There are a few books out there, that ask some pretty interesting questions.
Some of these have really made me think.  

Now let your mind wander…

In your opinion, what is the best piece of music ever written?

If you could have any book instantly memorized cover to cover
which book would you choose?

When you were a child,
what job did you most want to have when you grew up?

If you could walk into any painting and actually experience the moment it depicts,
which painting would you choose?

If you had to choose one flower to wear daily in your hair
or on your lapel, which flower would it be?

Which particular historical document (or portion thereof)
do you think every American should know by heart?

If you had to describe your personality using a Native American name,
what would it be?

What is something you forgot once
that you will never forget again?

A picture is worth a thousand words.
What is one place you have seen that only a picture can adequately describe?

If you had to choose your own epitaph of seven words or less
(besides name and dates), what would it be?

What do you think is the most soothing sound?

Suppose you were asked to redesign the American flag,
What changes would you make?

If you were completely blind but could somehow see for one hour each week,
how would you spend that time?

If you were an artist,
what would be the theme of your paintings or drawings?

If you were given 1,000 fresh roses,
what would you do with them?

If you could be any age again for one week,
what age would you be?

What is one event in the future
whose outcome you would like to know now?

If you had to choose one icon to serve as the national symbol for the word kindness,
what would it be?

For what in your life do you feel most grateful?

When did you last sing to yourself?
To someone else?

Would you accept twenty years of extraordinary happiness and fulfillment
if it meant you would die at the end of the period?

What is your most treasured memory?

If you had to be represented by an object in your home,
what would you choose?

If you were to choose a musical instrument that best describes your character,
what would it be?

If you could accomplish only one thing in the rest of your life,
what would it be?

If you could change the ending of any book ever written,
which one would you pick
and how would you change it?

If you could recover one thing you’ve lost in your lifetime,
what would you wish to find?

If you could sing any one song beautifully and perfectly,
which song would you choose?