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Offer to take him out to eat at a nice restaurant. I just said , hey I know this is tough on you. “Let’s go and hang out. Don’t take anything and it’s all in me .”I’ve used this and I never had to say anything else. They know why you are doing it. I did it once a week for a month.I switched between subway sandwiches delivered to an actual outing.
I know people can sometimes get annoyed with others saying “I’m sorry,” about something terrible. It felt wrong to avoid it tho so I chose to also follow up with explaining why; that they were in this pain and experiencing the unfairness of life.
I did it in an awkward verbal-diarrhea kind of a way so I added that I cared about them and wanted to know they had support but had no clue how to go about expressing that.
I didn’t ace the delivery, but my message did get give them some degree of comfort.