Have you noticed how hard it can be to say the right thing? Once when my elderly friend Margaret and I were discussing another (elderly) friend who had passed away, I made the mistake of saying, "She's in a better place." Margaret shot back with a matter-of-fact, "We hope so." All-righty.
Call it delayed maturity, but several decades later, I still can't tell that story without cracking up. You have to laugh at comments like that or they will eat you alive.
On a more poignant note ...
I gave up trying to say the right thing in 2006, when my friend Susie died unexpectedly. Following the memorial Mass, a small crowd of us drove to a country club, which happened to be near my childhood home. Here a private luncheon awaited us, thanks to Susie's oldest brother.
Throughout the meal, he and I did our best to boost each other's spirits the way we always had: by trading good-natured insults. "Put her meal on a separate check" and that sort of thing. I can't tell you how good it felt to laugh. But then it came time for the two of us to say goodbye. We stood awkwardly in the open hallway, staring at our shoes.
"I don't know what to say, Mark."
"There's nothing you can say."
Bingo. At first that statement stung a little—but then I realized it was just the reality. And in the words of Nathaniel Branden, "If reality could speak, it might say, 'It's nothing personal.'"
So when someone you care about is hurting, what do you do? Start simply by being there. Just acknowledge what the grieving person is going through. You don't need to use a lot of words.
Try instead to look for ways to pitch in. How easy is it to bring some comfort food, for example, or pick up water/coffee for the crowd? If it's someone you work with, you can offer to cover for them. Chances are, they'll let you.
Instead of saying, "If there's anything I can do," which tends to put more work on the grieving person's plate, ask, "What would be most helpful?" Don't be surprised by the simplicity of the response, or feel put off if there's no response.
Just let the other person talk—without interruption, value judgments, or the overlay of expectations. Grief is hard enough. Best to let each person express it in his or her own way, even when it makes no sense to you. If someone wants to cry or laugh or blast Bob Marley for that matter, why not just accept it?
Invite, but don't insist.
Along those lines, take nothing personally. If ever there was a time to not make it about us, this would be it. No grieving person should be made to feel responsible for lifting someone else's spirits. Give the person time to return to a sense of normalcy, even if normalcy has been radically redefined.
Even then, I don't think it's helpful to make every interaction about grief and loss. Allow yourself to relate the way you always have. Share good times. Share laughs. Let the person who's grieving share laughs. In this way you will help a hurting soul return to the land of the living. This side of eternity, what could be a better gift?