Ultimate Q&A: 270 Good Questions to Ask When Starting a Conversation With Anyone

Entertainment By James 

Ultimate Q&A: 270 Good Questions to Ask When Starting a Conversation With Anyone

Entertainment By James 
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It’s ok if you get a little nervous meeting someone new whether it is a girl, boss, or a complete stranger; it happens to the best of us! Maybe you are a typical talker, but have you ever found yourself in a situation where small talk seems to fail?  You’ve talked about the weather.  You’ve done the “where are you from” and “what do you do” lines, and the conversation is just not going anywhere.

Well, if you really want to connect with someone beyond the superficial, it helps to have some questions on standby that you can pull out in any situation.

This handy list of questions covers all types of relationships and occasions.  These are things you can ask a coworker when work is slow.  You can entertain your family for a long road trip.  Spring one on your buddy at the bar or ask your partner on the next date. After all, having a great conversation not only shows your intellect and interest but that you care about the person on the other end.

Table of Contents


  • Best Ice Breaker Questions
  • Best Questions for Conversation Starts
    • Life Goals
    • Animals
    • Modern World
    • Career
    • Skills and Hobbies
    • Entertainment
    • Travel
    • Food and Drink
  • Best First Date Questions
  • Best Get to Know You Questions
    • Personal
    • Deep
    • Hypothetical
    • Existential
  • Best Questions to Ask a Friend
  • Best Questions to Ask a Girl
  • Best Questions to Ask a Guy
  • Best Questions to Ask a Girlfriend
  • Best Questions for Couples
  • Best Weird Questions
  • Best Random Questions
  • Best Interesting Questions
  • Best Funny Questions
  • Best Fun Questions
    • Best Would You Rather Questions
    • Best This or That Questions
    • Best Truth or Dare Questions
    • Best What If Questions


Best Ice Breaker Questions


  1. What good happened to you today (or this week)?

It is always good to start on a positive note both in your conversation and overall thinking.


  1. What did you have for dinner last night?

As Anthony Bourdain said, “You learn a lot about someone when you share a meal with   them.”


  1. What do you do for a living?

This one is the standard ice-breaker question. Although it might seem pretty standard, it   is a must for strangers. After you get it out of the way though, focus on more exciting    topics.


  1. What responsibility would you gladly give up? What would you not give up?

Good insight into what a person values or doesn’t value. While daily chores and weekly tasks can be mundane, would you really want someone else to do those things in your place? Think about it for a second…


  1. What would be your ideal way to spend the weekend?

Remember the answer for when you make plans together.


  1. What do you like best about your house or apartment?

Is there a great view? Plenty of kitchen space? Best shower head ever?


  1. What is your middle name and what’s its significance?

Whether named after a great-grandparent or mom’s favorite musician, it’s always an         interesting story.


  1. Where is your happy place?

It’s that place you always want to be when your soul needs a lift. Maybe it was that one time you went on vacation to a tropical destination. On the other hand, those 10 minutes in the morning with just your cup of coffee and puppy before the rest of the world wakes up might be your perfect time.


Best Questions for Conversation Starters


  1. What was your most memorable birthday?

And the answer can help you plan future birthdays. Do you hate surprises? Should they    skip the cake next year for some macaroons?


  1. What would your perfect day be like?

Other than April 25th. We all know that is the best date because you just need a light jacket (Seriously, watch the always lovely Sandra Bullock in Miss Congeniality, please.)


  1. When are you happiest?

Whether trying to be a good boyfriend or just a good friend, you need to know what lifts others up. Listen carefully to the answers to these questions so you can become the best     person to those you care about the most.


  1. What’s something you could teach me about?

Always be willing to learn new things. Maybe now is not the time to be stubborn about    trying something new – at least the idea of it!


  1. Do you believe in luck?

Or fate? Or destiny? Or is everything just chance and happy accidents? So much to discuss all of a sudden, isn’t there?


  1. What’s the most useful thing you own?

What’s your personal Swiss Army Knife? Besides the cell phone.


  1. What is the first thing you notice about a person?

Eyes? Smile? Posture? Manners? None of the above.


  1. If you could have lunch with one person alive or dead, who would it be?

And you can’t say Jesus, MLK, or Gandhi.  Almost everyone says them. Maybe name off a couple of people if you have a bunch of role models and heroes.


  1. What is your favorite season, and why?

Maybe summer or fall. On the other hand, some might automatically think baseball season. Follow up your answer with what makes it so great.


  1. Do you have any guilty pleasures?

Listening to ABBA, binging true crime podcasts, or having the complete DVD box set of your favorite childhood show; we’ve all got guilty pleasures, and they’re nothing to be ashamed of.


  1. What’s the best single day on the calendar?

Why do you adore this calendar day? Perhaps it is a birthday, holiday, or within your favorite season.


  1. What are you interested in that most people haven’t heard of?

Feel free to get way too excited and go into detail.  Enjoying things is ok.


  1. What age do you wish you could permanently be?

Think about that perfect cross of youth and maturity.  Can you ever look young yet be wise at the same point in life? What a great age to stay at forever.


  1. What’s your dream car?

Whether it’s an all black 1970 Cadillac DeVille or a brand new Chevy Silverado with all the extras, a dream car says a lot about a person.


  1. What’s something you’ve meant to try but just haven’t gotten around to it?

The answer to this question could be the inspiration for the next date or birthday party.


  1. What amazing thing did you do that no one was around to see?

Like the time you made the high score on Galaga, but your buddies were on the other side of the arcade.


  1. What’s the best way to start the day?

It could be the sun streaming in through the windows, your morning run, or that splash of Bailey’s in your coffee.


  1. If you didn’t have to sleep, what would you do with the extra time?

Think of all the books you could read, or true crime shows you could binge.  Maybe you could finally get that project car running.


