Most Helpful Guys
1. Men learn at a very young age that they are to be strong and tough and to "suck it up" and not whine about their woes.
2. Men are not used to being vulnerable - really ever - and sharing our feelings makes us vulnerable, and that's scary and too often is used against us - if not immediately, then later.
3. Nothing dries up a vagina like a whiny man.
Men have to have a tremendous amount of trust in a woman (almost always one single woman) in order to share his deep emotions, and she has to earn that trust over time. And many women simply aren't trustworthy, and others who might be don't invest the time and effort necessary to build that trust.
"Because no one cares about how men feel and it's girly to feel". When you grow up as male and you have the past generations basically telling you to man up if you get hurt and start to cry, to hold in the tears, to be tough... it really beats down a lot of men and they grow up emotionally reserved. I wasn't like that growing up. I was naturally emotionally reserved. I've always relied on reasoning because my emotions have gotten me into trouble more so than help me. I also repress them so I've never truly understood my emotions or feelings so it's hard to express something you don't comprehend.
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Most Helpful Girl
Because, for one, some people call them pussies for doing so, and secondly, because unlike women in this day in age, it isn't as encouraged or supported by society by means of social/political correctness and resources.