I work in a hotel. A high-tier member of our guest rewards program comes to the desk with his girlfriend.

Guest: “The name is [Guest].”

Me: *Smiling* “Hello, sir, welcome. Ahh, I have your booking right here. Let me print the paperwork.”

Guest: *Glaring and demanding* “I’d like to request an upgrade.”

Me: “All right, let me see. Hmm… you’ve already been upgraded from a standard twin to a king superior with a sofa bed.”

Guest: “I want a suite.”

Laughing nervously, I check the system.

Me: “Sir, we don’t have a suite available. They are occupied.”

Guest: “Yes, you do. You have the presidential suite.”

Me: “Um…”

He pulls out his phone to show me.

Guest: “I see you still have it on your website!”

His quiet girlfriend also pulls out her phone to show it to me twice for some reason.

Now let me stop here to explain some context.

The presidential suite is £800 a night. It’s three rooms with their own balconies. The wallpaper in those rooms is £1,000 a roll. The presidential suite is gorgeous.

I look at this dude’s rate, and he booked a standard twin for £103 for the night. Absolutely not happening.

Me: “Sir, we don’t have the presidential suite available.”

Guest: “As a diamond member, I get free upgrades!”

He shoves the phone showing the available suite at me. At this point, I’m starting to shake because he’s being super forceful, like a guy who would flip out if a woman turned him down at a bar or a child being refused a toy.

Trying to defuse the situation, I look more into the system.

Me: “We have a king-superior sea view tonight that I’d be happy to give you. The diamond member complimentary upgrade only allows for a room type in a category that’s one grade up from the one you book, and we have done that, but I can give you this, the king-superior—”

Guest: “I want to speak to your manager.”

Me: “All right, gladly.”

I go get my manager and explain the situation. He comes out and repeats everything I said. He explains that we can’t give the presidential suite to the guest because the suite is four rooms, but he’d also be happy to give him a king-superior sea view.

Guest: “No, I don’t want that room! That room is rubbish! I stayed in that exact room the last time I was here, and it was dreadful. I want the presidential suite!”

No, he didn’t, and he had no idea what the number of said room would be.

Manager: “Sir, I am not going to give you the presidential suite, but I have this lovely king-superior sea view room available for you.”

The guest whines.

Guest: “I’VE DRIVEN ONE HUNDRED MILES TO COME HERE! I know [Company CEO] personally! The [Hotel Brand] in [Town] lets me have their presidential suite all the time!”

My front office manager stands his ground. The guest sighs.

Guest: “Fine. Cancel my booking, then.”

He’s clearly bluffing.

Manager: *Robotically* “That’s a shame because I have a lovely king-superior sea view for you to enjoy.”

Guest: “No, I want the suite. Cancel my booking. I’m going to another hotel.”

Manager: “All right.”

He does, and that is that. My manager goes to finish paperwork, and I continue my nightly routine, watching the guy and his girlfriend in the lobby fiddle on their phones. After a bit, the guest approaches again.

Guest: “Can I see your manager again?”

My manager sighs and comes out.

Guest: *Sheepishly* “Can you book me a taxi?”

I work in a hotel. We had a guest staying with a woman that he said was his wife (it wasn’t) in a room for a few days. We never saw this lady, and the man said she was ill and kept extending his stay each day to give her more time to recover. At one point, the man came into the lobby.

Guest: “I need to have the sheets changed in my room. My wife soiled herself in the bed by accident.”

The head housekeeper went to the room with fresh sheets. What he found there was disturbing. Yes, the bed was covered in feces, but there were empty plastic vodka bottles strewn about the room, and the place smelled heavily of cigarette smoke, which is not allowed in the hotel. The woman remained in the washroom the entire time the housekeeper was there.

When the housekeeper told us about this situation, I made the decision not to allow them to extend another night if asked. I had already agreed to let him stay that night. The guest came into the lobby later that day.

Guest: “Can I extend my day one more night?”

Me: “I’m sorry, but we’re sold out. You’ll have to check out tomorrow morning at 11:00 am.”

Guest: “I understand.”

The next morning, the man left abruptly at about 9:00 am — without his “wife”. I sent the cleaner up to the room to see what was going on.

At the bottom of the stairs from the rooms, we have a courtyard. In the courtyard, there was a huge pile of the woman’s stuff: backpacks, shoes, garbage bags of clothes, etc. She was nowhere to be found and the room was empty. Assuming the man would be coming back for the clothes and stuff, I sent the housekeepers in to clean the room.

While they were cleaning the room, the woman arrived, walked into the room with a giant bottle of vodka, took off her pants, and laid down on the couch, refusing to leave. It was now past checkout time, so I was called to deal with the situation.

When I arrived, the woman was naked except for an open blouse, revealing a heavily tattooed, sixty-ish-year-old body that had seen some years of heavy drinking.

Me: “Ma’am, I’m afraid I have to ask you to put on some clothes and leave the premises. You do not have a room booked here for tonight, and it is well past checkout.”

Woman: “I’m not going anywhere. I need a nap.”

Me: “Ma’am, if you refuse to leave, I will have to call the police.”

Woman: “You go ahead and call the police.”

She poured herself a drink of straight vodka and shot it back.

I went back to the office and called the police.

Me: “Officer, we have a woman that refuses to leave a room she is not booked into. She isn’t staying here tonight, but she won’t leave.”

Officer: “Is she naked?”

Me: “Ummm… yes. How did you know that?”

Officer: “Oh, she’s a regular. We’ll come get her.”

And that was that. They came and took her away, but the belongings were never retrieved by anyone.

