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First and foremost, never ever try to pressure/push him into letting things out, or anything of the sort. Not attempting to throw accusations (tbh id probably be surprised if you do try that, but just making sure, cause ya never know) as that will only make him less comfortable with expressing what's bothering him and therefore harder to ever do it in the future: Now that's out of the way, my personal advice: I too struggle with expressing these sorts of things, but what helps me to do so is: Time/experience - the more he does it with you, he'll likely grow more comfortable and willing to do so, if he's anything like me ofc. This isn't something you can rush or make happen, you just have to wait for him to become more used to it and be patient


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