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Have you ever found yourself in a conversation that’s as flat as a pancake? There’s an awkward silence and no one has any idea what to say next. Don’t worry, for we’ll give you the perfect remedy with this list of deep questions to ask someone.
If you often find yourself in the same old “How’s the weather?” or “Did you catch the game last night?” routine, then it’s time to shake up your conversation game.
You see, small talk is passé. If you want to build a relationship with someone, you need to connect on a deeper level. So whether you’re trying to break the ice with a new person or just curious to know about your co-workers beyond their favorite lunch spot, these questions to ask will be your trusty companions!
These questions to get to know someone will help you discover their personality, thoughts, and feelings. It’s like a quest to uncover the mysteries of their mind.
First things first: forget the predictable “How are you?” and “What’s up?” questions. Instead, get creative and ask something unexpected. Try icebreakers like “If you were a superhero, what would be your superpower?” or “What’s your spirit animal?”
But remember this golden rule: be genuinely interested. Listen attentively and show curiosity. Nod, smile, and let out a “No way!” or “That’s amazing!” from time to time in the conversation. Remember, it’s not an interview, so don’t monopolize the conversation. The right body language is important too.
With these 142 thought-provoking gems, you’ll be able to turn awkward conversations into heart-to-heart discussions.
This post may include affiliate links.
#1
If when you died, you got put into a room for eternity with people who died the same way, how would you want to die?
Squirrelly Panda 2 years ago
In my sleep. Still a peaceful way to go and there would be a very wide range of people from all walks of life.
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#2
If you could share a meal with any 4 individuals, living or dead, who would they be?
#4
When have you felt your biggest adrenaline rush?
#5
What are the two biggest lessons you’ve learned from previous relationships?
Lousha 2 years ago
If it feels off, it is off, don't waste time trying to convince yourself it's all in your head. And don't regret the s*** relationships. They brought you one step closer to the one that will be the right one, and by then you'll have enough experience to appreciate how good it is.
#6
If a genie granted you 3 wishes right now, what would you wish for?
#7
If you could choose to do anything for a day, what would it be?
#9
What would you do if one day you woke up and every person was just gone without a trace?
#13
What are you most grateful for?
#14
What’s something horrible that we as humans have accepted, because that’s just how things are; but actually things don’t have to be that way at all?
#15
If everything was quantified, what life stats would like to see for yourself?
#16
What options would come up if you could “right-click” people?
#18
What really makes you angry?
#19
What is your biggest complaint about your job?
Headless Roach 2 years ago
Having to wake up in the morning. Other than that, I enjoy what I do
#21
What makes you laugh the most?
Headless Roach 2 years ago
It’s easier to list what doesn’t. I’m the kind of person who will laugh at cheese looking weird.
#25
Are you more into looks or brains?
#27
What’s your philosophy in life?
#28
What do you wish you could re-live in your lifetime?
#29
What do you wish you had more time for?
#31
What’s the best conspiracy theory you can make up on the spot?
#32
What’s something you wish you had never learned how it was made or how it works?
#33
What do most people overestimate or underestimate about you?
#34
You have unlimited wishes but every time you make a wish what you love most is erased from the world. How many wishes do you make and what do you wish for? (No, you can’t wish not to have things erased from the world.)
#37
What is your biggest fear?
#38
Have you ever had a nickname? What is it?
#39
What is your proudest accomplishment?
#42
If you could go back in time, what year would you travel to?
#43
List two pet peeves. Aside from necessities, what one thing could you not go a day without?
#45
Do you consider yourself an introvert or an extrovert?
#49
What is the craziest thing you’ve ever done and would you do it again?
#50
What’s the one thing you would like to change about yourself?
#51
If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?
#53
What is your idea of a perfect vacation?
#54
When was the last time you broke someone’s heart?
#56
What kind of parent do you think you will be?
#57
Do you judge a book by its cover?
#59
Are you religious or spiritual?
#61
What’s been your biggest mistake so far in life and what did you learn from it?
#63
What’s your favorite book/movie of all time and why did it speak to you so much?
#65
What’s something you learned recently that you really should have already known?
#67
What piece of culture or trend has died out, but you would like to see it make a comeback?
Headless Roach 2 years ago
Not that it died completely, but certain music of the 80s still rocks my boat
#69
What’s something weird that you recommend everyone trying at least once?
#76
If colors had a taste, what would each color taste like?
#77
What names were ruined for you because you knew someone terrible with that name?
#78
What would an amusement park filled with your biggest fears be like? What rides would it have?
#80
If you could switch genders for a length of time of your choosing, would you? And if so, how long?
#81
What silly thing do you take a lot of pride in?
#84
What is the strongest animal you could win against with just your bare hands and feet?
#86
What is something you probably should do, but will never do?
Bored Retsuko 2 years ago
I have a couple of medical surgeries pending that I've been postponing for years...
#93
Who would you want to be stranded with on a deserted island?
#94
What did you want to be when you were small?
Rose the Cook 2 years ago
An archaeologist but being from a poor family made university out of the question. Had to settle for a trade with a paid apprenticeship then pay my own way through something more practical, employment wise, as an adult. Always wish I had been able to have my first choice though.,
#98
How would you describe your best friend?
#110
What was something you ate regularly as a child but now cringe at the thought of eating?
#112
If you were given $15,000 to give the most amount of happiness to the most amount of people, what would you do?
#113
What’s an innocent mistake you made that had dramatic consequences?
#114
If you could hear every time someone said something good about you or something negative about you, which would you choose?
#115
What do you think people automatically assume about you when they look at you?
#119
When was the last time you had a gut feeling about something that turned out to be correct? How about a time your gut feeling was wrong?
#120
How decisive or indecisive are you?
#121
If you could dedicate your life to solving one problem, what problem would you choose?
#126
What’s the most stress relieving thing you can get/do for less than 20$?
#129
If you could change your first name, what would be the most epic name you could choose?
#130
If you were given immortality, but there was one condition, what would stop you from accepting immortality?
#135
Who is your favorite author?
#138
How often do you go into a room and forget why you went into the room?
#140
What’s an ideal weekend for you?
#141
Have you ever faked happiness?
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