Not Trying to be disrespectful but genuinely wanting to somehow help...

We've been friends for a few months and we're surprisingly close & he's told me who he has a crush on, it's cute she has a crush on him too and yet I thought I was the only person who noticed this but yes everyone noticed it lol but I'm just not likely to ever bring things up...he's around six feet tall and just extremely lanky, prone to wearing baggy hoodies and jumpers even though he's very slight and he's always surprised everyone by how emotionally stable and weirdly understanding of everything he is and today he was acting funny at work which made everyone feel uneasy so I eventually tried to ask if he was alright and he broke down. And I had this assumption maybe because of his voice etc but anyway so he's on his period and it's apparently really painful and confusing for him because he has been going as a man since he was a teenager but he can't quite afford surgery yet...anyway that's not for me to share I'm just here to ask if anyone knows of any kind of pointers on how I can be idk supportive without seeming like I'm suddenly treating him better than usual just because this hunch I had turned out correct. I'm known for how self aware and aware of other people and how good at giving advice I am but I really don't want to lose an incredible friend and we really need to find excuses so he can keep on going for small naps when it gets too bad for him so he doesn't have to stand around with the rest of us....something to make sure he's not hounded by anyone or whatever.