There are lot of gambler who doesn't have this aspect in their pipeline that one must not always win in gambling hence, the losing rate extremely high even higher than winning ratio which every gambler must experienced while gambling. But as you mentioned, when gambling with the soul purpose of having fun and gambling with the amount that can be riskable it could be very hard for you to have that feeling of lost while gambling because already you knew is a 50/50 game.
It is doubtful to hear that a player can enjoy losing, no one likes to lose, losing always brings disappointment, even if the bet amount is insignificant for the player. Another thing is if for a player gambling is a way to distract himself from other concerns, but this is definitely not entertainment, it is a search for stronger emotions, that can switch attention to something else, for a while. And those players who can earn money in gambling are very few, I think only a few percent of the total number of players.
Gambling is not a certain way of earning money but if you are that accurate with your measurement and with your prediction which is only limited to few games you could earn more while gambling but most players always put more efforts in accumulating much odds making it too difficult for them to win their bet. Of course anyone who is losing will not have that joy to continue gambling because they are losing their hand earned money but one thing that matters is that if they start winning they will definitely forget all they have lost because the winning ratio is above what they have lost.