The lives of rich people are clouded in mystery, as many of them value privacy and try to avoid unwanted attention. But this only makes the rest of us more curious to know how differently they live from us and what kind of luxuries complete financial freedom can buy. So when, once in a while, we get a peek inside, we can’t just keep it to ourselves. 

That’s exactly what was happening under this thread, where people who found themselves in events hosted by the wealthy enthusiastically shared the craziest things they witnessed there. Scroll down to check them out for yourself, and don’t forget to upvote those that surprised you the most!Read More: 50 Shocking Things People Learned About The Lavish Life At Rich People’s Events

#1

When I was in school I got paid $20 to work silent auctions for fundraising events in NYC. Most of them were for private schools in Manhattan. I swiped a credit card for a woman who bid $25,000 for her 5 year old to be principal for a day.

Image credits: krobs42

#2

My friend had a friend who is one of those “crazy rich asian” type of dude. Watch the movie and you will know what i mean.

One day, this rich dude was driving his Ferrari in the toll road, my friend was in another car following him for a car meetup event. This dude crashed his Ferrari to another car, and then stopped in the side of the road. He went out, called someone and waited while smoking with my friend. He acted like normal nothing happened, my friend said.

In 10 minutes, suddenly there was a yellow Lamborghini came up. The Lambo driver went out, took the Ferrari key from the rich dude hands, and then sit inside the crashed Ferrari.

The rich dude drove the Lambo and continue the journey. Apparently the new driver will take the fall for every single crash related problem.

Oh yeah, Police was there the whole time, and they did not bother to talk or approaching the rich dude before the lambo driver came up.

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#3

Not at an event, but at my then 9yr old sons friends house. They were VERY wealthy, and it was the Dads birthday dinner. They were having fillet steak, seafood etc.

Their two sons were disgusted that hey were having fillet steak-AGAIN. And one threw his away, and the other huffed off to his room and demanded his Dad (whose birthday it was) take him to get a pizza.

Dad actually DID! And my macaroni eating kid sat there scoffing his steak and witnessing the majesty of life.

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#4

“So anyway, I had to buy the maid a 1M dollar house so she could live closer to me to do my cleaning everyday. And now she’s not my maid anymore”

Gee I wonder why…

How I wish I was joking 😑.

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#5

“There’s not a huge difference in lifestyle between 10 and 30 million.”

I literally had nothing to relate to. He’s one of my best friends and the kindest guy you’d meet. He drives an older truck from the early 2000s and likes t-shirts and shorts.

Image credits: hobbes8889

#6

My buddy took me on a cruise with our local Ferrari club. The house we went to was owned by a member who had 8 Ferrari’s in his garage, at this house, he also had a real Michael Schumacher F1 car and a Ford GT. While we were there he unveiled his new car a custom built Daytona SP3 that was all completely custom. The base price of the car is around $2.2 million so with the customizations it was closer to $3 million the way he had it.

The crazy part was the story he told about it, this was supposed to be an early build number car but it was delayed. He had to ask Ferrari about why his $3 million dollar car was taking so long while he was putting in another order for a completely custom Ferrari that is probably worth even more than that.

Spending more money on 2 cars than I’ll probably make in my whole life was a pretty wild story to hear while in a garage with cars that collectively are worth more than my family has made all together for a couple of generations really puts the wealth gap into perspective.

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#7

They had a ‘poor people’ themed costume party. I wish I was joking!

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#8

I worked a private event as a waiter, it was a rehearsal dinner. The father of the bride was telling everyone he chartered a private jet for his daughter and son in law to fly to Bali for their 6 week honeymoon, which he has also paid for. The jet was to stay there for their use for the duration of the trip in case they wanted to visit other places if they got bored. The rehearsal dinner for 20 people was about 20k. Working that event was probably the most I ever made in one night at that job, certainly the easiest.

Image credits: pleasantly-dumb

#9

When we were poor our daughter went to a private preschool that was great for her disability and they accepted us at hardly any tuition in exchange for speaking at fundraising events for them on our daughters benefit from being at the school.

