would you do?

How different was your life one year ago?

What is your best childhood memory?

What’s something you’ve always wanted to try?

What is the most heartwarming thing you’ve ever seen?

What’s something you love, that people haven’t even heard of?

What was your worst first (and last) date?

If you were the ruler of a small island nation, what would you do?

What could you give a 40-minute presentation on with absolutely no preparation?

What is something that is considered a luxury, but you don’t think you could live without?

What would be on the gag reel of your life?

If you could know the absolute and total truth to one question, what question would you ask?

If you could witness any event of the past, present, or future, what would it be?

If you were president, what is the first thing you would do?

What is your favorite feature on the opposite sex?

If you could go back in time and delete the internet from existence, would you?

If you could bring back any trend from the past, what would it be?

If you were given a one-minute ad slot during the super bowl, what would you fill it with?

What’s something your brain tries to make you do and you have to will yourself not to do it?

What problem or situation did tv / movies make you think would be common, but when you grew up you found out it wasn’t?

Which fictional character would be the most fun to meet in real life?

What reality show doesn’t exist, but really should?

What’s the worst food combination you can imagine?

What’s the most bizarre set of items that you could buy to make a cashier uncomfortable?

If you won the lottery, how would you quit your job?

What position do you sleep in?

What would be your perfect breakfast?

What is the longest you’ve gone without sleep?

What do you spend the most time thinking about?

What is something you will never do again?

Where is the most relaxing place you have been?

What is your favorite piece of technology that you own?

What’s the most refreshing thing on a hot summer day?

What is your favorite holiday?

Time freezes for everyone but you for one day. What do you do?

What is the most terrifying animal of all time?

What are some things that you’ve never bought and will never buy?

What food would be the best to make a house out of?

What is the ugliest thing you own?

What view would you most like to have out of your window?

What was the strangest gift you’ve ever received?

What is the sexiest and least sexy name?

What are you looking forward to in the next few months?

What website do you visit most often?

Where would you spend all your time if you could?

What are you most likely to become famous for?

What question can you ask to find out the most about a person?

What is the most unusual conversation you’ve ever had?

Among your friends or family, what are you known for?

In your group of friends, what role do you play?

What were some of the turning points in your life?

When do you feel truly “alive”?

What’s the last adventure you went on?

What makes a good life?

What irrational fear do you have?

What personality trait do you value most and which do you dislike the most?

If you had to change your name, what would you change it to?

What’s something horrible that everyone needs to try at least once?

What does a perfect day look like to you?

What are your top three favorite books and why?

If you could only keep five possessions, what would they be?

If you could travel anywhere, where would you go and why?

If you could only live in one, outdoors or indoors, for the rest of your life, which would you choose?

Do you like to stay in touch with people that have moved away or do you have a tendency to forget all about them?

Who responsibility is it to keep things nice and romantic in the relationship – him or her…?

Have you ever been through an experience that you couldn’t explain?

How do you relax and de-stress when you are having a hard time?

If you could have a video of any one event in your life, what event would you choose?

What chance encounter changed your life forever?

What incredibly strong opinion or belief do you have that is completely unimportant in the grand scheme of things?

What’s the best and worst thing about getting older?

What do you wish you could tell yourself 10 years ago? What do you think you’ll want to tell your current self 10 years from now?

What are the top three things you want to accomplish before you die? How close are you to accomplishing them?

What bends your mind every time you think about it?

If you could make a 20 second phone call to yourself at any point in your life present or future, when would you call and what would you say?

What’s the title of the current chapter of your life?

Who, besides your parents, had the biggest impact on your life?

Why do you think we dream?

What are you afraid people see when they look at you?

What bridges do you not regret burning?

If you could make one rule that everyone had to follow, what rule would you make?

If you could steal one thing without consequence what would it be?

Are you the kind of friend you’d want to have as a friend yourself?

What has been the best decision you’ve made in your life so far?

Do you believe love can last a lifetime?

Do you think it’s better to know a lot about one thing or a little about many things?


Describe the person(s) you hoped/imagined you’d meet when you came here.

Leave a Reply

Your email address will not be published. Required fields are marked *