  1. What’s your favorite piece of clothing you own/owned?

Go ahead and admit you loved those sneakers that had the lights in the heel.


Life Goals


  1. What’s on your bucket list?

What are a few things that you absolutely must do while you have the time?  It could be climbing Everest, or finally reading War and Peace cover to cover.


  1. What are some of your long-term goals?

Maybe you want to get a Master’s or Ph.D. Write a novel and get it published? Play in a terrible punk band and smash your guitar?


  1. What goals do you have for the next five years?

Whether its school, career, hobby or family; it’s always great to have a vision for the future.


  1. What three habits will improve your life?

Don’t forget about the best way to put them into effect.  Goals without a game plan are just daydreams.


  1. How different was your life one year ago?

Other than being a year older; think about what you learned and how you’ve grown.


  1. What are you most looking forward to in the next ten years?

Some people want to start a family, some want to progress in their careers, and some want to gather life experiences.




  1. What animal would be your Patronus?

This type of animal holds a special place in your heart, whether it be your protector or the animal expression of your soul.


  1. Do you have/have you ever had any pets?

If not, what kind of animal would you want for a pet?


  1. What’s your favorite animal and why?

Did you know that opossums are almost totally immune to rabies, otters link paws when they sleep in the water, and skunks will only spray as a last resort to escape a threat?


Modern World


  1. If you were stranded on a deserted island and you could have only 1 item, what would it be?

Don’t forget to pack your favorite volleyball.


  1. Could you live without the internet?

Just wanted to point out the irony of reading this question on an article, found on said internet.


  1. What are some challenges you think the next generation will face?

Will we leave the world a better place than we found it?  Lots of things to think about here.


  1. What have you only recently formed an opinion about?

Admitting you don’t know something, and seeking knowledge is a sign of intellectual strength and curiosity.


  1. What is something that a ton of people are obsessed with but you just don’t get the point of?

It’s ok to admit you just can’t get into Marvel or Game of Thrones.


  1. What fad or trend do you hope comes back?

High-waisted jeans have made a massive comeback for women, but it seems the return of JNCOs hasn’t materialized yet.


Career Questions


  1. If all jobs had the same pay and hours, what job would you like to have?

Basically, what do you want to be when you grow up? This question really taps into your true passion in the world and might even hint to your purpose. It’s ok to have more than one answer.


  1. How do you relax after a hard day of work?

Are you a cold beer and Sportscenter kind of guy, or are you off to the gym or for a run? Maybe neither. You turn up some music and hit the peace pipe.


Skills and Hobbies


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

Now’s your chance to talk about that hidden talent. It might be a sports-related concept, but feel free to explain how you can fold a t-shirt perfectly in two seconds or touch your tongue to your nose.


  1. What job do you think you’d be really good at?

Hate to break the bad news, but there’s more to being a brewmaster than drinking beer all day. It should be something you wouldn’t mind doing over and over again, forever.


  1. What skill would you like to master?

Do you have a burning desire to be a master baker, master mechanic, or a multi-instrument musician? Maybe you already mastered something like a martial art.


  1. What hobby would you get into if time and money weren’t an issue?

Restoring cars, collecting art, traveling the world are all fun aspirations, but they don’t come cheap.


  1. How often do you play sports?

Team sports and individual sports count, too.  You can even debate if table tennis, chess, and curling count as sports.


  1. What is your favorite hobby?

Maybe you never thought about it because you just work and sleep all of the time, but when you do have a free moment, what one thing do you prioritize or dedicate your time to?


  1. What kind of art do you enjoy most?

Everything counts from Impression to Manga and more. Go ahead and drop artist names or exhibits you like. Perhaps you can visit a gallery together in the future.


  1. When was the last time you climbed a tree?

A feat that always seemed to be much easier when we only weighed 50lbs.


  1. Do you like to cook?

Or do you prefer sampling someone else’s creations? Keep an open mind that not all women like to cook!




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

Summer camp? Deployment? Vacation?  What was it like? Maybe you loved every second or was the experience scary and forced?


  1. Where were you living between the ages of 7 and 12? What were winters like then and how was your home heated during that time?

Every region treats winter differently.  Some places don’t really get snow and shut down after a dusting.  Other areas, like the Midwest, see blizzards as a personal challenge. It can be an interesting topic whether the other person can relate to your story, or are learning something new.


  1. Do you have any trips coming up?

Are they for business, personal, or maybe a bit of both?


  1. Where is the most interesting place you’ve been?

And what was it about the place that made it so interesting?


  1. On your last vacation, did you plan everything out beforehand or go with the flow?

Some of us are more spontaneous than others.  Do you like to hop in the car, pick a direction, and go or do you want an itinerary to maximize your day?


Entertainment Topics


  1. What songs have you completely memorized?

Could you nail it at karaoke night? We don’t recommend busting a tune right there in the middle of the conversation, unless you feel comfortable.


  1. What game or movie universe would you most like to live in?

Whether they want to live in Skyrim or Hyrule, the answer tells a lot about a person and their interests. Some people aren’t into sci-fi or fantasy genres, but they could still pick something unique like the universe where Zack Morris went to Bayside High.


  1. What TV show or movie do you refuse to watch?

Some folks find a character annoying or a premise silly, and that’s fine.  Not everyone has to like everything.


  1. What TV channel doesn’t exist but really should?

Admit it; you want a channel that plays nothing but old Puppy Bowl reruns. When you actually think about it though, there are a lot of channels that already exist.


  1. What movie title best describes your life?

The movie plot doesn’t have to fit your life, just the title. This moment might be perfect to show your silly side.


  1. What’s the best comedy movie you’ve ever seen?

It’s the one where the jokes never get old, and you always catch something new.


