Not crying because of expectations is the kind of idea that tells a person, regardless of gender, that people's idea of them crying is bad and in order to be loved you should not cry. This is because kids think they're the center of the world. This is important when thinking about child pyscology. If you tell your son to keep it together when he's about to cry you're telling him, "if you cry I'll love you less." Obviously if he starts to cry start to work out the logic on how to make the situation better. That's what men do best. You can teach them how to figure out their problems from there because you've allowed them the space to show their emotions. If you want to grow a child into a man, let him make his own decisions, even when to cry. There's more power in owning your emotions than hiding them, because hiding them is a form of fear. There's no moral stance taken here. This can all be summed up as "Do as thou wilt."