I fully support the premise, but it clearly ignores the reality. A man has to first be convinced that the environment around him will not reject him for crying, before expecting him to be vulnerable in such an unfamiliar way.
Will a crying man be deemed as someone unsuitable for being the emotional pillar in a relationship ?
Will a crying man be seen as someone who can't deal with crisis ?
Will a crying man be seen to be a child ?
No matter how much we tell someone it is alright, they won't believe it to be true until the environment shows it to be so. People talk about toxic masculinity as though it is a problem created only by men. But, the idea of it pervades throughout society. Affecting children, women and men alike. Men can't be the only ones battling it.
A comment pointed towards Khamenei crying at Soleimani's funeral as a sign towards encouraging men to cry. However, I only see it as an example for the contrary. Crying for men carries a weight, that implies that it must be reserved for an occasion special enough to warrant it. Had men crying at the death of their closest friend been customary, then Khamenei's voice cracking at the funeral would have never been reported as a special observation.