  1. What’s your favorite song and why this particular one?

It’s hard to pick just one but do your best.


  1. What’s been the best concert you’ve attended?

Were you lucky enough to catch Rush on their R40 farewell tour, or maybe you go to go to Warped Tour when they had the perfect line-up. On the other hand, maybe the Up In Smoke is more your flavor.


Food and Drink


  1. What’s your favorite drink?

Alcoholic or non-alcoholic, it might be tricky to pick just one! It depends on the setting sometimes.


  1. If you could only eat one food for the rest of your life, what would it be?

And why is that food tacos? If this question is too tricky, maybe pick a favorite dessert as well.


  1. What is your favorite meal of the day?

You can even bend the rules and go with breakfast for dinner.


  1. Where do you like to go when you eat out of the house?

Is it a high-end restaurant or a family-run place tucked away in an old neighborhood? Perhaps you prefer anything as long as you don’t have to cook from a fast-food burger to a lobster tail.


  1. Do you drink coffee or tea?

And how do you take your preferred drink?


Best First Date Questions To Ask


  1. If you could wave a magic wand right now and have your life be perfect, what would that new life look like?

Where would you live?  What would you be doing? Hopefully it is not too far off from what you have now.


  1. What could you spend all day talking about?

All right, let’s hear your Master’s dissertation.


  1. What’s your favorite thing about your best friend?

Certain character qualities bring people together.  It could be loyalty: the guy who’s got your back no matter what.  It could be that he’s the voice of reason when you need it.


  1. If you had a dinner party and had to invite a musician, a politician, a famous couple, and only one family member, who would like you ask? Bonus points: What would you be serving, where would you have it, and what would be on your dinner playlist?

Now here’s a chance to make things really interesting and get to know someone. You can go through each category and discuss your favorites. Alternatively, it might not be your favorite, but someone you really want to say something to. This topic should take more than a minute or two. If you go into the venue, maybe you are envisioning the perfect setting for a wedding, too.


  1. What do you like to do when you’re not working?

Other than sleeping. Yes, we all need to sleep, but that answer is about as exciting as, well, sleeping. After your great nap, and you still have a free time, what is the first thing you would normally do?


Best Get to Know You Questions


  1. What’s the number one item you would save from your burning house?

Let’s assume that all your pets and loved ones have already escaped…


  1. What quirks do you have?

Some people are fidgety; others talk to themselves.


  1. What really makes you angry?

Is it a social injustice, or just nail-biting?  As Peter Griffin would say:  What grinds your gears?


  1. What is your favorite thing about your career?

It’s the thing that makes work not feel like work.  It could be the work itself, or it could be the people you work with.


  1. What makes you laugh the most?

Perhaps it is a favorite comedian, or maybe you can’t keep a straight face at snakes with tiny hats.  Letting someone get to know your sense of humor helps them get to know you in a way that nothing else can.


  1. Aside from necessities, what one thing could you not go a day without?

It’s ok to say your phone.  We won’t judge you.


  1. Are you a clean or messy person?

There’s a difference between someone with clutter from actively living in a home and someone who lets the trash overflow until it stinks up the whole house. The first person is messy.  The second one is a slob.


  1. What does a successful relationship look like to you?

Having money and beautiful things is cool and all, but this question is getting at the deeper level stuff like how you two make a life together.


  1. What is something you like to do that other people would probably consider “weird” if they knew?

You don’t have to out your kink.  It can be something mundane like preferring to order your bookshelves by the height of the book.


  1. What was your upbringing like?

Be careful with this one.  Not everyone had a healthy home environment, so be sensitive.


  1. If you had to describe yourself in five words, what would they be?

Hyphenated words count as one word.


  1. What significant life changes have you recently experienced?

Just move to the area?  Start a new job?  Adopt an adorable dog with no discipline and lots of personality?


  1. What is your favorite holiday?

Perhaps you have fond memories of the family at Christmas, or you love dressing up for Halloween.  Some families don’t celebrate certain holidays but observe others, so it can even be an excellent chance to learn about an unfamiliar culture.


  1. What is the first thing you would do if you won the lottery?

Other than pay off all your student loans, of course.


Best Personal Questions


  1. What do you spend most of your time doing?

Other than working and sleeping…


  1. What do you spend way too much money on?

Some folks have an extensive wine collection.  Other people are gearheads or sneakerheads.  Even record collecting can get expensive. On the other hand, maybe fast food and pizza delivery are your guilty pleasure.


  1. How do you calm yourself when you get angry?

Count to 10 or gym therapy?


  1. What was the last time you tried to something to look cool, but it ended in utter embarrassment?

Perhaps you had been playing a lot of Tony Hawk Pro Skater, and I thought, “I can do this in real life.”


  1. What is the most impressive skill you have?

Now’s the time to show off your foreign language skills.


  1. What’s your go-to video or gif for a laugh?

You can pull out your phone and show it off.


  1. Who has impressed you most with what they’ve accomplished?

Did your mom or dad go back and finish college after dropping out years ago?  Was your little sister on Chopped?


  1. What do you hope never changes?

Looks fade, and the world evolves, but certain things like your best personal qualities should never change.


  1. For what in your life do you feel most grateful?

Don’t say your health.  Everyone says that.  Be creative.


Best Deep Questions to Ask


  1. What is the biggest change you want to make in your life?

Quit smoking?  Eat better?  Quit your job and start that business you’ve been dreaming of?


  1. What do you consider to be the highlight of your life?

Were you the first in your family to graduate college?  Maybe it was the birth of your child. Perhaps you accomplished something everyone thought you couldn’t do.


  1. What is your best piece of advice?

It doesn’t necessarily have to be something profound.  Simple but useful advice is excellent too.


