As for the death of loved one, my grandmother's 3 sons, myself, and a few other close relatives stayed by her side during her last hours. She continued to fade, so we asked if she wanted her favorite drink, a martini. She raised her frail arm strapped with tubes and monitors. With a bony "thumbs up!" she punctuated her exit from this world. Her urn sits above her desk at her and my dad's old business to this day. It reads "Ashes of Problem Employees" (see photo).
As for the question, context and tact would be the best criteria to determine when and with who, but not so much what, we can joke about.