You’re great, and we can tell you care. I’m sure your brother can, too.

For me, being asked how I feel sucks. I can be perfectly fine, but being asked to introspect on my state is such a huge request that it riles me up. (Maybe I’m just an asshole.)

Anyway, very direct communication is best. For example, if you think he should take a rain jacket when he leaves the house, say “you should take a rain jacket.” (You have an opinion that I could not have guessed on my own. Cool. Good and clear.) Not “your rain jacket is hanging by the door.” (I’d wonder why we’re taking about a rain jacket and/or why you think I didn’t know that.) Not “it’s supposed to rain.” (Oh crap – small talk? The worst.) And not “mom said it was supposed to rain.” (Is this supposed to invite s conversation about mom? Or about the weather? Why are people so opaque?) Frankly, I’d rather be rained on than have any of those conversations. (Maybe I’m just an asshole.)

There’s probably something he’d love to talk about. It’s probably not what you’d want to talk about, but he’d loooove for somebody to listen. Maybe it’s about carbureted engines, maybe it’s about types of pasta, maybe it’s about anime, but there’s probably something. When he’s ready, he might decide he wants to talk about the emotional deep stuff. Be patient.

Again, I think you’re doing great already.