I spent 4 days awake playing Guild Wars when I was 20. I finally went and crashed when I got to a point in the game where I decided it was time to go lay down.
The longest is around three days, give or take and people can tell when I get tired when I get angry, A little. Easy, flying from Australia to the UK is a good 24 hours flight and I spent all that amount of hours awake and can't sleep.
I went to Austria with my school. I had never been overseas. I was so excited I couldn't sleep the night before, couldn't sleep on the flight over, and my teacher wouldn't let us sleep until 8 pm so we could cancel out jet lag. I think it was a total of 29 hours.
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