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.
#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?
#2
If you could share a meal with any 4 individuals, living or dead, who would they be?
#3
What was the worst phase in your life?
#4
When have you felt your biggest adrenaline rush?
#5
What are the two biggest lessons you’ve learned from previous relationships?
#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?
#8
What would you do if your parents didn’t like your partner?
#9
What would you do if one day you woke up and every person was just gone without a trace?
#10
Who is your hero?
#11
Is what you’re doing now what you always wanted to do growing up?
#12
What do you most look forward to about getting old?
#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?
#17
What motivates you to work hard?
#18
What really makes you angry?
#19
What is your biggest complaint about your job?
#20
Would you rather win the lottery or work at the perfect job? And why?
#21
What makes you laugh the most?
#22
If you could go back in time to change one thing, what would it be?
#23
If you were a superhero, what powers would you have?
#24
What are you most thankful for?
#25
Are you more into looks or brains?
#26
Have you ever lost someone close to you?
#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?
#30
How often is your brain on autopilot?
#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.)
#35
What’s the most spontaneous thing you’ve done lately?
#36
What is your family member’s proudest accomplishment?
#37
What is your biggest fear?
#38
Have you ever had a nickname? What is it?
#39
What is your proudest accomplishment?
#40
What’s the longest you’ve gone without sleep (and why)?
#41
Where do you see yourself in five years?
#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?
#44
How would your friends describe you?
#45
Do you consider yourself an introvert or an extrovert?
#46
Which parent are you closer to and why?
#47
What do you think of best friends of the opposite gender?
#48
What was the best phase in your life?
#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?
#52
What’s the one thing that people always misunderstand about you?
#53
What is your idea of a perfect vacation?
#54
When was the last time you broke someone’s heart?
#55
Would you relocate for love?
#56
What kind of parent do you think you will be?
#57
Do you judge a book by its cover?
#58
Who is that one person you can talk to about just anything?
#59
Are you religious or spiritual?
#60
Would you take on your significant other’s religion if they had one?
#61
What’s been your biggest mistake so far in life and what did you learn from it?
#62
What did your past relationship teach you?
#63
What’s your favorite book/movie of all time and why did it speak to you so much?
#64
What’s the best piece of advice someone has given you?
#65
What’s something you learned recently that you really should have already known?
#66
Is flirting cheating?
#67
What piece of culture or trend has died out, but you would like to see it make a comeback?
#68
What kinds of things are normal now but will be highly valued antiques a century later?
#69
What’s something weird that you recommend everyone trying at least once?
#70
What do you really wish you knew when you were younger?
#71
Who do you make happy?
#72
What was the worst phase you went through in life?
#73
What unnecessary products or services do you consider necessary?
#74
Which fictional villain made you feel real hatred towards them?
#75
What habit do you have that you think not many other people have?
#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?
#79
What do people really need to chill out about?
#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?
#82
How would the world change if health potions existed?
#83
What would be the absolute perfect day?
#84
What is the strongest animal you could win against with just your bare hands and feet?
#85
What event from the past do you most want to see a recording of?
#86
What is something you probably should do, but will never do?
#87
What great idea would you like to try if you had enough money?
#88
Do you like or dislike surprises? Why or why not?
#89
What is your favorite book to read?
#90
What are your hobbies?
#91
If you could choose to do anything for a day, what would it be?
#92
What is your favorite family vacation?
#93
Who would you want to be stranded with on a deserted island?
#94
What did you want to be when you were small?
#95
If money was no object, what would you do all day?
#96
What is the worst gift you have received?
#97
What’s on your bucket list this year?
#98
How would you describe your best friend?
#99
What qualities do you admire about your parents?
#100
Does your job make you happy?
#101
Would you ever take back someone who cheated?
#102
What is a relationship deal breaker for you?
#103
When do you think a person is ready for marriage?
#104
What’s your biggest regret in life?
#105
Do you believe in second chances?
#106
Where is your favorite place in the entire world to go?
#107
Why did your last relationship end?
#108
Are you confrontational?
#109
What’s your “and then it got worse” story?
#110
What was something you ate regularly as a child but now cringe at the thought of eating?
#111
What’s the craziest thing you’ve ever done for love?
#112
If you were given $15,000 to give the most amount of happiness to the most amount of people, what would you do?
#113
What’s an innocent mistake you made that had dramatic consequences?
#114
If you could hear every time someone said something good about you or something negative about you, which would you choose?
#115
What do you think people automatically assume about you when they look at you?
#116
Looking back on your life, what have you done that has given you the most satisfaction?
#117
What’s the best gag gift you’ve ever seen or gotten?
#118
What’s your story?
#119
When was the last time you had a gut feeling about something that turned out to be correct? How about a time your gut feeling was wrong?
#120
How decisive or indecisive are you?
#121
If you could dedicate your life to solving one problem, what problem would you choose?
#122
How often do you feel utterly worn down?
#123
What was the best thing about how your parents raised you?
#124
If jobs/careers had slogans what would be some of their slogans?
#125
Why do you think we dream?
#126
What’s the most stress relieving thing you can get/do for less than 20$?
#127
How do you feel about God?
#128
What scrambles your brain every time you think about it?
#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?
#131
What would you change about yourself if you could?
#132
What is your favorite thing about your career?
#133
What is the best gift you have been given?
#134
If you could only eat one meal for the rest of your life, what would it be?
#135
Who is your favorite author?
#136
What is your ideal meal?
#137
What’s the biggest lie that a guy has told you?
#138
How often do you go into a room and forget why you went into the room?
#139
What did you want to be when you were younger?
#140
What’s an ideal weekend for you?
#141
Have you ever faked happiness?
#142
What are your highest aspirations?
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