  1. What do you think is the best feeling in the world?

It’s ok to get sentimental or sappy here.  That’s a sign that you’re comfortable being         vulnerable, and people do appreciate getting to know the real you.


  1. What is one thing you don’t understand about yourself?

There’s a lot that we don’t understand about ourselves, but being able to admit those         things and work on them shows a lot of character.


  1. What is something beautiful you see every day?

If your partner asks you this question, the correct answer is always, “You.”


  1. What was the single, best realization you have ever had?

We all have moments of clarity, where we realize some kind of existential truth like          money means nothing if you’re miserable, a family is more than just blood relations, and you only get one life so use it all up.


  1. What’s your idea of Heaven?

Lots of cultures have different ideas of the eternal reward for a good life.  What does        yours look like?


Best Hypothetical Questions


  1. Would you rather lose $100, or be given $10 million and have to set it all on fire and watch it burn?

Money’s not everything, and it can’t buy happiness, but neither of these options is             appealing.


  1. Would you rather eat only one meal every three days of whatever you want, and only peanuts in between to keep you alive; or eat whatever you want, whenever, but have no sense of taste?

Some of you will probably be going through a lot of peanuts.


  1. If you had a choice between having a tail or losing a leg, which would you choose?

Tails are good for balance, but you’re going to get some looks.


  1. What would you do if you only had 100 blinks left before losing your vision?

What would you want the last thing you see to be?


  1. If you did not exist, what would you be doing now?

This one can open you for some serious philosophical discussion or get you some very     sarcastic answers.


  1. How would human life be different if crocodiles could fly?

Would you feed crocodiles in the park like pigeons, or would you never leave the house   again?


  1. Can you afford to feed a dinosaur?

You can get into the minutiae of feeding an herbivore as opposed to carnivore.


Best Existential Questions to Ask


  1. To what extent do you shape your own destiny, and how much is down to fate?

Even if you don’t believe in fate, sometimes things happen that are almost too       serendipitous.


  1. Should people care more about doing the right thing, or doing things right?

In other words, would your alignment be chaotic or lawful?


  1. Is a “wrong” act ok if nobody ever knows about it?

This one could lead to an in-depth conversation about morality and law.  For example, is it wrong to break the law if the law itself is wrong?


  1. What do people strive for after enlightenment?

To help others reach enlightenment…or is true enlightenment impossible?  Is         enlightenment the journey or the destination?


  1. If lying is wrong, are white lies ok?

Is it ever acceptable to lie to protect someone’s feelings or to lie when someone does not need to know something?


  1. Can we have happiness without sadness?

According to Lao Tzu, we appreciate happiness more because we understand sadness.


  1. Does sound happen if nothing is present to hear it?

Well, the sound waves still exist, but does observing the event change it at all?


  1. Does observation alter an event?

Speaking of observation, there’s a good reason there are in the existential questions           section.


  1. When you are gone, what would you like people to write for your obituary and why?

How do you want others to remember you?  If you would examine your life, do you think             you’d be right?


Best Questions to Ask Friends


  1. What time of the day do you feel the most energetic and what do you usually do in those moments?

Some folks are night owls.  Others are early risers.  Which one are you, and how do you   make the most of it?


  1. What’s the coolest thing about science?

“It’s true whether you believe it or not.”  ~Neil DeGrasse Tyson


  1. When are you most yourself?

Think about situations where you’re the most vulnerable, where you aren’t worried about             being judged.  That’s probably when you are most yourself.


  1. If you won 100 million dollars, what would you buy first?

Let’s assume that everyone who wins a lot of money is going to pay off debt first.  What are you going to do after that?


  1. What’s the best sound in the world?

Perhaps it’s a sound that brings you comfort and joy, like your child’s laughter.


Best Questions to Ask a Girl


  1. What have you learned from your past relationship?

Whether you learned what you want out of a relationship or what you never want in a       relationship, every past relationship teaches us something.


  1. What is the most important thing that guys should understand about the girl, and it seems to

you that they do not understand?

Please pay close attention to her answer because she is about to give you much insight      into who she is and what she wants.


  1. What is the most useless thing you’ve ever bought?

It could have been an impulse buy, or maybe it was a new gadget that didn’t live up to its             promise.


  1. Which decade do you think had the best sense of style?

Some people love the tailor suits of the 40s, but some are partial to the colors of the 80s.


  1. What is your silliest fear?

Most fears are irrational, but some are more absurd than others.  You never know when    you might have to rescue one another from a vicious moth.


  1. If you had to compare yourself to one fictional character, who would it be?

It’s an excellent chance to find out the kind of people and personal values that she             admires most.


  1. What is the worst pickup line you’ve ever heard?

“You must be a Pikachu because I choose you.”


Best Questions to Ask a Guy


  1. What’s one thing people would never know about you just by looking at you?

You might find out that your shortest friend has a black belt in Judo, or that your fishing buddy is a published poet.


  1. What’s the sweetest thing you’ve ever done for a girl?

Guys sometimes get a bad rep for being insensitive or clueless, but being honest about the times we let our guard down for the women we care about helps break that stereotype.


  1. Have you ever made a decision that changed your entire life? If so, what was it?

Some men have a sudden realization that their daily lives are totally unfulfilling, and they take a significant risk to do something more rewarding.


  1. Would you rather go out or stay in on a Saturday night?

It doesn’t matter if you’re an introvert or extrovert, you could prefer a small gathering of friends or a lively party.


  1. What’s the craziest thing you’ve ever done for a girl?

There are men who’ve driven or flown all the way across the country on a whim to surprise the woman they love.


  1. Where do you like to go to have fun?

A night club, a rock show, a bonfire, a ball game…the possibilities are endless.


