Because I am a Clinical Psychologist, time spent with male friends can sometimes feel like a strange no-mans-land (excuse the pun). On the one hand, I try to encourage other men to talk about what happens inside their heads in order to build a genuine friendship. This also helps to avoid those scripted conversations that ban mentioning things with the slightest hint of perceived femininity (e.g. feelings).
On the other hand, I'm still a bloke and sometimes feel inexplicably compelled to engage in mocking, sarcasm and rigorous banter to uphold the male code of social behaviour. My personal opinion is that there needs to be a balance between the two; using humor to get through life's hurdles is a great skill, such as being able to laugh about your unfortunate facial features (e.g. having a nose the size of a yacht sail). But, whether you like it or not, all men experience strong emotions, feel weak, get scared at times etc. This is where you need mates who will get behind in support, tell you its OK to feel sub-par, and lend a hand to help improve your situation. Denying this reality is simply a dumb (but understandably common) strategy that, in the long-run, will make life worse for you and the people you care about.
The problem here is that 'doing masculinity' or 'being a man' happens, in part, through your behaviour within friendships. There is a belief that men are able to display traditional masculine traits by avoiding emotional expression and focusing on common interests and/or physical activities with other men (Migliaccio, 2009). For me, I picture this idea as men being on a friendship stage where your role is that of the hard-as-nails bloke in the day's feature performance (think that metaphor may come back to haunt me). "Scared?! What are you, nuts? I drink engine oil for breakfast buddy."
So, the big question here is how do you promote friendships that de-emphasises a water-tight masculine 'performance' and instead promote a more reality-based view of men's lives; the one where inevitable periods of psychological strife are allowed to be acknowledged and talked about? I would imagine that I would be too scared to talk about anything other than acceptable male conversational topics had I not trained in the profession I now work in. In effect, I have become well-practiced or 'desensitised' in having previously tough discussions (with both men and women). Aside from the strong societal pressure to conform to gender (and other) norms, never having got into the practice of talking openly to others about unpleasant aspects of our inner lives represents a key barrier to opening up.
Form a support team
Our lives are full of sub-cultures where all sorts of rules around accepted social behaviour are formed and maintained. There is nothing stopping you from creating one whereby it's OK to be open about your psychological functioning. The trick is to find a couple of people who are wanting to do the same thing. This way, you are not trying to change the whole world's view on expected male behaviour, but you are creating a little sub-culture of manly support.
Perhaps you have male friends whom you have opened up to in the past. Provided this went well for both sides, this would be an obvious place to start. Otherwise, you can try experimenting in small (and hopefully low-risk) ways. You can do this by dropping little 'disclosure invitations' into a conversation (could be another regrettably-worded phrase there, but hopefully you get the drift). For example, you could reveal to a friend that work gets stressful for you at times, then ask how often he himself finds work stressful. Hopefully this would get the conversational ball rolling. If you feel more confident, you could rip right into the funny how men's friendships can be more restricted than a mankini topic (be prepared to see disturbing images if you Google that word). Just be careful though, you want to maximise the chances of a positive result with these efforts, so think about the pro's and con's of leaping into the deep end of the 'genuine conversational waters'.
Work on it
I got more comfortable talking about people's emotions, life challenges etc. by doing it regularly. This represents an actual skill you need to develop, just like it is a skill to sink a 6-foot putt with your opponent trying to distract you with an orangutang impersonation (with his shirt off and riding the flag stick like its a scud missile). While practice will not make perfect in this arena, it should at least make you a more comfortable talker (and a better listener). Don't worry Mr compulsive fix-it guy, we don't need to try and solve all of life's problems, we just need to be supportive to our friends and avoid perpetuating this stupid idea that people should be stone walls of stoicism.
The bottom line
Opening up can be a risk, but also opens the potential for better, more genuine relationships. Thinking you can walk about life showing no emotion or weakness is not how reality works. Sooner or later, this strategy will go pear-shaped. Men may keep it stoic in same-sex friendships because there is often pressure to conform to the gender norms. But, being able to step out from this conformity treadmill can bring a host of potential benefits to yourself and others.
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