At their big fancy yearly ball dinner we were speakers and they sat us at a donor table. We were literally stealing dinner rolls to make our Carl buddig sandwich meat better. At the auction portion one of the ladies explained that last year she bid on and won the African safari but she didn’t have anyone to go with her so she donated it back to this years event. As that vacation came up for bid she goes “wait my niece loves animals and travel, I’ll take her” and she went and bought it for he second year in a row.

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#10

Having to chase someone down because they paid a power bill for a family in need at a charity event, It was $2200 they wrote the check for $22000 said they just heard wrong.

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#11

Through some odd connections I found myself at a private dinner that included the then-current Treasurer of a US state (this was decades ago).

His wife was young and gorgeous and everyone (not me) was drinking steadily. As the night wore on the State Treasurer demonstrated his ability to touch the tip of his nose with his tongue and my connection (the one who got me invited) said, “that’s why he always has a beautiful blond in his arm!”

Raucous laughter all around. Later I said something to my connection about the Treasurer’s wife and they laughed, rolled their eyes and said, *THAT’S* not his wife, that’s his girlfriend – well, one of ’em.

After further discussion it was revealed that every woman there was either a side piece or casual/open thing and most of the men (all VIPs/rich) had wives at home.

Meanwhile I was from a small, coastal (Gulf of Mexico) fishing village and this was the kind of thing I only saw watching *Dallas*. Tame by current “standards”, but back then it was scandalous.

Image credits: EngineerBoy00

#12

Hot tip for anyone that likes art, the best place to see art in places like New York? Auction houses. They change their art every month, most of it will go into private collections and never be seen again, and they are free to visit.

I’ve stood in a room at Sotheby’s in NYC by myself with 5 or 6 Monets….probably $70-80 million worth.

But the two crazy things I’ve seen is you won’t even find rich collectors there. They send their assistants.

And one time I was at Sotheby’s and they were auctioning off a bunch of Tiffany Vases. Some assistant was checking them out, flipping them over, bare hands, just almost tossing them around like soho cups. I was shocked.

Image credits: RudyRusso

#13

I worked at the montage resort in laguna Beach,ca. A centi-millionaire threw a birthday party for himself. He hired John legend and Don Henley to put on a show for him. Henley cost 750k for a couple songs and John Legend was 250k.

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#14

Special service. It was a ritzy wedding and someone there was a congressman. So we had secret service throughout the wedding pretending like they were guests while also not engaging with anyone to be distracted. They were like real life NPCs.

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#15

I once celebrated New Year’s eve at the big house of a rich family.

He was the boyfriend of my girl’s college roommate, met the guy before and he was really friendly.

When outside for a smoke with his best friend he told me the guy was gifted a small castle with 12 permanent staff for his 21st bday.

Image credits: JackFourj4

#16

I attended a rich person dinner in Bel Air. My girlfriend and I hardly knew anyone there but slowly got the sense everyone there was “wealthy.” The house where the dinner was held was listed for $80MM on my Zillow app. At the actual dinner, I began to make small talk with the guy seated next to me. We started talking about traveling, and he said his friend recently “raced with the Porsches in Germany.” I looked at him, and said “oh, you mean he raced Porsches in Germany, that’s great.”

He looked at me confused and said “no, he raced with the Porsche *family*” and rattled off a couple names of the Porsche heirs that apparently they were friendly with.

#17

“There should be a line at the DMV for people like us, then another line for everyone else…”

For context, he’s a super rich lawyer that thinks laws and mores don’t apply to him and others of his status.

#18

Not me but my friend worked catering at this fancy charity auction and said people were casually bidding $50k on a weekend trip like it was pocket change.

The wildest part was when someone bid $20k on a bottle of wine just to immediately gift it to someone else at the table.

Meanwhile my friend was making minimum wage serving them and stressing about rent that month”…”.

