Whether or not that was a shit test, the point here seems to be how comfortable one is in his own skin, self knowledge.
Leo's approach is "brutal force": trial an error unitl you get it (btw I appreciated his last two videos about how to get laid). Defintely useful, but not necessarily the most effective, efficient, or precise. Also, not very compassionate towards yourself in the sense that it is lacking self-love. That will eventually back fire sooner or later.
Not effective because it will probably work eventually but results can be temporary because, although you can now master the external reality, your internal reality has not been necessarily addressed and healed.
Not efficient because it can take really ages and as such a lot of resources (money and time) that most people don't have unfortunately.
Not precise because it does not address the root cause, which is in your interiority, i.e. lack of self knowledge.