My older brother is a Tony Award winning producer and I took a trip to NYC ten years ago. His business partner is a former schoolteacher who became friends with a celebrity and got rich producing her stage plays.

Before going to NYC, I called them up and told them "Hey, I'm going to go see the Yankees while I'm there. There are $15 tickets in the outfield. Wanna go?" It was Jeter's last year and I wanted to see him play live at Yankee Stadium. Their response was "Don't worry, we'll handle it."

Handling it meant lunch at the stadium club, with Peyton Manning and a bunch of celebrities in the dining room and lobster piled higher than my head, literally. The most luxurious lunch I've had in my life. Then we rode the escalator down to our seats, through a tunnel lined with every free candy you can think of on both sides, to the second row behind the Yankee dugout, with our own dedicated server, who kept bringing us wonderful drinks. (TEN FEET AWAY FROM DEREK JETER) Then, in the third inning, another surprise: someone taps me on my shoulder holding one of the bases from batting practice, which my brother's business partner purchased and had framed for me with my ticket and a photo.

That was too overwhelming. I couldn't help but cry.

We went for another meal in the 7th inning. The food was still fresh and amazing.

The Yankees lost that day, but it's okay.

I call it my 'Make a Wish' Day.

Growing up poor, and eventually working my way into a tech job dealt me a long stream of culture shocks. Just socialising with people earning over 100k is wild. The vacations, hobbies, and even anecdotes, are all so different than what I imagined. I feel I betray my roots a thousand times a day.

I know this is just basic working class petit bourgeois stuff (that I'm part of), but the carefree attitude is so alien to me. I can't imagine feeling so entitled to luxury.

A friend invited me on vacation with her family. They are very wealthy compared to me. It was clear up front that lodging and meals were covered by them, but I was hazy on everything else. It stressed me out so bad.

Do I want to go with them to do some Expensive Activity? Of course, but am I paying for it? Can I afford it? Even if I can, do I want to spend my limited money on that? Do they see me as a freeloader? How are these other not-rich friends navigating this because no one ever seems to talk about money? Fortunately, my friend saw my stress and had a discrete conversation with me where we set some guidelines.

A girl I dated was friends with the daughter of one of Microsoft's founders and we got invited to their house to watch Seafair. I think it'd be safe to call it a small mansion right on the water with a dock. The kitchen was as big as my whole apartment. The technology was a bit dated but must've been state of the art when it was built. Switches for automated everything. On the water we had front row seats to the Blue Angels. They are incredibly loud up close.

The guy was super down to earth. Had a good conversation where he showed genuine interest in me and what I did.

9.9/10, the hot tub was broken

I stayed a few nights at the St. Regis in NYC in the presidential suite. Pretty ridiculous, 3 bedrooms, 4 baths, private butler, full kitchen and dining room, use of a Bentley, 3,430 sq ft. (318 sqm) bigger than any house I ever lived in.

Through my old job I got to do lots of stupid shit, fly private internationally, use someone's beach house for a week on their own island, etc.

While aspects of it were fun, I always felt like an outsider, and the waste really bothered me. I'm someone who bicycles or walks to the farmers market with a courier bag.

I was an active duty surgical tech in the US military; promoted fairly quickly and ranked up to Staff Sergeant at about 3 years. Shortly after taking that rank, we had a perfect storm of deployments, a retirement, a medical separation, etc that left me as the highest ranking enlisted in the surgery unit, which made me (a still-kinda-newby-surgical-tech) taking the responsibilities of basically a charge nurse. Chief among these was attending morning morning briefs with the top dogs of the hospital (high ranking officers) and giving report. Fortunately I knew where to access the OR's metrics, so my report was always just a summary of our case load, average times, etc.

This lasted only about a week until we got a new Master Sergeant and Tech Sergeant. Apparently I got some pretty high praise from those top dogs for stepping up (not like I had a choice) and doing a decent job -- but that was PURE luck lol. I only did well because things went relatively smoothly on their own. If there was an emergency or something I would have had no fucking clue what to do; and all the junior enlisted seemed to just know that I wouldn't have been able to do shit for them during that time, so everyone kept the smaller fires to themselves during that time.

