John was piloting a plane behind a car but was never able to overtake it. Why?

There were three women in all the swimming costumes!
One was happy and the other two were sad!
The happy one was crying and the sad ones were smiling.
Why was this?

What does this mean?

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I have eight fingers and two thumbs but I do not live. What Am I?

Why do we preferably have round manhole covers and not square ones?

While house hunting in London, I came across a very good leasehold property Discussing the lease the landlady told me:

'The property was originally on a 99 years lease and two-thirds of the time passed is equal to four-fifths of the time to come. Now work it out for yourself and see how many years are to go!

Three cars are driving on a track that forms a perfect circle and is wide enough that multiple cars can pass anytime. The car that is leading in the race right now is driving at 55 MPH and the car that is trailing at the last is going at 45 MPH. The car that is in the middle is somewhere between these two speeds.
Right now, you can assume that there is a distance of x miles between the leading car and the middle car and x miles between the middle car and the last car and also, x is not equal to 0 or 1.
The cars maintain their speed till the leading car catches up with the last car and then every car stops. In this scenario, do you think of any point when the distance between any two pairs will again be x miles i.e. the pairs will be x distance apart at the same time ?

John replied, when asked how old he was. In 2 years he will be twice as old as he was five years ago.' How old is he ?

In a rainy season, one day 3 huge ladies walked under a normal-sized umbrella.
The umbrella is not huge enough to accommodate all 3 ladies yet not a single lady got wet. Why?

What is the longest word in the dictionary?