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polymathwannabe comments on Open Thread, January 4-10, 2016 - Less Wrong Discussion
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Overcoming fear is always healthy, but you should not let social expectations dictate how you have to feel. There's no single way how men are supposed to behave. Trying to force masculinity to fit inside a rigid box of allowed behaviors is a recipe for frustration and self-hatred. If you have feelings of vulnerability and fear, rather than denying or repressing them, you can observe and understand them.
In cases like this I always recommend the Empty Closets forum. Members are knowledgeable and compassionate.
Just a sidenote: there are multiple "boxes" for masculinity, and when someone tells you to get out of the box, they often have an alternative box ready for you. (For example, instead of constant checking whether something you want to do is not "girly" or not "gay", they may offer you to constantly check your "privilege".) Remember that you can avoid those new boxes too.