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It's late in the evening.
I advance along a street with a shoe in my hand. 
I cannot proceed, I have to stop.
Next to me stands a hotel.

"Darn, I am seriously screwed" I exclaim.

What has happened to me?

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3  
Welcome to PSE! As a note, be aware that this type of question are often closed due to being too broad. It is difficult to write one that will pass the scrutiny of this site. You may get a fair number of answers that fit the prompt (if somewhat loosely), but are not your intended answer. But keep bringing good puzzles! – Aggie Kidd Feb 5 at 15:30
    
@AggieKidd thanks for the heads-up and for the edit! :) – Federico Feb 5 at 15:31
    
Doing well! I hope this stays up. I like it. – Aggie Kidd Feb 5 at 17:38
    
I remember a very similar puzzle about "pushing a car or something" and I think it's got deleted by the mods. – AeJey Feb 8 at 9:45
up vote 39 down vote accepted

You are

Playing Monopoly with the shoe trinket. A hotel means you have to pay the property owner a large sum of money.

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Works for every clue except the time of day - not sure if that's a red herring or somehow relevant... – Darrel Hoffman Feb 5 at 17:56
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@DarrelHoffman This was the obvious answer, to me. I assume the "evening" bit was just flavor (also, how often does this scenario happen not-in-the-evening?) – question_asker Feb 5 at 18:02
6  
Late in the evening could imply a game that has been going for a while. It takes time to work up to having hotels. – Regan Feb 5 at 19:09
2  
I would argue that the combination of evening (meaning the game has gone on a while) and the last line (being screwed) likely mean that this has bankrupted the player, ending the game for him/her. – Joel Rondeau Feb 5 at 19:44
    
This was my first idea too (due to the word "advance") – JGreenwell Feb 6 at 1:47

Also unlikely, but worth a shot:

You have illegally parked in front of the hotel, and the police have placed a Denver Boot on the wheel. You have your hand on the Boot trying to get it off, but you know it will not work. Since it is night time, it may be difficult to get someone to come out to remove it until morning, so you are stuck where you are.

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This is not what I had in mind, but I upvoted it nevertheless since it uses all the elements. – Federico Feb 9 at 7:57

Super unlikely to be it, however:

You are a female who was wearing 5" high stiletto heels but one of them broke, so you took it off so you could walk properly. As you see the hotel you realize that you can't keep walking home because your feet are too sore but you can't afford to stay in the hotel for the night ;)

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6  
I reckon one can hardly walk properly with one heel on and one heel off, regardless of gender. – Will Feb 5 at 16:20
1  
Maybe the intact shoe is off and the one with the broken heel is left on to protect the foot from the ground? ;) – SnyperBunny Feb 5 at 16:25
    
This is not what I had in mind, but I upvoted it nevertheless since it uses all the elements. Regarding the heel, I can assure that even a 5mm heel (less than 1/4" for you americans) is uncomfortable to walk without, regardless of gender. – Federico Feb 9 at 7:57

Well it has everything:

its just after midnight of the day your casino commission dealer license expired. The shoe is a blackjack deck. You left earlier but found yourself trapped by a weird artifact of a hotel-casino's ground footprint with no way out without crossing back through the casino floor. Since your license expired you would be in serious trouble if found with gaming materials on the casino floor of the hotel.

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