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