When grief comes to a friend, we sometimes avoid talking about it because nothing seems to measure up to the situation. Any attempt we make just feels trite and awkward. To complicate things further, grieving people tend to be awkward conversationalists. There are a lot of thoughts and feelings still unprocessed. Words may not flow easily.
In spite of all that, grieving people really need your expressions of kindness. Haunting many grieving people are thoughts like, “Nobody cares” or “I have nobody.” If you say nothing, those thoughts seem to be confirmed.
So, in my experience, here are a few good things you can say:
“I’m sorry. Do you want to talk about it?”
“I’m sorry. What was she like?”
“I’m sorry. Can I help with anything? Can I bring over some food?”
Cards and messages are also good. There is a reason they have stood the test of time.
On the other hand, it is possible to make hurtful mistakes. If someone has endured tragedy, quoting Romans 8:28 could cause pain and doubt, even though the intention is to comfort and build faith. Similarly, be careful about allusions to heaven if you did not know the deceased person well. It could imply that you would only love someone who shared your faith. You don’t want to mistakenly convey that their loved one is somehow less valuable.
Think of Job’s comforters. They started off theorizing about the reasons for Job’s tragedies (including blaming him) and brought no comfort whatsoever. Finally God intervened and comforted Job by giving him an encounter with Himself.
Similarly, 2 Corinthians 1:3,4 says:
Blessed be the God and Father of our Lord Jesus Christ, the Father of mercies and God of all comfort, who comforts us in all our affliction, so that we may be able to comfort those who are in any affliction, with the comfort with which we ourselves are comforted by God.
Note that it is not our shared experience of pain that necessarily equips us to comfort others. It’s whether or not we have been able to press through grief to truly encounter God. That experience of comfort will be what we have to offer to others.