  1. What is your favorite thing about being a guy?

Some guys like feeling strong and dependable.  Yes, they like being husbands and fathers. There are lots of things that make being a man great.


  1. What is your most useless skill? Most valuable?

You never know, though.  Some of those skills that we find to be useless sometimes turn out to be very lucrative.


  1. What’s the best bad decision you ever made?

Bad decisions usually make for great stories.


  1. What is the best pizza topping combination?

Feel free to defend the controversial pineapple and ham combination.


Best Questions to Ask Your Girlfriend


  1. What did you always wanted to try but never found the courage to do?

Skydiving?  Or you’re maybe one of the many people who would rather die than speak in public.


  1. Do you enjoy being out in nature?

Ask this before you plan the camping trip.


  1. What’s the best way to spend a rainy afternoon?

Do you go out and try a new restaurant that you’ve been talking about, or do you stay in and just soak up the alone time?


  1. What’s the silliest reason you’ve ever gotten into a fight with someone?

Did you end up in an argument with someone over a sport that you don’t even like?


  1. What slang or trend makes you feel old?

Remember when “lit” only meant to be drunk?  Maybe you’re still using the same slang that you did in the 90s, and someone called you on how often you say “rad.”


  1. How are you really?

Be careful with this one.  Sometimes a “fine” is best left at “fine.”


  1. What was the most thoughtful gift you ever received?

Thoughtful, not expensive. We’re talking about a gift that is priceless because it meant so much.


  1. What’s the best topping/ice cream combination?

Less controversial than pizza topping combination question, but some people are decidedly anti sprinkles.


Best Questions for Couples


  1. What does love look like to you?

Love expressions can look different from person to person.  It’s important to know what love looks like to your partner before you embark on the more major commitments.


  1. What is your favorite dessert?

Hopefully, you both like something different, so you don’t have to share.


  1. When was the first time you became aware of me?

Go ahead and be cheesy with the answer.


  1. Do you remember the first thing we said to one another?

Did it all start with a “hello?”  Or was there that cheesy pick-up line that actually worked?


  1. What’s your favorite memory of me?

It could be funny, cute, or sentimental.


  1. What is your favorite way of spending time with me?

Answering all these questions, of course!


  1. If you were asked to give me a nickname, what would it be?

Ask why.  You want to get the story behind that sappy or silly nickname.  It’ll put a smile on your face.


  1. What’s the one secret you’ve been too embarrassed to tell me?

If you can’t be vulnerable here, it’s going to be really difficult to achieve the vulnerability necessary to make the relationship work long term.


  1. If there’s one thing you’d want to change about me, what is it?

Careful how you answer this one, guys.


  1. If we hadn’t met each other, where would you be right now?

Just say, “alone and sad.”  However, if you feel like you’d be happier otherwise, that might be a sign it is time to part ways.


  1. What would your dream home look like?

Some people prefer that sleek, minimalist, modern look, but others are drawn to the glamour of an old Victorian style.


Best Weird Questions to Ask


  1. What smells make you happy?

For most of us, it’s a smell that evokes a fond memory from childhood.


  1. If you could pick any animal to talk, which would it be?

Cats might turn out to be decent conversationalists.


  1. What’s the most bizarre chewing gum flavor you can come up with?

Who knows, some of the oddball flavors that you come up with might actually exist.


  1. What are the five words that you use the least? The most?

There’s a good chance that the five words you use the least are the five words that you hate the most.


  1. Would you rather be tiny as a fly or massive as a dinosaur?

You could explore a lot of small spaces, being as tiny as a fly, but you might also enjoy stomping around and making noise.


  1. If you were a snake, how long would you want to be?

Some snakes reach double digits in length, and that could be pretty frightening but also a lot of fun.


Best Random Questions to Ask


  1. If you were in a band, what kind of music would you play?

A lot of us used to dream of being rock stars and playing epic solos, but maybe a low-key folk group is more your speed.


  1. If you had to run away from everyone then where would you hide yourself?

Perhaps you would go to a cabin in the woods or mountains, or maybe a private bungalow near a beach.


  1. What do you think is the cleverest animal and why?

Pigs are supposedly very intelligent, but crows have been known to use vending machines and steal from convenience stores.


  1. If you had to be one cartoon character, which would you choose?

A classic character like Bugs Bunny, or do you secretly relate to Bob from Bob’s Burgers?


  1. Would you abandon your phone, internet, family, and friends for three months for a prize of $1 million?

For someone of us, who are used to being connected to a device at all time, this could be harder than it sounds.


  1. What is the word you absolutely hate people for using?

We all have those words that are like nails on a chalkboard for us.


  1. What is the most beautiful thing in nature?

Try not to answer with that Conan the Barbarian speech.  It tends to be a turn-off for         most.


  1. What is your favorite type of candy?

If you’re into seasonal candies, do you make a point to stock up for the year every time the season rolls around?


  1. How do you feel about clowns?

After the new It movie, you can probably guess how most people are going to answer this            one.


Best Interesting Questions


  1. What are you expecting from this relationship?

If you wanted to know exactly where your partner stands, and if you can deliver.


  1. Do loud noises bother you?

Some people have reasons that loud noises bother them more than they bother others.  It’s good to know this so that you can be considerate.


  1. What have you forgotten?

Siri, what is an example of a paradox?


  1. If you had two hours left on earth what would you do?

It might not be long enough to fulfill your lifelong dream, but it’s long enough to go out on a good note.


  1. Who makes you laugh more than anyone?

Is it your favorite standup comic, or does your friend really know how to tell a story?


  1. What’s the best gift you’ve ever given?

Like the question about the most thoughtful gift, it’s not about money.  It’s about how well you know the person and show how you feel about them.


  1. How many times a day do you look in the mirror?

Some folks might be inclined to take the 5th on this, but appearance matters.  Looking good makes you feel good.


