I remember I rarely cried as a teen. On one of the rare occasions I did (I was stressed about school), my dad told me to suck it up and would periodically tease me about it for months afterward. My mom, meanwhile, told me verbally it was ok to cry, but if I ever actually tried to come to her to vent about anything, she would brush me off immediately.
Cut to well over a decade later, living on my own, it's really helpful to cry. Unfortunately we live in a culture where if you, as a man, cry in front of others, you're likely to lose respect even if you're literally in mourning. I teared up when the whole thing with Angella happened in She-Ra, I wept for hours when Trump got elected again. I cried on and off for a long time after my best friend of over 15 years ghosted me out of nowhere, but it was always alone (except for once, which I deeply regret. That's a long story but it did reinforce what I'm saying).
If another man came to me to cry about something, I wouldn't want to discourage him, but I'm not sure I would even know how to react.