15+ Encounters With Rich People That Turned Into Pure Comedy

Crossing paths with extremely wealthy people can be like entering a parallel dimension. Their jokes, requests, and comments may seem a bit off at times, but that’s why they’re so funny. In this article, we have collected real and hilarious anecdotes that users have shared about their most bizarre encounters with people who clearly live in another plane of reality (and bank account).

• The one that gets to me was at our Seafood Sunday Special. There were two rich women in a booth and one of them ordered half a pound of shrimp and crab legs. We were all friendly and I placed the order. I brought her food out when it was ready and asked my usual question, “Does everything look good?” They said it looked great and I told them to enjoy it. But as I was leaving, the lady with the seafood said, “You’re not even going to bring me a glass of milk?” I was confused because that’s disgusting and I thought she was joking, but she insisted that milk goes well with her shrimp and crab legs. I still thought she was joking, but I brought it to her and she actually drank it with her food. At the end, I asked if everything was okay when they finished, and this lady told me I did great, but I should remember to bring milk the next time someone orders seafood. I know it’s not the weirdest thing on here, but it really gets to me because it seems so disgusting and she acted like I was the stupid one for not knowing. © tboso / Reddit
• I work at a private high school, and every year each class begins with an overnight class retreat. One year we couldn’t find a place to take the junior class, so one of the parents just BUYED A SUMMER CAMP, and the junior class had their retreat there. © PolyThrowaway524 / Reddit
• Some honeymooners insisted that they would not sleep on a mattress that someone else had slept on, so we had to buy a new mattress for each hotel they stayed at. Each mattress cost over $5000 and they stayed in 5 hotels. They only used each mattress for a few nights and then we had to remove the mattress from the hotel and dispose of it. © 0---------------0 / Reddit

• My first teaching job was at a private middle school in one of the wealthiest enclaves in the United States. I taught a kid who told me he hadn’t finished his homework because his helicopter had stalled over the weekend and he couldn’t leave his family’s island. He was telling the truth. © ReddishWedding2018 / Reddit
• I know someone who worked for a very wealthy person, probably worth billions. He had over 100 employees, including cooks for the staff... all while being divorced and living alone. But the funny thing was that he had one “trivia” employee. He had hired him specifically to tell him interesting facts and stories on a daily basis. That was his only job. Someone else was hired to take care of his shoes. Polish, shine, everything. If I hadn’t heard it firsthand, I wouldn’t have believed it. © mambo-nr4 / Reddit
• One of my clients bought a newly built penthouse and wanted a hot tub on the balcony. But he needed a structural column in the middle of the balcony below, which the contractor who built the condo did not want to do because it would affect the sale of the entire condo. So what did my client do? He literally BUYED the unit below, approved the column, installed the hot tub, and sold the unit below. Voila, problem solved. © kl_dudey / Reddit

• In college, while we were talking about winter break plans, my friend said that her family was going skiing in Switzerland and that they were planning to leave after her last final exam. I thought, “What if she get delayed or something?” so I asked her what time the plane left. She looked at me very confused and said, “When I get there.” It turned out that her family had their own plane. They would fly from their house to the airport closest to the university, refuel, and when she was done and arrived at the airport, they would leave for Zurich. She felt confused because the plane always takes off when she arrives. She has never flown commercial in her life. © ManyAreMyNames / Reddit
• I had a client (I’m a wedding caterer) who had rented one of the most expensive venues in town. EVERYTHING at the event was designer, and overall she had spent more money on the wedding than was necessary, to say the least. None of this mattered on the morning of the wedding, however, when her mother showed up wearing the wrong shade of green. The bride spent an hour yelling and crying at her mother, messing up her makeup, and setting back her entire day’s schedule. She was fined more than the original cost of the venue rental, and all the vendors were charged overtime for being forced to stay past midnight. And all this drama only to find out later that the bride never actually had a job and her parents paid for everything and the marriage didn’t even last 6 months. © ReignTX21 / Reddit
• When I was 20, I dated a girl whose father was rich. One year she took me to spend Thanksgiving at her family’s “retreat” in the mountains. While my girlfriend was giving me a tour of the place, she showed me her father’s study/library, which had a display case with about 20-30 trophies. Her father’s name was engraved on them, but all other details were blackened or covered up. I wanted to ask what the trophies were from, but was told that under no circumstances could I ask that, because we were not even allowed to go in there. © Taskerst / Reddit

• A girl at my school was “surprised” by her parents in the school parking lot with a brand new BMW. A freaking BMW. Everyone outside was basically watching with their mouths open when she started crying. At first we all thought it was because she was so happy, but then she ran into the school. Apparently they were supposed to show up earlier (I guess when there would be more students to witness the surprise). I felt bad for the father because he seemed so embarrassed and sad. © PazzaCiccio / Reddit
• Once, when I told my boss that we had finished the job ahead of time, he took off his expensive watch and gave it to me, saying, “Good job.” © SuvenPan / Reddit
• In college, this rich guy kept trying to impress me. I wasn’t interested. Then one day, the hallway to my class was filled with dozens of flowers. At the end was a card: “Just say yes.” I laughed, until the professor called me in and said someone had anonymously donated $75k to cover my tuition. The donor note just said, “No pressure. Just dinner?”

• My sister married into money. I went to visit her for dinner once and I drove a beater ragtop, my brother-in-law had always had “sensible” cars. He was crazy about the convertible and asked me to take him for a drive, he loved it and when we came back he told my sister they needed a convertible. My sister says no and tells him they’re not convertible people. BIL is defeated and says ok and he’ll go get dinner while my sister and I catch up. The guy is out for 3 hours, comes back with a pizza and drives a brand new 2001 Saab 9-3 convertible. I was blown away that he could do that so easily, he was gone 3 hours because he wanted to pay for it in cash and they had to verify that his money was real and he wasn’t a mobster or something. © CanadianExiled / Reddit
• I used to work in a high-end boutique in the San Francisco Bay Area where many affluent women came to shop. One day a woman came in looking for a “basic t-shirt” after spilling something on the shirt she was wearing, which she was “just going to throw in the garbage after wearing it anyway” because she didn’t need it that bad, just for the rest of the day. The “basic” shirt was just a plain white V-neck tee, but it cost $80 because of the brand. I was making $9 an hour and couldn’t afford anything the store was selling. © beard_lover / Reddit
• I didn’t see it, but my dad did. He’s a carpenter, and one of his clients hired him to build a fully functional pizza oven in the kitchen of their house. He did. Afterwards, while my dad was getting paid, he asked if his family did a lot of homemade pizza, to which the client replied, “No, my wife just ’needed’ (key word) a place to keep the pizza warm when we order it from Dominos.” © HowDoIGetToFacebook / Reddit
• On my first day at a fancy restaurant, I served a couple who looked rich. The guy ordered the most expensive dish in the menu, but didn’t touch it. After some time, he said, “You can take it, but charge me for the food.” Confused, I asked him why, and he revealed... “Because I didn’t want to eat, I just paid for the experience of watching it being prepared.” I looked at him with a “What?” face, but continued with the order. In the end, he paid the bill as if nothing had happened and left a tip even bigger than the food. I didn’t know if he was joking or doing something much stranger than just spending money.

These stories confirm one thing: when money is no limit, logic is no limit. We laughed, we were surprised, and in some cases we couldn’t believe what we were reading. Looking forward to more unusual moments? You can read this article here, with new gems from the millionaire universe that will leave you just as perplexed.