Deep Questions

Random Deep Questions List

101 deep questions to ask people, your friends or someone you know....

What is more difficult for you; looking into someone’s eyes when you are telling someone how you feel, or looking into someone’s eyes when they are telling you how they feel?

Think of the last time you were REALLY angry.

You are on a flight from Honolulu to Chicago non-stop. There is a fire in the back of the plane. You get enough time to make ONE phone call. Who would you call?

50+ Really Important And Interesting Deep Questions

800 Questions to Ask A Girl
1000 Questions to Ask your Boyfriend

You are at the doctor’s office and she has just informed you that you have approximately one month to live. a) Do you tell anyone/everyone you are going to die? b) What do you do with your remaining days? c) Would you be afraid?

You can have one of the following two things: trust/love.

You are walking down the street on your way to work. There is a dog drowning in the canal on the side of the street. Your boss has told you if you are late one more time you get fired. What do you do?

50+ Really Important And Interesting Deep Questions

If you could go anywhere in the world, where would you go?

Think of the last person who you really knew that died. You have the chance to give them 1 hour of life back, but you have to give one year of your life. Do you?

Are you the kind of friend that you would want to have as a friend?

Does love = sex?

Deep Questions to Ask People List

Your best friend dies, what would you do?

When and how was the last time you told someone HONESTLY how you felt? when was it? during the day. how was it?

What would be harder for you, to tell someone you love them or that you do not love them back?

What do you think would be the hardest thing for you to give up on?

Excluding romantic love, when was the last time you told someone you loved them?

If you had to go back in time and change one thing, if you HAD to, even if you had “no regrets” what would it be?

Imagine. It is a dark night, you are alone, it is raining outside, you hear someone walking around outside your window. Who do you call?

Would you give a homeless person CPR if they were dying?

Are you old fashioned?

Which would you choose, true love with a guarantee of a heart break or have never loved before?

If you could do anything OR wish for anything that would come true, what would you wish?

Deep Questions to Ask Someone

Why is it only drug dealers and software developers call their clients 'users'?

Does the Little Mermaid wear an algebra?

Do infants enjoy infancy as much as adults enjoy adultery?

How is it possible to have a civil war?

If one synchronized swimmer drowns, do the rest drown too?

If you ate pasta and antipasta, would you still be hungry?

If you try to fail, and succeed, which have you done?

Why are hemorrhoids called "hemorrhoids" instead of "assteroids"?

Why is it called tourist season if we can't shoot at them?

If the black box flight recorder is never damaged during a plane crash, why isn't the whole airplane made out of the stuff?

Really Deep Questions

Why is there an expiration date on sour cream?

If man evolved from monkeys and apes, why do we still have monkeys and apes?

If all those psychics know the winning lottery numbers, why are they still working?

If a mute swears, does his mother wash his hands with soap?

Why do psychics have to ask you for your name?

OK, so what's the speed of dark?

And here is a list of questions I added that were not on the list.

If you add your username to your ignore list, would you not be able to read your own posts?

Why is there braille on a drive up ATM machine?

Why do we park on a driveway and drive on a parkway?

If a pin drops in a noisy classroom does anyone hear it hit the floor?

Deep Personal Questions

Describe your First Intimate Experience

What is the most annoying habit that your girlfriend/boyfriend has?

How well "endowed" is your boyfriend or girlfriend?

Have you ever not made it to the bathroom in time and had an "accident?"

Have you ever been extremely "intimate" with someone in a public place?

What is the most embarrassing thing you've ever done?

Have you ever cheated on your boyfriend/girlfriend?

If you had only 24 hours to live, what would you do?

What is the strangest dream you've ever had?

If you could make anyone in the room your servant for the day, who would it be and what would you make them do?

If you could be born again would choose to be a different sex to what you are?

How far would you go with someone that you just met?

What is the stupidest thing you've done because someone dared you to?

What is the stupidest thing you've done on your own free will?

What's your favourite thing about the opposite sex?

What's the worst thing about being your gender?

Have you ever eaten a leaf or grass?

Have you ever peed in the shower?

Have you picked your nose when no one was looking in a public place?

50+ Really Important And Interesting Deep Questions

Deep Thought Provoking Questions

After eating, do amphibians have to wait one hour before getting out of the water?

How can there be self-help groups?

If white wine goes with fish, do white grapes go with sushi?

If a mute swears, does his mother make him wash his hands with soap?

If someone has a mid-life crisis while playing hide and seek, does he automatically lose because he can't find himself?

If someone with multiple personalities threatens to kill himself, is it considered a hostage situation?

Instead of talking to your plants, if you yelled at them would they still grow, but only to be troubled and insecure?

Is there another word for synonym?

Isn't it a bit unnerving that doctors call what they do "practice"?

Just before someone gets nervous, do they experience cocoons in their stomach?

When sign makers go on strike, is anything written on their picket signs?

When you open a new bag of cotton balls, is the top one meant to be thrown away?

When your pet bird sees you reading the newspaper, does he wonder why you're just sitting there, staring at carpeting?

Where do forest rangers go to "get away from it all"?

Why isn't there a mouse-flavored cat food?

Why do they report power outages on TV?

Why are builders afraid to have a 13th floor but book publishers aren't afraid to have a Chapter 11?


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