I believe you're imagining a scenario where there isn't much of a skill gap, e.g. a match between a newbie and a competent amateur; a competent amateur and a professional; or a professional and a grandmaster. Losing to someone who's still "within your sight" can still be fun, because there's still an element of challenge to the game, and there are still stakes—i.e. you can still control how badly you lose, and therefore there's still something to strive for (to lose by a smaller margin.)

But when your level of skill gap with another player is too large, such that you won't learn anything by playing them and the entire match will be under their control 100% of the time, then there really isn't any point in playing them, and you'd be far better off—both for your enjoyment, and for your growth—to play against a weaker player.

It might be fun to have a sprinting match against your local state champion. It might even be fun to have a sprinting match against Usain Bolt. But there's no point to having a hypothetical sprinting match against The Flash. You wouldn't even leave the starting line before he crosses the finish line. There's no gradation of success available to you. You're simply crushed.

Likewise, there's no point, if you're a five-year-old, to trying to (seriously) arm-wrestle an adult. Your undeveloped strength will be overwhelmed without accomplishing the slightest movement of the opponent's arm, right at the beginning of the match, every time. You won't even get to practice the skill or build the muscles involved in arm-wrestling.