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Deep Questions To Ask Someone To Know Them Better

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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.

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#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?

14points

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.

7points

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#2

If you could share a meal with any 4 individuals, living or dead, who would they be?

13points

Eat Dirt Crow 2 years ago

Oh, living, for sure.

13points

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#3

What was the worst phase in your life?

13points

Albino 2 years ago

That's not something I talk to ransoms about.

0points

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#4

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

11points

Helena 2 years ago

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.

3points

#5

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

11points

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.

3points

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#6

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

10points

Headless Roach 2 years ago

Give ‘em to the one who needs them more

2points

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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?

9points

Lousha 2 years ago

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

5points

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#8

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

9points

Helena 2 years ago

Be reassured that I must've picked correctly.

2points

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#9

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

9points

Shyla Bouche 2 years ago

How would I order Uber?

3points

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#10

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

8points

#11

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

8points

Lousha 2 years ago

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.

2points

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#12

What do you most look forward to about getting old?

8points

Jane Martin 2 years ago

already there! Retirement is wonderful

3points

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#13

Deep Questions To Ask Someone To Know Them Better What are you most grateful for?

8points

Shyla Bouche 2 years ago

My best friend.

0points

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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?

8points

Shine Chisholm 2 years ago

Capitalism

2points

#15

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

8points

Melissa 2 years ago

The number of cats and dogs I've pet and how often.

3points

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#16

Deep Questions To Ask Someone To Know Them Better What options would come up if you could “right-click” people?

8points

Shine Chisholm 2 years ago

Get more info

1point

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#17

What motivates you to work hard?

7points

Lousha 2 years ago

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.

2points

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#18

What really makes you angry?

7points

K- THULU 2 years ago

Rape, sexism, misogyny....

1point

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#19

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

7points

Headless Roach 2 years ago

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

0points

#20

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

7points

Helena 2 years ago

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

0points

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#21

What makes you laugh the most?

7points

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.

1point

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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?

7points

Helena 2 years ago

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

0points

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#23

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

7points

Lousha 2 years ago

Everyone I touch would suddenly have empathy.

2points

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#24

What are you most thankful for?

7points

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#25

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

7points

Headless Roach 2 years ago

Is that a tricky zombie question?

3points

#26

Have you ever lost someone close to you?

7points

Helena 2 years ago

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

3points

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#27

What’s your philosophy in life?

7points

Headless Roach 2 years ago

Sarcasm. Use it or lose it.

0points

#28

Deep Questions To Ask Someone To Know Them Better What do you wish you could re-live in your lifetime?

7points

Jane Martin 2 years ago

nothing or all of it

1point

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#29

What do you wish you had more time for?

7points

Shine Chisholm 2 years ago

I have the time. I need the energy

3points

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#30

How often is your brain on autopilot?

7points

#31

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

7points

Erin Ward 2 years ago

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

0points

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#32

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

7points

Helena 2 years ago

Corporate farming. Heartbreaking

1point

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#33

What do most people overestimate or underestimate about you?

7points

Bored Retsuko 2 years ago

Underestimate my age.

0points

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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.)

7points

Jane Martin 2 years ago

none

3points

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#35

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

6points

#36

What is your family member’s proudest accomplishment?

6points

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#37

Deep Questions To Ask Someone To Know Them Better What is your biggest fear?

6points

Lousha 2 years ago

Outliving my parter.

1point

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#38

Have you ever had a nickname? What is it?

6points

G҉A҉C҉H҉A҉ A҉L҉E҉X҉ 2 years ago

Mine was moo. Yes I loved cows, so I became one. 🐄

1point

#39

What is your proudest accomplishment?

6points

Helena 2 years ago

Being there for my sister.

0points

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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)?

6points

Erin Ward 2 years ago

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

2points

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#41

Where do you see yourself in five years?

6points

Headless Roach 2 years ago

Have I stumbled on a job interview by accident?

4points

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#42

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

6points

Helena 2 years ago

I want to see Angkor wat in its heyday.

1point

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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?

6points

K- THULU 2 years ago

Music and music....

