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Fun is not in losing, fun is in the process and in winning.
It's a bit strange to say: I'm happy even if I lose a lot, unless the gambler is really looking for entertainment in gambling instead of money.
Have you played football? When you play football, you run, get exhausted but you still have fun, you have even more fun when you win the match but sometimes you lose too. Even if you are not a good player and you lose football matches frequently, that still doesn't make football annoying, it's still enjoyable. Gambling is like that, you can still get fun even if you lose but everything depends on you, you shouldn't lose more than what you can afford to lose. If your pocket doesn't give you the ability to gamble, then you can play with play money.
The average gambler never feels happy when he loses. They know losing and winning are part of the game, but most gamblers only feel happy when they win a bet. Maybe they feel fine when they lose, but chances are that the gambler is not the typical gambler who gambles for money. They are responsible gamblers and do not mind winning or losing.
I'm not sure someone who comes to a gambling platform with his hard-earned money of $1000 feels happy about losing after betting, maybe it would be worse and feel more angry if the money came from a loan or something like that.