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.

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.

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.

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.

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.

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 🤣

Got an extra legroom seat in the airplane by chance.

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 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.

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.

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.

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’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 aunt did hostile takeovers and her husband was even more rich. Their kitchen was bigger than my entire house. And that was their vacation house. I couldn’t appreciate most of it, I was just a kid. But I remember my cousin had a pool in his room.