European here. We used to spend a lot of time at our mansion in southern France and had 3 other places to crash back home in our country. My uncle had a few places, his wife did, other people we knew did(friends, friend's friends, etc.) and so on. I don't know what OP means with filthy rich. We could afford to have a plane but didn't own one except a small private plane.

Anyway, I met a guy once. In the beginnings of our relationship I was always amazed when my crush was invited over and kept telling me all this "magical stuff" about life that was hard to believe. It felt like he was fantasizing about some apocalyptic realm telling me what he has not had and how different it daily life was. As a guy in my teens I knew this and that about how different people live, but I generally didn't think about it the way you'd think I should have. I knew people were poor, but it never really got to me. It was like some laugh-it-off info that's not true. Anyways, we had him come with us a lot of times, I took him to places on days we didn't have school and it was just nice to see him smiling all the time. I didn't really get why but I was genuinely happy for him.

Now the embarrassing part. When it was time for me to visit his home for the first time to spend my vacation there I went without much cash and card's weren't that popular back then. I was invited for vacation, figured I wouldn't need much so I only took basic stuff with me. Of course I knew he wasn't well-off, but I didn't connect this to his housing situation and had no idea about the mistake i had made not taking any cash. After just a few days I grew frustrated because he didn't have anything i knew/needed home. They were normal people living off an average salary. I tried to put up with it and considering I told my dad I'd stay over I didn't wanna go home and look like an idiot, not like they'd care anyways. This is when I had realized what nightmare I walked into. You can laugh, but it was a traumatic experience. It was fun first and felt like a camping trip, just without the forest. Slowly, it started to annoy me. It was so sweet of him and his mom, they tried hard to make me feel comfortable and i didn't wanna come off as rude but this is when i realized how different we were. Being the sassy pussy that I am I cried in front of him(pity and self-pity) one night and decided to let go and talk about it, playing it all down a little bit so he woudn't be hurt. Solved with some talk and huggie huggie. So far so good. We had a great time the next weeks, I tried to be considerate, but I won't lie, it was the absolutely worst time of my life, so it felt at that time.

That's because I later ran away home with delusional ideas about how it would go, no contact with family until today. I've learned so much since then and I am used to it now, although I still can't lose the feeling that I "lost my water" if you get what I mean. It was damn hard, I went thru some shit, it made me the person I am and despite people telling me(back then when I was getting around a lot) to get off my horse I am ok ONLY because I kept being delusional and believing that I'll be fine. For a long time I kept occasionally feeling like I was suffocating(I still do sometimes) and there were a few times I was broken but I'm happy it went this way. Me and my crush reconnected 3 years ago, have been living together for the past 2 years and it's great so far. He's been a TREMENDOUS help these past few years. Despite the time I spent "getting around" I am still not "off my horse", but we're managing my whimsy self somehow. Our financial situation is ok and I'm fine except for my occasional paranoia. Still learning new things every day. I am certain if we didn't reconnect I'd be lost or contacting people I don't wanna contact because of how things went and how even today I still can't manage to do some basic things, hello clumsy me. Moral of the story, I didn't think my new normal would be this different. I'm happy for what we have now(that's actually a lie but contradictions are fine with humans if it makes them feel better) and moving on. Obviously playing it down and keeping it basic, but I just felt like writing off without much thinking, to say something.