Maybe bring up some sadness you yourself have had of late, not the same kind they are going thru, but let them know that you are available if they want to talk about their sadness. Most times people will grab hold of a chance to talk, to open up. So many people suffer from lack of anybody to hold on to when they are sad. Its not easy to be smiling all the time and "brave" when things go south, but some kind words might mean the world to somebody, but you have to make a connection with them to they see somebody cares.
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He was not happy. And even if someone asked him that, they could not help him. We are all responsible for our own happiness.🙏 Whatever that is to you.