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Jack is a truck driver from Springfield, Illinois. On one of his trips to Louisville, Kentucky, something bizarre happened. He left Springfield at 8:00 PM and arrived at Louisville 4 hours later. Then he checked into a motel and slept for 8 hours.

When he woke up the following day, it was already 10:00 AM.

How did this happen?

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Reasoning

Firstly, Kentucky is in a different time zone (Eastern Standard Time) to Illinois (Central Standard Time) which means the time difference is already one hour.
Secondly, the clocks go forward for daylight savings in March so if Jack stayed over when this happened (say from Saturday to Sunday, 9th-10th March, 2019) this would cause another hour in difference in the time.
Overall this would push the time forward by two hours which is the discrepancy.

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Another reasoning

without invoking DST

just because

1 hour is the time zone difference (so Jack arrived at Louisville at 1:00, Kentucky time), and 1 more hour is the time used for parking the truck, checking in, etc. (since it cannot be done momentarily and requires some time, so he arrived at the city at 1:00, but managed to fall asleep only at 2:00 after doing all that stuff, so after an 8-hour sleep it should indeed be 10:00).

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Maybe

After he checked in he didn't go to bed immediately. So he slept at 2:00 AM

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Jack is a truck driver from Springfield, Illinois. On one of his trips to Louisville, Kentucky, something bizarre happened. He left Springfield at 8:00 PM and arrived at Louisville 4 hours later.

That means he

arrived at midnight

 

Then he checked into a motel and slept for 8 hours.

So,

it was already a new day when he got to the bed. He woke up some time after 8 AM the same (new) day.

and then,

the following day after that,

 

When he woke up the following day, it was already 10:00 AM.

 

he slept a little bit longer.

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