Toxic masculinity is real and I guess a big part of it comes from upbringing. I remember my grandmother always scolding me whenever I cried.
Boys don’t cry
A related story here: How do you help your friends go through a breakup? - #3 by Jaws but I think what really helps to get people to open up in general (not just men) is to ask two questions
- How does that make you feel?
- What else?
And don’t underestimate the power of “what else?” Each time I ask this question, it’s like peeling an onion layer by layer and ultimately you’ll get to the core of it.
One last tip I guess is to be comfortable with silence, men take a while to open up (myself included) so just be patient and have a drink while you wait. 