#19

I went to school with a lot of crazy rich kids, the richest of whom were normally Russian. A few stick out to me:

It was a boarding school so we had all our stuff there all term. At the end of term one kid piled his stuff on the side of the road, and got into an all-white Rolls Royce as it pulled up. As it left a second all-white Rolls Royce pulled up and collected all his things.

One of the nicest kids you’ll ever meet decided he wasn’t going to go into student accommodation at uni, so he decided to buy a house. I asked him out of interest how much money he had access to. His dad had given him £3.2 million in ‘spending money’ to last him 5 years.

We also had a designated helicopter landing pitch for anyone who flew in.

#20

At a very rich people wedding. The grooms father talking about what a sound financial investment it was for this other rich girl to marry his son. To top it all off the groom was 200% gay.

#21

Went to a wedding in San Francisco 30 years ago. My wife was good friends with the groom. Lots of nice people that I’d never met. Casual conversation with anonymous attendee, he asks me what I do professionally. I tell him that I’m a public employee Union advocate. He tells me I’m the problem with the world and turns his back to me. Similar thing happened to me when a mutual friend introduced me to Reince Preibus. In both instances, “tell me you’re a class warrior on the wrong side of the battle without telling me”. The rich don’t care about being polite or getting along. They drive the steamrollers.

#22

I worked in catering while in law school. Worked a super rich family’s daughter’s wedding where the dessert course was a whole show. A giant ice sculpture of a dove was carted out. Probably 10 ft high. In the middle there was a giant gold ball. Once it got set they pushed two racks of glasses up next to the sculpture on opposing sides. Then, two guys with chrom bore drills drilled into the sides of the sculpture and desert wine came pouring out of the internal globe into the waiting glasses. According to the wedding planner the sculpture was 15k. The wine in the sculpture was close to 50k.

#23

An investor of my company bought a new Bentley SUV because his Cadillac’s battery died.

Image credits: JJGBM

#24

At my former employer we had a client book one of the largest aircraft in the fleet to fly her son to private school in Europe and she accompanied him. She then stopped at a smaller city in Italy for her to visit a restaurant she liked and then returned to the west coast of the US. The bill for this was well over 100k…to drop her kid off at school for the year.

#25

I went to a famous person’s birthday party in Beverly Hills. I won’t say who it was, just in case. But when my girlfriend and I got there, we were escorted up his driveway in a golf cart. Security brought us into his front room where there was a gold piano and then they escorted us to the backyard. First thing I saw was a woman in lingerie in one of those big inflatable spheres floating in the pool. But that was just the side pool. We kept going to the main backyard where there were trapeze artists, more lingerie girls in the bigger pool, a cigar wrapping station, Topher Grace sitting by himself (didn’t seem like he knew anyone there), and a big jazz band playing.

It was the most Los Angeles thing I’ve ever done and honestly didn’t enjoy my time there. We left early because of how self important everyone seemed.

#26

I work at a high end country club. It was raining so we closed the tennis/pickleball/basketball courts. A group of teens came in and asked if they could play basketball. When I told them the court was wet and slippery and they weren’t allowed to play one kid said, there are towels in the locker room, grab some and go dry it off!” It was pouring rain when he said this.

#27

I was once at an all you can eat lobster dinner put on by a company as a reward for high performing employees and a drunk millionaire started yelling at his bosses who were worth hundreds times more than him, because the wine selection was sub par.

I was once told to get my pilot license after complaining about being in a long distance relationship.

#28

I was invited once to a party with very rich people here in México City, nothing too crazy but a guy was casually talking about his new island near Cancún like It was nothing.

Image credits: Spascucci

#29

Not a gala or event, a friend’s wife worked at an HOA in a rich area where some celebs and pro athletes lived. One resident asked her if the airplane paths overhead could be changed to avoid the area. They weren’t even close to the airport, maybe 20 miles.

#30

Private jet sent from Las Vegas back to the Bay Area to pick up leftover brisket from a party hosted by someone in the VC world.

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