It was a weird time.

I got very randomly bumped up to first class on a transatlantic flight for business. I do not travel much for business, especially internationally. So, I definitely should not have had priority over more regular accounts. I have to assume I just got lucky, and that flight happened to have no frequent flyers.

It was an eye opening experience. I got to hang out in a secret lounge. When my flight was ready to board, multiple staff escorted us to the gate. When we landed, we took a private van to a secret side entrance, which had its own first class only passport check. We were brought to another secret first class lounge through hidden back hallways to wait for our connections. The lounge looked down over the terminal, and the exit was a nondescript door you'd assume was a maintenance entrance.

Being around that level of service and the other people in first class, it's clear the wealthy live in another world. I looked up how much that ticket normally goes for after, and full price is for many people a yearly salary. It was nice, but it seems like a crazy way to divide resources.

Some of the tax firms my wife has worked for have hosted extravagant Christmas parties in mountain-top restaurants in Banff and the like. We get to pretend we're fancy people and order the most expensive menu items for a night.

I was dating a person who worked in the nonprofit space. They organized a gala focused on education for black students, and I was invited as their +1. It was a super fancy black tie event - something that is far outside of my norm or comfort zone. I met the creator of Abbott Elementary, and she was an amazing person. She even invited me to her birthday party (I didn't go).

Not mine, but my uncle's story. In the late 70s or 80s, can't remember, my uncle was a young man in Boston, MA. New transplant to the US with limited English working minimum wage at a famous hotel in town, by famous I mean all the rock and roll stars stayed in this hotel when they were in Boston. There are other wild stories for another day.

On this day his manager was scrambling to look for him and told him that he had to drive a VIP somewhere. He was speechless, and asked wtf is going on ? He had a humble tiny hatchback manual drive ford fiesta? with only a driver's side mirror. The artist was Blondie and she was late for the show. They wanted the most non descript car to zip halfway through the clogged city to the venue.

He was like wtf, but fuckkit here we go.

He drove the Blondie singer from the hotel to the venue quick and easy like superman and saved the day.

I have to go back and ask what conversation they had.

Flew half-way across the country on a private plane for a business meeting.

The mayor used to know my name. Hollered at me at Mardi Gras!

Went to a party at the woman's house who owns a vast chunk of downtown. Got to see the Mardi Gras parade from above.

I have been picked up by a private airplane once. And I don't mean an private jet like a bombardier global (which are still beyond cool), I mean like a full size long range airliner. The conference room alone was larger than my apartment at the time. Who especially was send my our customer to pick up my colleague and me. Even crazier: As it was somewhat urgent the customer "called" someone in his countries air traffic control and even though we arrived through rush hour at this airport we landed priority - which meant around 12 large airliners had to wait.

(To make that clear: I am not a prostitute, especially as I am a ugly ass overweight dude, but I work in healthcare and did a fair share of VVIP jobs over the last two decades)

Got an extra legroom seat in the airplane by chance.

One of the events that comes to mind was a "open" conference at a university that "actively encouraged" "low class" participation. (They didn't say this).

What I mean by that is that it happened during normal work hours and you had to send an email to sign up, but they did allow you to come.

Over the course of the event it became clear that it was a joint PR thing for the sponsors and the university to appear to be "doing something about [issue]", so they had 2 talks, an audience participation thing, where it was very clear that the thing needed most was more funding for people and work material and tools (think PPE, it wasn't that or that critical). ...and a panel discussion between [company] and [5 politicians] that in absolutely no way addressed the issues that were brought up in the audience participation part.

There was very nice, expensive catering.

Pretty surreal experience and something that solidified my belief that some very important parts of our society are utterly broken beyond repair.

