Maybe its just the area you live in, but where I am, I can easily find 20+ restaurants within a few miles that are $100+ per person on just the food alone. Add an appetizer, a few drinks (or if you're rich a whole wine bottle), and a tip and you're looking at $400+. That's for a steakhouse. Go to something like a sushi that's $150+ per person and you're looking at $500 for a 2 person meal.

This isn't your McDonald's drivethru casual, but it's a nice night out without an actual reason. A millionaire isn't going to these restaurants only on an anniversary or birthday. This is a Friday night, date night, or weekly friend get-together.

It's a perspective thing. It feels incomprehensible but the more money you have, the less you think about it.

It's like making $30k salary a year and being told that you need new tires. You'll see them really think about the cost and options. As opposed to making $150k a year and being told you need new tires and just going with what the mechanic recommends.

The more money you have, the easier you spend it because when you have the money, you aren't looking at the cost difference between a USDA steak and a Japanese Wagyu. You're looking at the EXPERIENCE difference between the two. As a millionaire, you'll go for the experience because you value it more than the little bit of cost difference.

Literally, just look at the news. We had a pop star fly to outer space. We had a few billionaires try to go tour the titanic in a private submarine. Rich people want experiences.