Thank you.

He's going to shut it down initially so the best you can do is open a door, be warm and non-judgemental, and hope it's the start of something more.

"John, You've been on my mind so much these past few weeks so I wanted to give you a call. I know you've been struggling a lot and I'm worried it's getting the best of you. Is everything okay?"

"Yes it's fine"

"I just hate to see you having so much on your plate. Is there anything I can do to help"

"Nope. I'm good"

"Okay, if you insist. Just know I'm here if you do need something. I have a good listening ear or a place to get away if you just need a break sometime."

Talk how though? I don'tt really know what to say.

Send him and email stating all those things you listed and tell him that you're available to talk if/when he is. Then - and this is the important part - leave it alone.

I am the third child of 4 siblings. Complicated background, divorces, remarriages etc.
My brother is the oldest of the 4 of us at 33. I would say the last 2 or 3 years, but mainly this year he's been in a downward spiral. He drinks to much, he's hungover often and has gone to work hungover. He's involved in toxic relationships. He was engaged at the start of the year, but that ended due to his on foolishness.
3 weeks ago he crashed his car, he says it was because he was too tired and driving, but I wonder about that.
The simplest way I can describe it is like he's a frat boy.
Part of me thinks is that he's never dealt with our father's death. I am also suspicious of other underlying issues, but have no proof of those.
I have no idea how to reach out to him, without sounding judgmental but I'm worried. Very worried.