1point

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#44

How would your friends describe you?

6points

Headless Roach 2 years ago

Crunchy under shoe, no brain, nothing to write home about

2points

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#45

Do you consider yourself an introvert or an extrovert?

6points

Helena 2 years ago

People are exhausting

1point

#46

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

6points

#47

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

6points

#48

What was the best phase in your life?

6points

Lousha 2 years ago

Now.

0points

#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?

6points

Helena 2 years ago

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

0points

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#50

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

6points

Lousha 2 years ago

Better health would be nice.

2points

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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?

6points

Helena 2 years ago

Throw snacks at me. Back out of the room slowly.

1point

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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?

6points

Lousha 2 years ago

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

1point

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#53

What is your idea of a perfect vacation?

6points

Lousha 2 years ago

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

2points

#54

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

6points

Lousha 2 years ago

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

0points

#55

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

6points

Jj321 2 years ago

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

0points

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#56

What kind of parent do you think you will be?

6points

Headless Roach 2 years ago

This ship has sailed

2points

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#57

Do you judge a book by its cover?

6points

Shine Chisholm 2 years ago

It's the whole point of the cover

2points

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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?

6points

#59

Are you religious or spiritual?

6points

Jane Martin 2 years ago

spiritual

1point

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#60

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

6points

Lousha 2 years ago

I would not have a significant other who has a religion.

1point

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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?

6points

Helena 2 years ago

Nothing I'd admit in public.

1point

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#62

What did your past relationship teach you?

6points

#63

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

6points

K- THULU 2 years ago

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......

2points

#64

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

6points

#65

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

6points

Lousha 2 years ago

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

0points

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#66

Is flirting cheating?

6points

#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?

6points

Headless Roach 2 years ago

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

1point

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#68

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

6points

#69

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

6points

Lousha 2 years ago

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

1point

#70

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

6points

#71

Who do you make happy?

6points

Jj321 2 years ago

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

0points

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#72

What was the worst phase you went through in life?

6points

#73

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

6points

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#74

Which fictional villain made you feel real hatred towards them?

6points

#75

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

6points

#76

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

6points

Melissa 2 years ago

I highly suspect orange would taste like an orange.

2points

#77

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

6points

Headless Roach 2 years ago

Sit down, we’re gonna need a moment there

3points

#78

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

6points

Erin Ward 2 years ago

Crowds of people

2points

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#79

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

6points

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“Ma’am I Live Here”: Woman Refuses To Back Out Of Driveway, Learns A Lesson The Hard Way

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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?

6points

K- THULU 2 years ago

Yes... Forever...

2points

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#81

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

6points

Helena 2 years ago

Story telling, or make people laugh.

1point

#82

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

6points

#83

What would be the absolute perfect day?

6points

#84

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

6points

Elizabeth Lloyd 2 years ago

I'm going with hamster 🤔

0points

#85

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

6points

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#86

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

6points

Bored Retsuko 2 years ago

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

0points

#87

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

6points

#88

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

6points

Helena 2 years ago

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

1point

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#89

What is your favorite book to read?

5points

#90

What are your hobbies?

5points

#91

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

5points

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#92

What is your favorite family vacation?

5points

#93

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

5points

Helena 2 years ago

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

0points

#94

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

5points

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.,

0points

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#95

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

5points

#96

What is the worst gift you have received?

5points

Helena 2 years ago

Barbie

0points

#97

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

5points

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“This Breaks My Heart”: People Stunned—And Angry—After Woman Buys Lost Luggage From Airport

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#98

How would you describe your best friend?

5points

K- THULU 2 years ago

Non existent?

2points

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#99

What qualities do you admire about your parents?

5points

#100

Deep Questions To Ask Someone To Know Them Better Does your job make you happy?

5points

K- THULU 2 years ago

Fk no....

0points

#101

Would you ever take back someone who cheated?

5points

#102

What is a relationship deal breaker for you?

5points

#103

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

5points

#104

What’s your biggest regret in life?

