Fun Questions
There are A LOT of question lists out there. Trust us, we’ve looked at almost all of them.
But fear not! We did all of the hard work for you. What you’re about to dive into is the ultimate compilation of fun questions, gathered from all corners of the world / cyberverse. The purpose of this list is to make you and your friend laugh, debate, and connect over a list of questions ranging from your childhood preferences to your thoughts on conspiracy theories.
This list is built specifically for close families and friends…and complete strangers. In short, we hope everyone who stumbles across our happy little corner of the internet leaves with a list of absurd, spicy, and equal parts meaningful and meaningless questions that you can reference in conversation again and again.
And, as always, we extend to you a warm Chatterbox invitation to upvote your favorite questions!
- What is an embarrassing nickname you’ve been calling your partner or best friend lately?
- Would you rather win a $10 million lottery today or be promised that you would make $10 million yearly in the career of your choosing but know that it would take time?
- What is the most trivial thing about which you have a strong opinion?
- If you woke up in the body of someone of the opposite gender, what would you be interested to find out or do?
- What is your favorite activity that doesn’t cost any money?
- How PDA are you in a relationship on a scale of 1-10?
- If you could only keep three apps on your phone which would you keep? (Pre-loaded apps like Messages / FaceTime / calendars do not count towards your three).
- How much would someone have to pay you to be on the bachelor / the bachelorette?
- What rule did you argue over most with your parents?
- How many texts did you send your partner or best friend today?
- Are you hiding anything in your room?
- What is something you really resent having to pay for?
- What is your hottest take about the differences between men and women?
- Of all your friends, who is suffering from the dumbest problem?
- How good of a dancer are you on a scale of 1-10?
- Do you have an above or below average memory?
- What is your favorite commercial?
- You have $10m USD but you can only buy things that start with the first letter of your name. What do you buy?
- Would you rather have the ability to see ten minutes in the future or 150 years in the future?
- What is your best trivia category?
- If you had to pick three people to do a cross-country road trip with today who would you choose?
- In heaven, everyone gets unlimited ______.
- What trend made you feel old for the first time?
- What conspiracy theory is easiest for you to defend?
- If you could magically make one food or habit healthy, what would you choose?
- Which of your friends would you most want to be your manager? Which of your friends would you least want to be your manager?
- Which swear word do you use the most?
- Who is your favorite of your exes?
- What is less expensive than it should be? What is more expensive than it should be?
- What is your favorite article of clothing that you own?
- What moment from your upbringing would you pick for the opening cameo in a biopic about you?
- If you could be a part of any TV family which would you choose?
- Which Winter (or Summer) Olympics event do you think you’d have the best chance at competing in?
- What do you think you do better than 90% of people?
- What was most different about your life one year ago?
- Of everyone in the group with you right now, who would you choose to be your parent, sibling, child, and in-law?
- What do you get the most compliments about?
- What is your favorite chore?
- In a “Freaky Friday” situation where you woke up in someone else’s body, who would you like to be for a day and have them inhabit your body?
- Do you think you are an above or below average dancer? Do you think you are an above or below average singer?
- What kind of shower-er are you?
- What is one thing that instantly makes your day better?
- Do you think you would perform better than average or worse than average in the Hunger Games?
- Which of your friends would you be most likely to follow if they started a cult?
- What is your least popular or most controversial opinion?
- What scientific or technological advance blows your mind? Is there any technology that seems so futuristic and advanced you’re surprised it actually exists?
- If you could change your name (first, last, middle, or any combination of the three), what would you change it to and why?
- If you could develop any one career skill overnight what would it be?
- Would you rather spend a month in Hawaii, Paris, New York, or London?
- Target: Underrated or overrated?
- If you could own one professional sports team which would it be?
- Do you think your music taste matches your personality? Why or why not?
- Who would you be willing to pay the most to see in concert?
- Which celebrity do you think you would have the best chance of actually winning over romantically?
- Which fictitious world would you most like to live in?
- Say your first impression of everyone in the room.
- What is the pettiest thing you have done?
- If you were to be reincarnated, what do you think you would come back as?
- How do you waste time?
- What was your most interesting Google search or internet rabbit hole that you went down this week?
- How much would someone have to pay you to use a flip phone for the rest of your life?
- What food/drink are you convinced people are pretending to like?
- What was your first kiss like?
- How old were you when you learned Santa wasn’t real? How did you find out?
- What is the best Halloween costume you ever wore?
- What game show or reality TV show would you create?
- What trend did you participate in high school you’re most embarrassed by now?
- Which family member is the best cook? Stack rank if applicable.
- What percentage of your co-workers or peers do you get along with?
- What board game (or game generally) are you the worst at?
- How many pairs of shoes is too many to own? At what point does it become excessive?
- If you could have one mystery solved which would you choose?
- Have you ever been told that you have a doppelgänger? If so, who is it?
- If you could snap your fingers and everyone would call you by a nickname, what would it be?
- What are you bored of?
- What are you convinced people are pretending to enjoy?
- What habit / routine are you most proud of?
- What would you do with your extra time if you didn’t have to sleep?
- What was the most difficult conversation you ever had?
- What was your most embarrassing recent google search?
- What instance of FOMO stands out most in your life?
- Where would your horcruxes be hidden?
- What was your most memorable sunset?
- What do you think will be the most cringey about our society or yourself as an individual 100 years from now?
- Do you have a favorite quote?
- How long does it take you to get ready in the morning?
- If you knew you had to present today, what would you feel most comfortable giving a TedTalk about?
- What is the strangest coincidence that ever happened to you?
- What is your favorite random fact?
- What is the strangest food combination you enjoy?
- How do you waste time most often?
- What is the worst outfit you ever wore?
- What is your favorite way to spend a day off?
- What is the phone app you use most?
- Generally speaking, do you think your dreams have meaning?
- Assume you have a lot of musical talent. If you started a band, how many people would be in it and which position would you be? What would you name it? What genre would you play?
- What would you rate your penmanship out of 10?
- If seasons never changed, which would you most like to live in eternally?
- If you could go back and relive one day in your life without changing anything about it, which day would you revisit?
- What would be the title of your memoir?
- What is the first thing you do in the morning?
- Do you wash your legs in the shower?
- Are you superstitious about anything?
- Do you have any recurring dreams?
- What does your fridge typically look like?
- What do you consider to be the ultimate guilty pleasure?
- When’s the last time you felt like a third wheel?
- What was the last cookie you ate?
- How much time do you spend in front of the mirror on an average day?
- Is there anything on your calendar that you’re dreading?
- When was the last time you blushed?
- When was the last time you set off the fire alarm?
- If you were an inanimate object, what would you be and why?
- If you could be any mythical creature, what would you be and why?
- Some historical figures have epithets attached to their names, like The Mad or The Wise. What would you like yours to be?
- If you were a character in a movie, book, or television show, what genre would you live in?
- What is your favorite word and why?
- What is the most ordinary-seeming thing that you find fascinating?
- Have you ever met one of your heroes?
- How many times have you gotten pulled over? Do you try to talk your way out of tickets?
- What do you know isn’t real, but want badly for it to exist?
- What are your unfiltered thoughts on Taylor Swift?
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