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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.

#1

Deep Questions To Ask Someone To Know Them Better 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?

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Squirrelly Panda
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

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?

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#3

What was the worst phase in your life?

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#4

Deep Questions To Ask Someone To Know Them Better When have you felt your biggest adrenaline rush?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Spinning circles on an icy highway in the middle of the night watching oncoming traffic come at me. All I could think is, well this is it, this is how I die. I hope someone remembers I own animals and goes to feed them.

#5

What are the two biggest lessons you’ve learned from previous relationships?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

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.

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#6

If a genie granted you 3 wishes right now, what would you wish for?

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#7

Deep Questions To Ask Someone To Know Them Better If you could choose to do anything for a day, what would it be?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Get my old cat back to life so I can tell her again how much I love and miss her.

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#8

What would you do if your parents didn’t like your partner?

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#9

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

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#10

Deep Questions To Ask Someone To Know Them Better Who is your hero?

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#11

Is what you’re doing now what you always wanted to do growing up?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I wanted to be happy. I was attracted to different professions at different times but what I always really wanted is a happy life. So yes, it is.

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#12

What do you most look forward to about getting old?

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#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?

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#15

If everything was quantified, what life stats would like to see for yourself?

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#17

What motivates you to work hard?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Intellectual engagement. If I'm not interested, I can't put too much effort in, even if it would be really rewarding financially or otherwise.

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#19

Deep Questions To Ask Someone To Know Them Better What is your biggest complaint about your job?

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Headless Roach
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Having to wake up in the morning. Other than that, I enjoy what I do

#20

Would you rather win the lottery or work at the perfect job? And why?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Perfect job. I like getting things done. On the other hand, I could support more charities or influence policy changes if I had money.

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#21

What makes you laugh the most?

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Headless Roach
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

It’s easier to list what doesn’t. I’m the kind of person who will laugh at cheese looking weird.

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#22

Deep Questions To Ask Someone To Know Them Better If you could go back in time to change one thing, what would it be?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Neandertals outbreeding homosapiens. I'd like to see what the world would be like if the scales had tipped the Neandertals way.

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#23

If you were a superhero, what powers would you have?

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#24

What are you most thankful for?

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#25

Deep Questions To Ask Someone To Know Them Better Are you more into looks or brains?

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#26

Have you ever lost someone close to you?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

So very many. Cousin, grandma, mom, neighbor (substitute grandma) ,dad, Uncle, uncle, uncle, uncle, cousin, friend, friend

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#27

What’s your philosophy in life?

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#30

How often is your brain on autopilot?

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#31

Deep Questions To Ask Someone To Know Them Better What’s the best conspiracy theory you can make up on the spot?

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Erin Ward
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

The moon is a sentient being and it's watching us like the Jerry Springer show

#32

What’s something you wish you had never learned how it was made or how it works?

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#33

What do most people overestimate or underestimate about you?

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#34

Deep Questions To Ask Someone To Know Them Better 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.)

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#35

What’s the most spontaneous thing you’ve done lately?

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#36

What is your family member’s proudest accomplishment?

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#38

Have you ever had a nickname? What is it?

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#40

Deep Questions To Ask Someone To Know Them Better What's the longest you've gone without sleep (and why)?

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Erin Ward
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

3 days, I was in a war zone and working in the operating room while in the army

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#41

Where do you see yourself in five years?

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#42

If you could go back in time, what year would you travel to?

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#43

Deep Questions To Ask Someone To Know Them Better List two pet peeves. Aside from necessities, what one thing could you not go a day without?

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#44

How would your friends describe you?

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#45

Do you consider yourself an introvert or an extrovert?

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#46

Deep Questions To Ask Someone To Know Them Better Which parent are you closer to and why?

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#47

What do you think of best friends of the opposite gender?

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#49

Deep Questions To Ask Someone To Know Them Better What is the craziest thing you’ve ever done and would you do it again?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Yes. If everyone else is doing the same thing, it is well-covered territory. Might as well do something crazy.

#50

What’s the one thing you would like to change about yourself?

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#51

If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

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#52

Deep Questions To Ask Someone To Know Them Better What’s the one thing that people always misunderstand about you?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That being blunt and matter of fact is not the same as being rude.

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#53

What is your idea of a perfect vacation?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Everyone else going on vacation so I can enjoy my home without anyone visiting, calling or interacting with me and my partner at all.

#54

When was the last time you broke someone’s heart?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Wouldn't think I ever did. Upset, cause some temporary sadness, sure.

#55

Deep Questions To Ask Someone To Know Them Better Would you relocate for love?

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Jj321
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Yes, if I had too, but my husband respects that I don't want too.

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#58

Deep Questions To Ask Someone To Know Them Better Who is that one person you can talk to about just anything?

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#60

Would you take on your significant other's religion if they had one?

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#61

Deep Questions To Ask Someone To Know Them Better What’s been your biggest mistake so far in life and what did you learn from it?

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#62

What did your past relationship teach you?

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#63

What’s your favorite book/movie of all time and why did it speak to you so much?

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K- THULU
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Book: "From the dust returned" by Ray Bradbury and film: "Kiki's delivery service", they are both so beautiful , they make me cry every time......

#64

Deep Questions To Ask Someone To Know Them Better What’s the best piece of advice someone has given you?

