What question can you never answer yes to?

Make eight squares by moving only two matchsticks.
Note- Square can be of different sizes.

What is the largest amount of money that you can possess in change and still if someone asks you for a dollar, you won't be able to give?

100 prisoners are stuck in the prison in solitary cells. The warden of the prison got bored one day and offered them a challenge. He will put one prisoner per day, selected at random (a prisoner can be selected more than once), into a special room with a light bulb and a switch which controls the bulb. No other prisoners can see or control the light bulb. The prisoner in the special room can either turn on the bulb, turn off the bulb or do nothing. On any day, the prisoners can stop this process and say "Every prisoner has been in the special room at least once". If that happens to be true, all the prisoners will be set free. If it is false, then all the prisoners will be executed. The prisoners are given some time to discuss and figure out a solution. How do they ensure they all go free?

what does this picture(rebus) riddle means ?

I ask Joseph to pick any 5 cards out of a deck with no Jokers.

He can inspect then shuffle the deck before picking any five cards. He picks out 5 cards then hands them to me (Jack can't see any of this). I look at the cards and I pick 1 card out and give it back to Joseph. I then arrange the other four cards in a special way, and give those 4 cards all face down, and in a neat pile, to Jack.

Jack looks at the 4 cards i gave him, and says out loud which card Joseph is holding (suit and number). How?

The solution uses pure logic, not sleight of hand. All Jack needs to know is the order of the cards and what is on their face, nothing more.

What do the following words have in common?

Assess
Banana
Dresser
Grammar
Potato
Revive
Uneven
Voodoo

Below, you can see some coding:
January = 1017
February = 628
March = 1335
April = 145
May = 1353
June = 1064
July = 1074
August = 186

Now deciphering the way it has been coded, can you find out how September will be coded?

What do you get if you add 2 to 100 four times?

On my way to St. Ives I saw a man with 7 wives. Each wife had 7 sacks. Each sack had 7 cats. Each cat had 7 kittens. Kittens, cats, sacks, wives. How many were going to St. Ives?