Always Walk into, Not Away from, People’s Grief

This is something that the church needs a better job teaching. From my personal experience you have three groups,

1. Those who don't know what to say, so they avoid
2. Those who aren't sure what to say and often say the wrong thing
3. Those who have been through grief and come alongside someone

I would say from my experience 95% of the time, someone in grief, just needs someone to come alongside them. You don't need to talk about the grief. You just need to talk and engage. It is as simple as that.

Those of us in your group 1 most of the time avoid because we don’t want to be those in group 2 who “often say the wrong thing.” And we have many times heard bitter words from someone in pain who says flat out that we can’t understand, and that our words (no matter how well-intentioned) are painful.

All of us have experienced one or more types of grief, but even when it’s exactly the same situation (e.g. both lost a parent), you can still never know exactly what the other person is feeling. If the loss is different (say, lost of spouse vs. loss of a child), then while you can talk about God’s healing from that loss, the situations are still different enough that saying the wrong thing becomes much more likely.

As far as your point about just needing to talk and engage, that’s usually what I try, though very carefully. It feels very inadequate though (and kind of like avoiding), even if that’s what the grieving person wants (and not all, in my experience want interaction, at least not right away). I’m sure extroverts are better at this, but for us introverts, it’s difficult to know how to handle this, particularly when it’s different for each person. I’m still not sure in which cases it’s better to risk offense than to avoid, and that is probably also different for each person you want to help.