Tricky Riddles for Adults Who Love a Challenge

I begin sorrow and end sickness. What am I?

I am in you, on you, and deadly around you. What am I?

I run, have a mouth, and sleep in a bed without sleeping. What am I?

I come from a mine and live in a wooden case. What am I?

My life is measured in hours and I serve by expiring. What am I?

What disappears when you say its name?

Forward I am heavy, backward I am not. What am I?

I have cities, mountains, and water but no people, trees, or fish. What am I?

I speak and hear without a body. What am I?

I have keys, space, and enter but no locks or rooms. What am I?

What flies without wings and cries without eyes?

I appear in water but never get wet. What am I?

The maker does not need me, the buyer does not use me, and the user cannot see me. What am I?

Scratch my head and I turn black after being red. What am I?

I have branches but no fruit, trunk, or leaves. What am I?

What can be broken without being held?

What grows shorter as it works?

What has one eye but cannot see?

What gets sharper the more you use it?

What has a ring but no finger?

What word becomes shorter when you add two letters?

What has a head and tail but no body?

What belongs to you but others use more?

What has many teeth but cannot bite?

What can fill a room without taking space?

What is bought by the yard and worn by the foot?

What begins with an E and contains one letter?

What has four wheels and flies?

What answer can never be yes?

What turns clever adults into second-guessers?