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Hard to say for sure. I slept in my car in heavy snow, which was bad. Was broken down and waiting for pickup, it was quite cold. I slept every night for a month on an attic floor with a bunch of other guys in Belgrade, which was an awesome trip but I got horrible sleep. Interestingly, only days after I left the country was whenever the breakup of Yugoslavia began, so I got out at a good time.

Slept in an old partially broken office chair a few times in a studio, which was very uncomfortable. I personally do not sleep well anywhere outside a bed, although on occasion my comfortable office chair is good enough for me to doze off in, although unintentionally.
 
when i was about 18 i slept in the woods one night , never again.

Haha that’s cute. I slept in a tent during the day in louisiana during some Army training because I was on night shift. Slept in a gun truck in upstate New York winter weather in full gear.

Worst? Probably the nap or two I took during our Spur Ride (its like those civilian Spartan races, but is 24 hours non stop of marching around and doing obstacle courses and such...). It was cold and raining and no cover in the middle of the woods...
 
I slept in my car in heavy snow,

Did the same without snow but something like -5 degrees Fahrenheit (-20 Celsius). Kept a candle going to provide an amazing amount of heat, but quite the smell with the windows closed.
 
Giant roaches, TV that didn't work, air conditioning that couldn't keep the single (rather tiny) room cool, a broken shower that had water running constantly, mirror mounted to the angled wall so that you had to squat down and look up to see in it, walls and floors that looked like they haven't been cleaned since they built the place in the 50s, broken down furniture... I could go on.

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I’ll say as a young adult on a biking trip (as in bicycles) camping in a tube tent, along the C&O Canal in a downpour with water streaming by on the ground. However, I was secure and not yet getting wet, when the older adults in the group decided a nearby hotel would be better. 🙂

Second worse, a run down hotel in Parsons, West Virginia, because it was the only hotel in town. I remember the holes in the wall and mice. Was there for my Aunt’s funeral.

Giant roaches, TV that didn't work, air conditioning that couldn't keep the single (rather tiny) room cool, a broken shower that had water running constantly, mirror mounted to the angled wall so that you had to squat down and look up to see in it, walls and floors that looked like they haven't been cleaned since they built the place in the 50s, broken down furniture... I could go on.

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Where was this? It looks familiar.
 
Holbrook, Arizona on Route 66. It was the inspiration for the "Cone" motel in the movie Cars.
I’ve driven East West and North South in Arizona, but I can’t remember if I saw that in person or in media. And I don’t know how close InterState 10 runs to Route 66 as so I might have seen it in person.
 
The floor of a tiny motel room with like ten other people. If I slept, it wasn’t for more than a half hour. And I was furious with my friend for being too lazy to take us back to our nice hotel room. As soon as there was the barest hint of light, I roused him and we left.
 
Got caught in an unexpected blizzard in the mountains in the 8000-9000 foot level. Pulled into the only hotel around to wait for the snowplows the next day. It specialized in hourly rentals for the local "ladies" who didn't bother changing the sheets. My strict grandmother took it rather well, considering.
 
I'm sure there were quite a few places to sleep I could name. Mostly during travel. But honestly, I don't want to complain about it, because especially in places with difficult living conditions I always met great people. Not all people have the luxury to return home to a four-star bed. So who am I to complain about it.
 
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