"Weep with those who weep"

I am one of those who, in situations like this, is apt to say something  really stupid, or at least cliched [which embarrasses me just as much]. And I don't deal with sympathy very well either. Elizabeth Bernstein provides good advice:

How can you comfort someone grieving the death of a loved one? What can you say that might adequately offer solace? "I'm sorry" doesn't seem to cut it. ....

Here are some suggestions, culled from grief experts and people who have lost a loved one:

• Say something simple. "I am sorry to hear the news" will suffice at first. Then, on an ongoing basis, "I am thinking of you."
• Admit that you don't know what to say, says Ms. Walker, the grief educator.
• Don't ask, "What happened?" "You are making the grieving person relive pain," says Ms. White, who lost her husband.
• Don't launch into a detailed account of your loss of a loved one. "Give them just enough to let them know that you can relate," says Ms. Walker. "What you are trying to say is, 'I lost my mother, too. What is it like for you?' "
• Avoid clichés. That includes, "Good things come from bad," "What doesn't kill you makes you stronger" and "He's at peace now." Ms. Walker says they're "preachy, presumptuous and impersonal."
• Don't claim to know how the grieving person feels. You don't. Don't suggest that the mourner "move on." Stay away from words such as "ought," "should" and "need." You may want to say, "I can only imagine what you are going through."
• Follow the mourning family's lead regarding Facebook. Have they posted about the death? If they haven't, don't expose their grief. Should you decide to use Facebook, simply express condolences or share a memory. Do not discuss circumstances of the death.
• Keep your religious beliefs to yourself unless you are sure that the person you are trying to comfort shares them. (It is OK simply to say that you will keep the family in your prayers.)
• If you are reaching out or offering help, don't expect a response. Explain that you are checking in but understand that the mourner may not be able to get back to you and so you will call again.
• Promise to be there in the coming weeks and months. And keep your promise.

How to Express Sympathy to a Friend Grieving the Death of a Loved One - WSJ.com