An Open Letter To My Family


An open letter to my family about why I ask so many questions


Dear Family,   

    You can’t imagine the pride and happiness that I have in seeing your successes and achievements in life. I know that pride is a feeling one usually has about their own achievements. But as your father and grandfather, I get deep pleasure and satisfaction in following all that you do.

     I suppose it’s pride I feel. But maybe it just makes me happy to see you building your lives as young adults. You are all so socially aware. I know you will make an impact in the world.

My grandson Ethan says that when I ask him questions it shows that I love him. Another grandson says my questions don’t bother him because he’s set and confident in what he’s doing. But there was that one time that someone suggested my questions felt like an interrogation.

It’s not an interrogation. I just love you.

First, of course, I am sorry. That was never my intent to put pressure on you by asking questions. Perhaps it’s aging. For me, time works a little differently. At 91, there’s an urgency to see things through to completion as quickly as possible. So I may ask about the same projects, things you are working on, more urgently. But that is about me. Not about any judgment of you what you are doing.

Please share, and please tell me.

So please share with me, and know my questions are out of love and a need to connect and to truly know you. That’s why I ask for copies of the papers you are writing in school, the name of the textbook you are using to teach that college course. And, that’s why sometimes I even bring “an agenda” with me to our Sunday brunch. I don’t want to forget anything you are doing, your interests, your world.

And, of course, you can always let me know if I ask questions about things you don’t want to talk about. The other thing about getting older is our filters fade away. There’s not enough time left to censor ourselves or worry about what others will think. We think. We say. Sorry!

Know that I love you and I need your connection.

familyYou have no idea how isolating and lonely getting older can be. Suddenly a quick trip to the grocery store or post office has become something to plan in advance. I don’t have all of the regular casual social interactions you have during the day. And, living alone, I am most often, that: alone.

You can blame me for the surge in participation awards.

Some complain that today’s youth have too many participation awards. In youth sports, it’s no longer about who won the game, but who showed up. Good job, we say! And maybe it was people like me who started that. Because to me everything you do is exciting.

  1. Ask them to tell a story

At least when my grandchildren were school-aged, opening with “tell me a story about…” rather than asking a direct question worked extremely well. For example, “tell me a story about school.”

  1. Ask open-ended questions

This is a good interviewer’s trick. Open-ended questions are those that can’t be answered with “yes” or “no.” “Did you have a good day at school?” or “did you have fun at your friend’s house?” are examples of this. “What did you do at your friend’s house?” would be an open-ended question. Or, catch them off-guard with something a little quirky—“What did you eat at your friend’s house?” That can get things started and take it from there.

  1. Understand that there may be things they don’t want to talk about

There may be times when your grandchild doesn’t want to talk or subjects they don’t want to talk about with you. Respect them when they tell you that. It’s important that they have someone to talk to when it’s not you. You might ask “do you have someone to talk to about it?” if you are concerned for them. If they say no, suggest a parent or teacher or someone that they trust. And reassure them, “I understand you don’t want to talk about this. But please know that I am always here for you if you do want to talk.”

About the Author, Jerry Witkovsky

Author of The Grandest Love and a long-time social work professional, grandparenting activist, and passionate grandpa, author Jerry Witkovsky offers fresh approaches to help grandparents enter their grandchild’s world, to leave values, not just valuables and create a living legacy.

Jerry shares more about the Grandparent-Grandchild Connection School Program and encourages grandparents to unleash their creativity and unique gifts to transform their family at



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