  1. If 100 people in your age group were selected randomly, how many do you think they’d find leading a happier life than you?

Again, it’s not always money and possessions that make us happy.


Best Funny Questions to Ask


  1. What product do you think the world could go on without?

And now your friends know what never to get you for your birthday.


  1. If one animal was made the size of a whale, which would be the scariest?

This question is the stuff of nightmares right here.


  1. What is the worst song lyric you have ever heard?

There are song lyrics out there on the opposite side of profound.


  1. What is the craziest thing you’ve seen somebody do at the workplace?

Whether you work in an office or a bar, you’re bound to have some wild stories   eventually.


  1. What is the worst thing your mom caught you doing as a kid?

Even the best-behaved kids manage to find themselves in trouble now and again.


  1. What is that one joke that you cannot tell without laughing hard?

Go ahead and try to tell it.


  1. Who is the most annoying celebrity according to you?

And don’t forget to add why.


  1. What fun activity from your childhood has been completely ruined for kids today?

Some kinds of trouble are a lot harder to get into these days.


Best Fun Questions to Ask


  1. If you were guaranteed the correct answer to one question, what would you ask?

Would you ask about next year’s Super Bowl winner or the meaning of life?


  1. What is an obscure food that you have eaten that most people never tried?

There’s a lot of great, obscure food out there worth trying.


  1. What is your favorite three-word sentence?

Is it a daily affirmation or something more unusual?


  1. If you had to live a week without internet, what will you do to keep yourself busy?

Just think about how much you could accomplish.


  1. What was the most awesome excuse you ever made?

The more epic, yet believable, the better.


  1. What’s the worse topping to put on a pizza?

Here comes the pineapple debate.  At least, you’ll know what not to order when it’s time for a night in for Netflix and chill.


  1. What’s the worst topping to put on ice cream?

And know you know what to buy for a quick, surprise dessert.


  1. What’s a ridiculous thing you’ve ever heard someone say out loud?

Sometimes the overheard out-of-context stuff is some of the best things.


Best Would You Rather Questions


  1. Would you rather go camping in the woods or stay at a beach resort?

The answer to this will help you plan your first or next vacation.


  1. Would you rather be half your height or double your weight?

Some of these have no preferred option.


  1. Would you rather be an ugly genius or a hot moron?

There are perks and drawbacks to both.


  1. Would you rather be itchy or sticky for the rest of your life?

Death is not an option for this one.


  1. Would you rather have the hiccups for the rest of your life, or always feel like you need to sneeze but can’t?

Some of these are just choosing between two forms of torture.


  1. Would you rather eat a gallon of mayonnaise or four sticks of butter?

The breakfast of champions.


  1. Would you rather end the life of a single human being or 500 cute baby animals?

We’re going to guess that most are going to save the baby animals.


  1. Would you rather relive the same day for 365 days or lose a year of your life?

If you’ve seen Groundhog’s Day, you know how infuriating living the same day over and over can be.


  1. Would you rather sell all of your possessions or sell one of your organs?

Some of you might be tempted to bargain if you can choose the organ to lose, knowing     that the appendix is an organ.


  1. Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?

If your life about to become an endless night club or karaoke night?


Best This or That Questions


  1. Burgers or pizza?

Seriously though, aren’t pizzas basically open face burgers? These are both delicious options so either way is great. If she says salad on the other hand…


  1. Money or fame?

Would you take the money and buy the fame? That’s a good choice probably. Remember             though, money can buy mostly everything except for happiness.


  1. Too warm or too cold?

Just keep in mind that you can always put on more clothes, but you can only strip down    so far. Maybe that is a bonus for you though, so it is definitely too warm! Bring out the    palm trees and beach and save the cold arctic for someone else.


  1. Pepsi or Coke?

We’re talking about Coca Cola here, not the Texas Coke, which could be any soft drink. If this is a silly question, the real one is actually Mt. Dew or Monster.


  1. Beard or mustache?

Or neither?  It’s still ok to rock the clean shaven look. This always goes for the guy, not   the girl. Just saying.


  1. Popcorn or chocolate?

Picture it: you are at the movies. Do you go for the salty bucket of popcorn or a sweet       taste of candy? The choice is yours and yours alone… until you feel that extra hand in       your popcorn.


  1. Classic or modern?

Or does it depend upon what you’re talking about – cars, houses, apparel, artwork? You   will most likely still gravitate to either an old-fashioned style or innovative one either           way.


  1. Smile or eyes?

Which one is the better window into someone’s personality? Teeth can be a deal breaker, maybe, but invisible retainers are on the rise!


  1. Fast food or mom’s cooking?

Though sometimes, there’s not much of a difference. If you were a frozen pizza and          cereal kind of kid, you might need a new idea of what home cooking really means.      Basically, would you rather eat fries or mashed potatoes?


  1. Batman or Superman?

And why? Maybe you are more into the Avengers, X-Men, or some other superhero         team. Plead your case.


  1. Call or text?

Some people just prefer to type things out. That doesn’t mean they are impersonal. After all, a poem can have one beautiful line while a podcast might expose a thousand hateful          words.


  1. Plane or train?

Some people hate the hassle of airports, but riding in the car can cause anxiety. All           aboard!


  1. Sweater or hoodie?

And if you have a favorite hoodie (because serious, who picks sweater?), get ready to     give it to your girl.


Best Truth or Dare Questions


  1. After you’ve dropped a piece of food, what’s the longest time you’ve left it on the ground and then ate it?

Basically, do you believe in the 5-second rule? Did those seconds turn into minutes?


  1. What was the last thing you searched for on your phone?

Be honest. You probably aren’t alone with your Googling needs.