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#65

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

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That there's nothing under a car's engine. As in that space is not covered from the bottom.

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#66

Is flirting cheating?

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#67

Deep Questions To Ask Someone To Know Them Better What piece of culture or trend has died out, but you would like to see it make a comeback?

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Headless Roach
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Not that it died completely, but certain music of the 80s still rocks my boat

#68

What kinds of things are normal now but will be highly valued antiques a century later?

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#69

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

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Yeast pate. NOT Marmite, but a homemade spread made out of fresh yeast.

#70

Deep Questions To Ask Someone To Know Them Better What do you really wish you knew when you were younger?

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#71

Who do you make happy?

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Jj321
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My 2 year old. I left him with my mom for a few hours today, the pure joy when I got back was amazing.

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#72

What was the worst phase you went through in life?

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#73

Deep Questions To Ask Someone To Know Them Better What unnecessary products or services do you consider necessary?

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#74

Which fictional villain made you feel real hatred towards them?

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#75

What habit do you have that you think not many other people have?

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#76

Deep Questions To Ask Someone To Know Them Better If colors had a taste, what would each color taste like?

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#77

What names were ruined for you because you knew someone terrible with that name?

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#78

What would an amusement park filled with your biggest fears be like? What rides would it have?

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#79

Deep Questions To Ask Someone To Know Them Better What do people really need to chill out about?

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#80

If you could switch genders for a length of time of your choosing, would you? And if so, how long?

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#81

What silly thing do you take a lot of pride in?

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#82

Deep Questions To Ask Someone To Know Them Better How would the world change if health potions existed?

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#83

What would be the absolute perfect day?

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#84

What is the strongest animal you could win against with just your bare hands and feet?

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#85

Deep Questions To Ask Someone To Know Them Better What event from the past do you most want to see a recording of?

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#86

What is something you probably should do, but will never do?

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Bored Retsuko
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I have a couple of medical surgeries pending that I've been postponing for years...

#87

What great idea would you like to try if you had enough money?

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#88

Deep Questions To Ask Someone To Know Them Better Do you like or dislike surprises? Why or why not?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Absolutely not. I make appointments for months out just so I have mental prep time.

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#89

What is your favorite book to read?

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#90

What are your hobbies?

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#91

Deep Questions To Ask Someone To Know Them Better If you could choose to do anything for a day, what would it be?

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#92

What is your favorite family vacation?

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#93

Who would you want to be stranded with on a deserted island?

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Helena
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Botanist. They'd be most likely to know what was edible.

#94

Deep Questions To Ask Someone To Know Them Better What did you want to be when you were small?

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Rose the Cook
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

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.,

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#95

If money was no object, what would you do all day?

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#96

What is the worst gift you have received?

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#97

Deep Questions To Ask Someone To Know Them Better What’s on your bucket list this year?

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#99

What qualities do you admire about your parents?

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#101

Would you ever take back someone who cheated?

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#102

What is a relationship deal breaker for you?

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#103

Deep Questions To Ask Someone To Know Them Better When do you think a person is ready for marriage?

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#104

What’s your biggest regret in life?

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#105

Do you believe in second chances?

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#106

Deep Questions To Ask Someone To Know Them Better Where is your favorite place in the entire world to go?

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#107

Why did your last relationship end?

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#108

Are you confrontational?

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#109

Deep Questions To Ask Someone To Know Them Better What’s your “and then it got worse” story?

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#110

What was something you ate regularly as a child but now cringe at the thought of eating?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Nothing. But I eat lots of things I used to cringe at when I was little.

#111

What’s the craziest thing you’ve ever done for love?

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#112

Deep Questions To Ask Someone To Know Them Better If you were given $15,000 to give the most amount of happiness to the most amount of people, what would you do?

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#113

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

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#114

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

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#115

Deep Questions To Ask Someone To Know Them Better What do you think people automatically assume about you when they look at you?

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#116

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

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#117

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

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#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?

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#121

Deep Questions To Ask Someone To Know Them Better If you could dedicate your life to solving one problem, what problem would you choose?

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#123

What was the best thing about how your parents raised you?

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#124

Deep Questions To Ask Someone To Know Them Better If jobs/careers had slogans what would be some of their slogans?

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#125

Why do you think we dream?

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#126

What’s the most stress relieving thing you can get/do for less than 20$?

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Lousha
Community Member
1 year ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Plant a seed, watch it grow. Also knitting, but you can't do much of it for that much money.

#127

Deep Questions To Ask Someone To Know Them Better How do you feel about God?

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#128

What scrambles your brain every time you think about it?

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#129

If you could change your first name, what would be the most epic name you could choose?

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#130

Deep Questions To Ask Someone To Know Them Better If you were given immortality, but there was one condition, what would stop you from accepting immortality?

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#131

What would you change about yourself if you could?

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#132

What is your favorite thing about your career?

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#133

Deep Questions To Ask Someone To Know Them Better What is the best gift you have been given?

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#134

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

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#135

Who is your favorite author?

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#136

Deep Questions To Ask Someone To Know Them Better What is your ideal meal?

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#137

What’s the biggest lie that a guy has told you?

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#138

How often do you go into a room and forget why you went into the room?

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#139

Deep Questions To Ask Someone To Know Them Better What did you want to be when you were younger?

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#142

Deep Questions To Ask Someone To Know Them Better What are your highest aspirations?

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