This is the kind of play I find most confusing. I personally don't like gambling (narratively or otherwise), but I grasp the general appeal. I struggle to understand what kind of appeal people are finding in gameplay built entirely out of meaningless decisions.
My best guess is that's it's an entirely character focused subset of gambling, combined with elements of performance; the player is gambling on the small personal question of whether their character can do X or knows Y, and/or is asking for the check as a very abridged way of performing "my character has trait Z" to the table.