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Best friend from high school cut me loose after my divorce. We haven't had any contact in 20+ years. Not long ago I randomly ran across an obit where his mom died. Considered sending something to his dad since his folks were always nice to me. Probably should have done but I wussed out. Hope his dad is doing ok. Feels bad, man.
You can still send a "Hey thinking about you, thanks for being nice to me growing up.".
The second best time is right now and all that.
You're right, of course. It's kind of a can of worms, though.
And...dudes parent died. Screw the worms, that was over 20 years ago.