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.