I have a rather large friend group from college that started as a weekly board game group with eight members and grew over time to a group with (currently) eighteen members. Over the last several years, however, many of our friends have graduated and moved out across the US. These close friends have since been missing out on getting to hang out, and a lot of the original group members have never met some of the newest members.

As a result of missing our friends, we start planning a get-together for early next year. As my husband and I were the first in the group to get married, we are the sort of de facto “parents” of the group, so we get put in charge of planning and setting up the hangout.

I start looking on a popular app for rentals for a weekend get-together that will fit with our lowest-budget members. I find a couple I like and send everyone some options.

We pick a place and a date, and I reach out to the host to explain what we’re doing and make sure they’re on board with our plans. Everything is a go, and all my friends, being decent people, send me their share of the cost of the rental.

I go to my computer and set up the rental with the right number of guests (seventeen), the dates (two months away), and the location (five minutes from where I live and the college we all attended). I put in my payment information and hit submit.

The rental returns an error message, informing me that my reservation has been flagged as a “party risk”, so I can’t book this stay. For context, [Rental App] doesn’t allow parties to be hosted at any of their locations due to the high risk of damage to the host’s homes.

Okay, no problem. I reach out to the host again, tell her that the site wouldn’t let me book, and ask her for a pre-approved booking invitation to allow me to book. The host agrees and sends me the invite.

I follow the link, set it up again, and hit “reserve”. The same error message pops up; I’m not allowed to reserve the stay.

Okay, fine, the system’s a little buggy. No big deal. I reach out to the support team and tell them what’s going on. The host knows about the friend reunion and knows we accept responsibility for any damages that occur during our stay, etc.

I get connected to a support member via live chat.

Support Member: “The error you’re seeing is an automatic flag because you hit certain conditions for ‘possible party’. Namely, you’re booking a short stay in a large house for a lot of guests, you are under twenty-five, and you live locally.”

Me: “Okay, I understand. The host is on board, though, and is willing to let us stay. We just want to come to play board games and eat junk food with our long-distance friends for a weekend.”

Support Member: “This flag is not reversible. There is no possible way for you to book this stay. Neither the [Rental] host nor I can override this restriction.”

Me: “I want you to know that I don’t blame you for this, but this is really stupid.”

I ended up having to reach out to one of my friends, who is twenty-four and lives in a different state, to book the stay with her account instead. She booked exactly the same location for exactly the same dates and price with the exact same people attending. But she lives in a different state, so it’s fine. Dumbest system I’ve ever heard of.

I’ve been working in the hotel industry for about four years now, and due to a good program and performance, I am already a duty manager. I’ve been interacting with a lot of fussy guests over the years who know that crying for the simplest things will get you freebies. But this one lady really got on our nerves.

It’s one of those days when we are almost sold out, and the upcoming days are either sold out or very tight, especially on the higher-category rooms. I’m there in the lobby in the late evening with just one arrival left for the day. It’s booked under the name of [Guest] and made for a basic-category room with an occupancy of two adults.

A car pulls up to the main porch, so I think, “Yay, the final arrival is here! I can just finish this off and chill for the rest of the shift.”

Oh, how wrong I am about to be.

Out of the car come two adults, three kids, a nanny, and a toddler, and — I am not exaggerating — eleven pieces of luggage.

I think this has to be some sort of canceled reservation and I am about to deal with telling a person who didn’t check his mail that we can’t honor his reservation. Nope, it’s [Guest].

Guest: “Hi. We would like to check-in. We are very tired.”

Me: “Of course, ma’am. Could you help me with your name and your reservations?”

Guest: “It’s just one reservation — under [Guest].”

Me: *Visibly confused* “But ma’am, this reservation is booked for only two people, and I can see that you are traveling with more than that.”

Guest: “Well, I spoke to your colleague, Mr. [Person], and he confirmed that I can just take your Prime Luxury Suite in the hotel on arrival. I see on the website that it can accommodate six people, so I want that. I spoke to Mr. [Person] working for you, and I want your Prime Suite as he said we can all fit in that. Go ahead and upgrade me.”

Me: “We have only one Prime Luxury Suite in the hotel, and it’s already sold out for the entire length of your stay, as this is the busy season. Also, we do not have anyone named Mr. [Person] that works for us.”

[Guest] explodes and starts screaming.

Guest: “You are so uncoordinated! Mr. [Person] does work for you, and he promised me that suite! I demand to speak to your duty manager!”

You are looking at him, crazy lady.

I finally told her basically that there was no way the room she’d booked could accommodate her entire clan and that she needed to book an extra room. Even doing this would mean that we’d have to oversell the hotel by a room for one of the days because of her, but I’d speak to higher management and get that done. After a lot of arguing and showing her the room, she finally reluctantly agreed, scoffing the entire time about how she was going to leave a bad review and so on.

Still, doing my job, I processed the new reservation and even gave her an interconnected set of rooms — two rooms with a door in between.

Over the course of her stay, she complained multiple times about laundry, food, and services to try and get as many freebies as possible, and as soon as she checked out, we decided to add her straight to the Do Not Rent list. We never got that bad review that she talked about, only bad vibes from her throughout the stay.

I work in a hotel in Rome, Italy.

Guest: “Do you know any official sellers of the ruins’ flints? I’d like to take a piece of the fora with me, but taking it myself isn’t allowed, and I can’t find anyone on Google that sells those.”

As I talked, I finally understood that the guest was absolutely convinced that people were fined for chipping the Colosseum away because “ruin flinting” was a protected traditional activity of sorts, allowed only for Romans. The idea of it being damaging never crossed her mind, it seemed.