  1. How would you rate your looks on a scale of 1 to 10?

We tend to be hardest on ourselves. However, being a little too insecure can be a turn-off so try your best to be honest while remaining unbiased. Discuss what parts of your      appearance you like and what ones you aren’t that excited about… thanks mom and dad.


  1. What’s the most unflattering school picture of you?

By the time we get to middle school, most of us have some very unflattering school          photos. Did you go through that ugly phase? Maybe it was more recently when a          frienemy took an unflattering photo of you at the worst angle possible and posted online.


  1. Would you wear your shirt inside out for a whole day if someone paid you $100?

It would be an easy $100 depending on the shirt. What other things would you do for        money? They say everyone has a price.


  1. How did you get an embarrassing nickname?

It might be from your grandma or a childhood bully. Maybe you actually adore your nickname. Either way, it’s time to spill the beans.


  1. Dare: Give someone your phone and let them send one text to anyone in your contacts.

Now this is a huge test of trust. This dare could be dangerous no matter who you are. You            could really learn if that person has revenge out for you. Likewise, you will see firsthand            how that person feels about pranks.


  1. Dare: Stand up and sing your favorite song.

Sure, this dare might seem easy if you are a professional, but even Adele gets stage fright and she has a Grammy. If you are in a public place, it will probably be awkward, but funny. Heck, even if you two are home, this might be dreadfully unpleasant. Show you aren’t afraid to take a challenge and use your back up karaoke song. Wait, you don’t have a go-to song yet?


  1. Dare: Let someone use permanent marker to draw or write something on your hand.

At least you didn’t let them draw on your face!


  1. Dare: Take an unflattering picture and post it online.

Ok, back to the ugly pictures of yourself. Let’s face it; we live in a visual world and people care a lot about their appearance. Talking about and old picture when you had glasses and braces is not the same as posting a current snapshot of a double chin. How much confidence do you have in yourself and your friends to see the real you?


  1. Dare: Read your last text message out loud.

If it was something silly with autocorrect, you can all have a good laugh. Maybe the message was meant to be private because it is hurtful. Did your feelings just get hurt?



Best What If Questions


  1. What if computers took over the world?

There is an entire genre of fiction about why this is bad. Maybe now is the time to discuss            your theories whether they are based off of the latest novels, movies, or comics.


  1. What if someone wrote a story about you? Would you be considered a hero or a villain in your story?

Or maybe you might be the anti-hero. Alternatively, your story might not require any       saving.


  1. What if we found live dinosaurs living on a remote island?

It’s the plot of almost every Jurassic Park sequel.


  1. What if you could change one thing about the world? What would it be?

Would you end war and hunger, or would you do something simpler?


  1. What if you woke up and discovered you were the only person on earth?

You can least celebrate the end of rent and bills, right? Maybe you will learn about the     person’s sarcasm and sadistic humor along the way.


  1. What if you were offered the opportunity to go into space?

Even if you don’t like flying, it would be hard to pass up a trip to space. Just imagine the things you would see out there.


  1. What if you could marry someone famous, either living or dead?

An interesting way to find out what traits a person finds attractive. Take a minute to think what really makes marriage material in your mind. Or would you just pick the hottest person to ever live?


  1. What if you could start your life all over? What would you do differently?

Imagine you get to take all the wisdom and knowledge you have now with you. You         would probably make different decisions here and there, even if you wanted the outcome             to be mostly the same in the end.


  1. What if you could have a superpower for one day? What would it be and why?

It would be tricky to decide between super strength and the ability to fly. Maybe you would rather be invisible or be able to read minds. There are so many theoretical options to discuss that you might as well assume the sky is the limit.


  1. What if you were unable to talk or walk for 24 hours?

Not only does this question make you consider your privileges, but it also sets the tone for those who do not have these seemingly basic capabilities that we take for granted. Maybe you will stop be lazy and be grateful for what you can do yourself. Or you would just ring a bell and draw a picture.


  1. What if you had triplets?

Ok, this fun question is not too crazy to think about after all. Many families have twins, triplets, and even quadruplets. However, beyond the thought of matching outfits, what if you really did have multiples? It would most likely change your entire lifestyle and outlook on life.


  1. What if you could snap your fingers and transport to a different place?

That would be awesome assuming you could do it safely. The real question is: where would you go first? The world is a big place with fascinating regions. Does the future or past count as a different place?


  1. What if you could see into the future but you couldn’t tell anyone?

Would it be worth it to have this amazing knowledge, but nobody to share it with? As long as you can play the lottery and get away with it then it’s all good.



Best Most Likely To Questions


  1. Who is most likely to give all their money to charity?

This question is about who has the bigger heart, or who is the biggest sucker for a sob       story?


  1. Who is most likely always to be happy?

Is it a positive mental attitude or just a generally happy-go-lucky attitude?


  1. Who is most likely to have weird phobias?

Trypophobia is not technically a phobia, but most everyone feels disgusted at tiny holes too close together.


  1. Who is most likely to get in a fight?

Which one of you is the scraper and not afraid to go there? The idea of fighting might be a turn-off, but what if she is looking for a protector? Choose your words wisely. A fight         doesn’t always have to mean physically, either.


  1. Who is most likely to be the first one to die in a zombie apocalypse?

Would it be a selfless sacrifice, or would it be a total blunder?


  1. Who is most likely to invent something useful?

Which one of you is the more resourceful one? It’s refreshing to hear someone being logical and practical with everyday needs.


  1. Who is most likely not to take a shower for a week?

Hopefully, neither of you are cool with going a week without a shower, but you have to   pick one.


  1. Who is most likely to take longer to get ready?

It takes a lot of hard work to look effortlessly cool. This question dives into the category of bathroom prep. Hair, makeup, and nails – oh my! On the other hand, man grooming and wardrobe options can take just as long.


