"Is losing money really enjoyable?"
Funny
Very deep though.
To be honest, it is possible that very wealthy person could be gambling occasionally for fun. But am not sure if they do that with zero expectation of reward. Most fun things are quite addictive, that is why we are consume a lot of for stuff. So I wonder if a wealthy person who gambling for fun does that regularly or occasionally. The only reason he would gamble occasionally is if he has lots of other things that make him happy.
We should not stand in a negative perspective, look at a positive perspective, losing money to get back moments of fun and special feelings, which is an interesting thing, so sometimes you can't feel but other people can feel, lose money and what you can get back is quite interesting. But of course, sometimes losing money like that would be a happy thing, if losing money constantly for gambling, it would be a waste, even gambling addiction starts with such continuous losses, a lot of people have followed this trail