It is a nine-letter word.
The exact opposite of the phrase "friendly and outgoing"
It contains the word "over".
It starts will a vowel.

What is it?

When Jack was six years old he hammered a nail into his favourite tree to mark his height. Ten years later at age sixteen, Jack returned to see how much higher the nail was. If the tree grew by five centimetres each year, how much higher would the nail be?

If you're 8 feet away from a door and with each move you advance half the distance to the door. How many moves will it take to reach the door?

Create a number using only the digits 4,4,3,3,2,2,1 and 1. So i can only be eight digits. You have to make sure the ones are separated by one digit, the twos are separated by two digits the threes are separated with three digits and the fours are separated by four digits

Speaking of rivers, a man calls his dog from the opposite side of the river. The dog crosses the river without getting wet, and without using a bridge or boat. How?

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.

There is something which you can be arrested for attempting but not for successfully completing.

A man dies of old age on his 25 birthday. How is this possible?

Only one colour, but not one size,
Stuck at the bottom, yet easily flies.
Present in sun, but not in rain,
Doing no harm, and feeling no pain.
What is it?

What question can you never answer yes to?