According to many bereaved individuals, it's appropriate to reach out to the bereaved, no matter how long it's been. The bereaved never "get over" missing their loved ones and they appreciate knowing that you are remembering them too. This was the dilemma a friend found herself in.
My friend has two daughters who both became physicians. They were each influenced by their family physician and many years later, my friend wanted to reach out and let him know what a pivotal role he played in her children’s lives. She began by researching his current address and in doing so learned that his 50 year-old daughter had died. She wondered how she could write her intended letter as well as express her sympathy for this tragic loss. Here is the letter we came up with:
Dear Dr. Smith,
I recently learned that your daughter Jane had died and I wanted to express my deepest condolences. We’ve had such a long relationship with you and I remember Jane with fondness. It’s been many years since we’ve been in touch and I’ve thought of you often over the years. Both of my sons have become physicians. It was the caring relationship they had with you as their doctor that initially sparked their interest. You had a profound and positive influence on them and our family and I wanted you to know how grateful we are to have had you in our lives.