The call came on a Sunday night, which is when these calls often come. A woman I’d met once at a Shabbos meal – quiet, polite, not someone who calls rabbis – was apologizing before she’d even said why she was calling.

“My father is in hospice,” she said. “He signed up with a cremation society years ago. He’s not religious, he never was, and he’s been very clear. I don’t even know why I’m calling you. I guess I just want to know, am I allowed to bring it up? Or is that a terrible thing to do to a dying man?”

I have been asked some version of that question many times, in hospital corridors, in prisons, at kitchen tables, and over the phone at hours when most people are asleep. And I want to begin where I began with her, because it is the most important thing I can tell you:

“Yes. You are allowed to bring it up. Not only allowed. If you are asking the question at all, it is probably because you love this person, and love is a perfectly good reason to have a hard conversation.”

In preparing this piece, I consulted on a forum with fellow Chabad rabbis around the world, colleagues who sit with families at these moments far more often than any of us would like, and I asked them to share their experiences. Several of their stories and insights have been woven into what follows.