There's nothing you can say, really, no magic words to take the pain away. The best thing you can say is “I’m sorry.” Just be ready to listen and care. Don’t try to convince your friend that everything is "fine" or that their loved one is "better off." Listen quietly and validate how painful and sad the loss has been.
People who are grieving don't expect – or even want – for you to take their grief away. It is enough just to listen. You cannot be expected to come up with 'solutions'. I think this is what people feel expected to provide, which is why they feel awkward around people who are grieving, as of course there is no 'solution' or magic fix.
Listening and really hearing what another person has to say is so important, and it’s not always easy. But, if you can: don't just do something – sit there. It can be hard to sit and listen to someone in intense pain or someone struggling with life and death issues, but just listening and being a witness can help more than any advice you could possibly give.
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