  1. Who is most likely going to kill the spider?

Alternatively, will one of you scoop the spider up and take it outside? Maybe it depends on the size and its level of radioactivity.


  1. Who is most likely the best dancer?

A trip to the club can settle this one. Whether it is fast or slow, dancing is a great way to exercise and be close to one another.


  1. Who is most likely to get a hangover?

Here is your chance to learn about who can hold their liquor and who likes to praise the porcelain throne. If you aren’t into a sloppy drunk, take note that maybe this behavior should be addressed and changed.


  1. Who is most likely to apologize after an argument?

Get ready to learn about who is the real peacemaker. Sometimes it is not about being        right, but most of the time it is.


  1. Who is most likely to go to church on Sunday?

Maybe both of you, maybe neither; however, the rule for these fun questions is that you    have to pick one of you as the most likely.


  1. Who is most likely to take out the garbage?

The male assuming so should take on this role, but in an era of equality, the results might surprise you. Are you open to the idea of shared chores even if it means a guy doing the vacuuming? Things to think about…


  1. Who is most likely to plan a date night?

This question can reveal who is more romantic, organized, and willing to take the time and effort to show how much you care.


  1. Who is most likely to bring a pet home?

Are you a sucker for a rescued puppy or lost kitten? Maybe pets aren’t your idea of a good surprise. This idea is good to know before you move in with someone.


  1. Who is most likely the night owl?

Or the early bird? Maybe you both are more like exhausted pigeons who perform best for about an hour in the afternoon. There’s nothing wrong with that!


  1. Who is most likely to ask for directions?

Sure, we live in a technological era full of GPS. The chances of actually needed to stop for directions might perplex you at first, but what if your phone is dead? Maybe the satellite system for your car navigation went down. Besides, what this fun most likely question is really hinting to is who is willing to ask for help when you truly need it?


  1. Who is most likely to fall asleep during the movie?

After learning about what types of movies your partner likes, this question is always fun to ask. Even if she did get to pick the film for the night, will she fall asleep within the first 15 minutes?


  1. Who is most likely to bring up marriage first?

Maybe you want to leave this most likely question for a little later in the relationship. However, some people know right away when they found that special someone. A better way to look at this fun question is to actually ask it at your wedding. After discovering the love of your life, consider playing the most likely game during your reception. How? The bride and groom sit in chairs with their backs touching and take off their shoes. The groom holds one of his shoes and one of her shoes; likewise, for the bride.

The emcee will ask most likely questions. Using the shoes, the future spouses will hold up who they think is most likely to do that question. If the shoes match, they get a point, but if not, maybe they should have discussed some of these things! It can be a really sweet yet silly game for everyone involved. Google the shoe game for weddings and you can see how the entire thing plays out.



How to Start a Conversation: 5 Simple Steps


For the more introverted types, striking up a conversation can seem daunting, but don’t despair.

We’ve got these five tips for getting a conversation going with whoever is around you.


1: Get a feel for where you are

Before you start a conversation, analyze the situation. Some settings aren’t the right place for specific conversations.  You wouldn’t ask the guy from the cubicle over about the meaning of life over your lunch break.  Similarly, there are things you wouldn’t ask on a first date.  Think about where you are and who you’re with before you jump into the topic. After all, your goal is to get to know the person, not offend them.


2: Relax

Yeah, it can be hard to be cool in a situation that is different or new. On top of that, you normally would find that chatting with people can be awkward for you in the first place. You don’t want to just blurt out one of these questions randomly to a brand new acquaintance.  However, you can pay attention to the conversation and use clues to help you figure out what to ask.  When someone says where they work, that’s usually a good segway to ask about career goals or educational backgrounds.

By no means do you need to be the center of attention or trail along every single word. Take a deep breath, go out there, and listen. Then get in where you fit in the conversation and say something that relates to the topic but is equally interesting.


3: Keep an eye on body language

Don’t force the conversation.  If someone looks like they want to get away, let them.  Maybe they look at their watch or around the room. Perhaps the folder their arms or turn their body away from you.

If you can’t pick up so easily on those hints, listen for when the person says s/he should be going or has somewhere to be. If you are in the middle of making a point, or getting to the punch line, that is your cue to wrap it up. You don’t have to drop the conversation abruptly, but be respectful of the person’s time and need to leave. It is easy to end a conversation simply by saying, “Hey, it was good chatting; I’ll see you around.”  Then move on, and don’t take it personally.


4: Participate

Listening to the other person talk is essential. However, you’ve got to be active in the conversation for it to go anywhere. Asking a laundry list of questions seems like an interrogation. Instead, take turns asking questions about each other; that means you must be prepared to participate on your end, too.

Participation also relates to focus. Don’t ask a question and then go digging in your phone or gazing around the room.  Make eye contact and react to what the other person is saying.  Some of us are fidgety or have attention disorders, and that’s ok.  If you do, make sure you have a way to help focus your attention.


5: It’s ok for a conversation to end

All discussions have to stop at some point, even if you haven’t said all that you wanted.  You can usually feel when this is happening. Like with the body language, maybe a host starts to move towards the door, or you hit a long lull in the conversation.  Whatever happens, take the hint, parts ways well, and move on to what’s next.  As much as people appreciate a good conversationalist, they also enjoy someone who doesn’t overstay a welcome. If you are trying to build a new relationship, sometimes having a great conversation and leaving some room for more discussion later is a wonderful way to end the date.

Striking up a conversation with someone doesn’t have to be nerve wrecking when you already have topics to discuss. Feel free to use this ultimate question list whether you are planning your first date, preparing for a business meeting, or hanging out with a new group of friends. You might even surprise yourself by analyzing the questions alone just to become more familiar with yourself.