[What a curious reaction to friend. Well, family was certainly better.]

I see. That explains the depth of your concern for him.

[His tone takes a bit of humor on.]

Perhaps a simpler phrasing is in order. You learn from your experiences. Your mistakes and successes. At least, one would hope you are open to the possibility of the unexpected. But I will leave you to your choices regardless.

[He probably won't respond again unless there's a direct question. But he at least would check for a response.]