5points

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"I Didn't Start The Dryer": Karen Gets Taught A Lesson After Throwing Out Neighbor's Wet Clothes

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Guy Divorced 3 Years Ago Drops Off 3 Y.O. With His Ex-Wife Completely Out Of The Blue

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#105

Do you believe in second chances?

5points

#106

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

5points

#107

Why did your last relationship end?

5points

#108

Are you confrontational?

5points

#109

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

5points

#110

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

5points

Lousha 2 years ago

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

1point

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#111

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

5points

#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?

5points

#113

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

5points

Erin Ward 2 years ago

Joining the army

1point

#114

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

5points

#115

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

5points

Lousha 2 years ago

That I'm much younger. No, it's not flattering, it's annoying.

2points

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#116

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

5points

#117

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

5points

#118

Deep Questions To Ask Someone To Know Them Better What’s your story?

5points

Bored Retsuko 2 years ago

...morning glory

1point

#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?

5points

#120

How decisive or indecisive are you?

5points

K- THULU 2 years ago

Ummmmm....dunno

1point

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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?

5points

Lousha 2 years ago

How to make people less sh***y.

1point

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#122

How often do you feel utterly worn down?

5points

Bored Retsuko 2 years ago

Daily.

0points

#123

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

5points

#124

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

5points

#125

Why do you think we dream?

5points

#126

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

5points

Lousha 2 years ago

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

0points

#127

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

5points

K- THULU 2 years ago

That she will welcome me with open arms when i die......

2points

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#128

What scrambles your brain every time you think about it?

5points

#129

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

5points

Lousha 2 years ago

I love my name.

1point

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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?

5points

Lousha 2 years ago

My partner not being immortal.

1point

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#131

What would you change about yourself if you could?

4points

#132

What is your favorite thing about your career?

4points

#133

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

4points

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#134

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

4points

#135

Who is your favorite author?

4points

K- THULU 2 years ago

Either Michael Moorcock or China Mieville...

0points

#136

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

4points

#137

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

4points

#138

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

4points

Lousha 2 years ago

What room? What was the question?

1point

#139

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

3points

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#140

What’s an ideal weekend for you?

3points

Bored Retsuko 2 years ago

Having NOTHING to do

0points

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#141

Have you ever faked happiness?

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Bored Retsuko 2 years ago

Frequently.

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#142

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

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Damanjeet Sethi

Damanjeet is passionate about cycling and fascinated by sci-fi movies. When not writing, you can find her conducting silly science experiments with her 5-year-old.

Damanjeet is passionate about cycling and fascinated by sci-fi movies. When not writing, you can find her conducting silly science experiments with her 5-year-old.

Eligijus Sinkunas

I’m a visual editor for Bored Panda, trying to find and select high-quality images to enhance articles across different formats. With a keen eye for detail, my goal is to ensure that each picture helps to attract readers into captivating visual experiences. As a freelancer, I’m also working as a video editor for a YouTube channel that makes music games. After work, I like to play with guitar, go to karate classes or just relax at home at play video games.

I’m a visual editor for Bored Panda, trying to find and select high-quality images to enhance articles across different formats. With a keen eye for detail, my goal is to ensure that each picture helps to attract readers into captivating visual experiences. As a freelancer, I’m also working as a video editor for a YouTube channel that makes music games. After work, I like to play with guitar, go to karate classes or just relax at home at play video games.

Marisha Kazaryan

I knew I wanted to be a storyteller ever since I learned to read and write. Fulfilled this dream when I became a content creator and a filmmaker. Also got a degree in English language and literature because grammar is important! Good coffee and good music make everything better. When I’m not telling stories, you’ll find me studying foreign languages (currently, Korean), fangirling over my guinea pig Pepperboy, watching TV shows, and learning to play the drums.

I knew I wanted to be a storyteller ever since I learned to read and write. Fulfilled this dream when I became a content creator and a filmmaker. Also got a degree in English language and literature because grammar is important! Good coffee and good music make everything better. When I’m not telling stories, you’ll find me studying foreign languages (currently, Korean), fangirling over my guinea pig Pepperboy, watching TV shows, and learning to play the drums.

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