Fundraiser at a very expensive art school. I was a scholarship student at a cocktail mixer, and I was at the mixer because it was being held in the department I was majoring in. All of the people that were attending were fine arts patrons, the kind of people that drop tens of thousands on art without thinking twice about it. I was--literally--a punk kid with tattoos and shit tons of piercings, and I was supposed to be pleasant to people with millions more than I'll ever have.

Got to piss off a world famous fashion designer that evening, so that was cool.

Honestly, where I live now.

I rent a bare-bones townhouse. Two rooms, and a basement with an old washer and dryer, and a small garage.

I have always lived in apartments, sometimes with fewer rooms than people. Having an entire place of my own (that's not a studio apartment) is sometimes unbelievable to me. A washer and dryer downstairs? No quarters? I don't have to look for a spot, I have a garage? I don't have to cram my entire life in one room, I have an "office!?" This will likely be the closest to "home owner" I'll get and it still feels unreal after almost two years here. It's certainly not going into anyone's Pinterest board, and there are issues, but I always feel "bougie" when I open the garage 🤣

Funnily enough, a similar thing. When I was 20 I had a small business, but registered to the business register just like any other. I got invited by email to attend the opening of the new lodge in the stadium (because they were trying to sell me private seats passes I definitely couldn't afford). Shook hands with the players and everything.

I was working the booth at a conference and the sales guys closed some big deal there and took everybody at the conference out to a four star restaurant. Since it was in a legal state me and the woman from marketing got really baked before we went in and had $200 steaks with a $400 bottle of wine. There were like 10 people, too so the whole bill must have been at least $4,000.

She was high as hell the whole time and trying to hide it, which was hilarious for me to watch.

I've also had Iron Chef Morimoto make sushi for me but since I paid it didn't feel above my station.

I've lived in more than one trailer. Including a trailer park. I once slept over at a friend's trailer in a different park. We had a pinecone war with kids from the other side of the trailer park. Pre-bedtime entertainment was Billy Ray Cyrus performing Achy Breaky Heart live on TNN.

I also worked on Capitol Hill, a finance firm worth dozens of billions, etc. My degree is from a shitty Christian college, but I just accepted a job at a prominent research university (staff, not faculty, but still).

I guess I feel like most of my life is relevant to this question.

My parents liked to travel and eat out when we were young. If traveling, it meant we ate with them. I frequently remember eating at very fancy places wearing my little dresses and patent leather shoes and feeling very out of place. But mostly because I was a kid.

Also maybe the one time we flew first class at 14? Oooo they had ice cream!! In real bowls!!! And nice pillows!!!!

I worked at a financial company which had an office in London, I am an IT guy and was asked to go to the London office a few times.

Two of those times I got to stay at The Langham.

It is a far more luxurious hotel than I have ever stayed at before.

One time I went to the restaurant DAMON BAEHREL. I was informed afterwards that it had a 10-year waiting list and only seated 100 people a month. Despite having regularly commuted between the Midwest and the East Coast, getting there felt like the longest road trip I've ever taken since I had to go with my mother-in-law and some of it is on a gravel road.

I had to Google DAMON BAEHREL to spell it and I'm not going to bother retyping it.

It was far and away the most pretentious, absurd, cartoonishly fancy experience I've ever had, and I've dressed up in antique ceremonial Moroccan robes for a banquet at the art museum in the city I grew up in. At the art museum I sat next to the mayor's mother in a room of 200 people conversely, about 30 people total could fit into DAMON BAEHREL.

I thought the art museum banquet was fancy, but when I was little I thought Boston Market and IBC root beer were fancy.

DAMON BAEHREL was the kind of place that serves a dozen 'courses' but each one is like one cracker one sliver of cheese and one spritz of condiment with maybe a sliver of sausage made from some bespoke farm animal. He insisted that the water we were drinking was actually unreduced tree sap. Everything was served on various slabs of wood some with the bark still on it. The slabs were so much larger than the food It looked like putting a coin on a serving platter for each course.

