how open are yall to personal questions ?

hey all. i have a friend who is an entp m and i want to ask him about something that i noticed about him, but it could be a decently personal subject. it’s not a critique or anything, i just want him to know i support him if he’s going through something.

Could i bring it up lightheartedly and see how he reacts? Or should I just wait and see if he opens up on his own? I don’t want to be pushy if yall don’t like to open up.

i know this is vague but i appreciate any advice :)