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.

I got the chance to visit the penthouse at the top of the Chrystler building. The guy opened the topmost windows and let me partly hang out of it for a photo (I have to dig it up though)

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.

Not work related, but I used to do pickup games with the players on the best Tribes Ascend team in the world every day!

My dad once told me how he won a bunch of money betting on a horse race and spent it all that night in the fancy suite type area that overlooked the racetrack.

I ate dinner in NYC at the penthouse fancy restaurant of some five star hotel. I could barely eat I was so intimidated. The food at that time was for some reason having a trend of "foams", which is this weird thing where it was like lobster with a side of foamy stuff. I never understood how that was food, but the restaurant by itself was incredible.

I grew up very poor, but my mom's childhood friend was well off and had rich friends. I would stay with him a lot so his kid and I were like family to each other. A rich "daddy's girl" friend of his, who I had only met once or twice before, apparently had a crush on me and sent me a formal invite to her quinceañera (sorry if misspelled) with all expenses paid. On the weekend of the party they had a black car pick me up from school (Friday after last bell). It drove me to a shop where I was fitted for a suit, then a stylist for a haircut and my first manicure, then taken back home. The next morning (Saturday) I was picked up from home and taken to the local airport where a private jet was waiting for me and the new suit was already in its coat closet. I was flown to Miami and put up in what seemed like a really nice hotel. The party was glitz. Everyone, including myself, was wearing something that cost thousands of dollars. Definitely no rented suits there. The next day, I was flown and driven back home. After going through all of that, I spent literally five seconds with the birthday girl during the party before she was whisked away and I didn't see her again.
¯\_(ツ)_/¯

It was a surreal experience.

EDIT: As an adult I have had many situations that qualify for this post, but I never felt as out of place as I did that one time.

Business class flight to Japan. I’m just some engineer in a rural factory and was headed to some rural factories, but damn was the trip fancy. As we landed my coworker had to explain that the booze was free.

It was definitely a wild journey

Please tell us what your list of crazy things was. Lol