I just felt embarrassed every time I looked at the Damon and his staff. They had clearly heard his bullshit so many times that it was hard for them to feign credulity anymore.

Anyway, that shit was way too fancy for me. Clearly it was just wasted on me.

Years ago my dad took me with him to a business trip in downtown LA. He finished his meeting and we wanted some dinner so started looking around for somewhere to eat. It was in the financial district though, and by 5 or 6 every fast food place around was already closed (which is still weird to me). We were about to give up and go back to our hotel and just get room service until we saw a plain ass sign pointing down an alley that just said "steakhouse." So we followed it into the alley, down some stairs into a sketchy looking basement door that led us into the fanciest fucking restaurant I have ever been in.

Shit was straight out of a movie. The waiters had tuxedos. Everything was finished in nice looking wood, silver or gold. They had an actual maitre d! We immediately felt under dressed and had to ask if there was a dress code.

Saved up for a few years to go to a 5 star hotel resort (thank you COVID!) and when we finally went, goodness gracious was the experience so wildly different from a 3 or 4 star hotel. Felt completely out of place there right from our arrival.

We arrived as backpackers and walk to main gate where the gatekeeper was. He was shocked and stammered "You.. you walked here?". We were quite naive in thinking everybody did since there was foot path, but upon looking back, it was not paved or anything. Nearly every visitor had their own car and there was a shuttle to get you between the bungalows. We also got a welcome cocktail and complementary snacks on some tours. We found out that we didn't even have to carry our own luggage anywhere and of course there was dry-cleaning but it was at max 20$ / item.

A great experience, but we'll need another few years to save up for a similar experience.

I sometimes take the ICE from Arnhem to Utrecht. It's special, because it's an international train with sleeping cabins and sometimes even on-board catering. You usually have to pay an extra supplement, but not if you only ride it nationally. This kind of train only stops on three stations in the Netherlands (Armhem, Utrecht, Amsterdam), which makes it more special.

I got invited to some sort of literary award ceremony at the French embassy a few years back. I, uh, severely underdressed for the occasion. I got the invite for participating in the Albertine book store's bookclub, and for whatever reason, my brain went, "I can show up to this like I would dress for a bookclub session, it's the same people." Spoiler, it was not, and I really should have been at least in a button up and slacks, rather than my hoodie and jeans. As luck would have it, the gentleman who won the award, Emmanuel Dongala, was sat next to me during the speeches. I can still remember the look of "What the classless, American fuck is this guy doing?" as he took his seat next to me.

On the other hand, I went to my first opera at the NY Metropolitan Opera last year basically dressed the same way, and it was surprisingly entirely fine. Turns out, very few people want to be sat for hours in formal attire when hardly anyone can see you in the dark, anyway.

I went with a friend to Vegas. He was going to one of those super-posh conferences for his line of work, and just casually wanted to split the hotel bill (because he's cheap; the dude could afford to live in one of those hotels year round). At the end of the conference, all of his colleagues were throwing some party at the top of one of the hotels on the strip. He helped me through the security screen and we left the elevator. We went from a world of bright lights and gaudiness to dark passion and sultry beats where each seat at their reclined cushion alcoves was worth thousands of dollars. Prostitution may be illegal in Vegas, technically, but escorts that looked like world-famous supermodels (male and female, to be clear) were writhing across every lap at those recessed tables.

My friend got me to the balcony, where I got a picture of the entire strip at night. Then my friend casually mentioned that getting a drink would be about $1200 and we went back down to the normal floors for the free booze and $2 blackjack.

Never anything like that but my brother in law got tickets to a major league game close enough to see the umpires calls which is a big deal for me.

Spent a night at the Iceland Blue Lagoon Retreat hotel for a special occasion. It's like $1800 USD per night so it was a huge splurge. We saw Rebel Wilson staying at the hotel too. It was fancy AF.

Absolutely wasted if you only spend one day, but we couldn't afford 2.