Questions to Ask Your Adult Child Before Your Grandchild Is Born

This guest post is by Jerry Witkovsky, MSW, a proud grandpa to six grandchildren ages 13 to 33 and the author of The Grandest Love: Inspiring the Grandparent-Grandchild Connection. Jerry is a grandparenting ‘activist,’ speaking across the country, setting up Grandparent Connection programs at area schools and being featured on radio, TV and in the news.

If you asked me a year ago if I would ever keep a secret with my grandchild at the expense of my adult child, I would have said, “absolutely not under any circumstance!” But as I met and spoke with other grandparents I heard a lot of pushback from grandparents who were desperate to connect with their grandchildren, to stay connected to them as they aged.

“How can I build a special bond if my grandkids can’t trust me?” they asked.

I heard their concerns but realized that long-term trust across all of the generations must be transparent. Grandparents want to establish trust with grandchildren, but don’t want to jeopardize trust with their adult children. Speaking of trust and honesty, my thoughts spiraled … what other values did I want to share with my grandchildren? And what did my adult children want and expect from me as a grandparent and as their parent?

Conversations with adult children about their children can be so charged at the moment. If I ask them about great vegetarian recipes after their child has just visited, they may interpret that as my questioning their choices, or worse, that I snuck some meat into the menu! And the trust question, after a sleepover with their 10-year old, will certainly elicit a panicked “Oh my god what’s wrong what did they tell you?”

That’s why I say asking while they are still pregnant before the first grandchild is even born, is the best time to have these conversations. They’re safe, they’re hypothetical and they open the door for easier conversations down the road, as in ”Remember that time you asked me about …. well, I’d love to talk about it now.”

Here are some questions or desires I wish I had said or asked my children while they were pregnant before little pumpkin even hit the scene.

On being a first-time grandparent

  • Just as you are having a first time experience as a mom (or dad,) we too want to be best grandparents in the world.


  • What things do you want us to have in our home when Jilly visits?
  • Is it okay to give her candy? Or cake? Or Ice Cream, or to introduce new foods? If there are dietary restrictions, please be sure to tell us.


  • If you need to call at 3 am because spots have appeared all over the baby’s body (yes, that is normal) that’s okay—thinking of things that are not for the doctor, but helpful tips for you to know.
  • Can we tell you what we are thinking?
  • If we are nearby can we stop by unplanned?


  • If Timmy says “don’t tell my parents but …” how do you want me to respond? (I was surprised in my own case that my daughter-in-law said a tattoo was okay to keep a secret. She did want to know if her child was in danger or doing self-harm).
  • Your career is so important to you. What can we do to support you to get back into the workforce after the baby is here?
  • We’d appreciate your feedback on us as grandparents.
  • What do you want from us as grandparents?
  • What values do you want us to teach your child?
  • Is it okay for us to set up a college fund for your child?

I knew that I wanted to set aside a sum of money at my grandchild’s birth to put into an interest bearing education fund. The child’s parents would be the guardian on the account, but the money would be my new grandchild’s. We would hope that it would be welcomed as an expression of our love but were concerned it might be perceived as us thinking they couldn’t provide for their own child.

For interfaith families where the child is being raised in a religion other than yours

  • How can I support and be involved in the upbringing of my grandchild?
  • Will our cultural traditions be off-limits?
  • Can my grandchildren celebrate religious holidays at our house, even if they are raised in the other religion?
  • Can we teach each other about our respective religious faiths?

For connecting to “the other” grandparents

  • How do you want us to connect to your spouse’s parents, the “other” grandparents?

For example, when we started the education fund we didn’t want to it be perceived as “competition” with the other grandparents, which can happen if their means are different. In fact, I wanted them to know in case they wanted to contribute as well.

  • Do you want us to connect with them on bigger ticket birthday gifts — like if we are getting them a bicycle or laptop and perhaps the other grandparents were thinking of clothes? So the gift can be from the grandparents collectively?

For staying connected to our own adult children.

  • How will we maintain our relationship with each other?
  • Can we still have one-on-one time with each of you?
    My wife and I hoped to not lose our relationship with our adult children once the grandchildren came. I knew I wanted time with my daughter, and enjoyed one-on-one time with her spouse as well. It may seem like there’s never enough time to go around for everyone, but in talking about it, we would figure out how to make it work—including using Skype, texting or other technology, especially when we are in different cities.
  • I’d like to have this same conversation with your spouse. Is that okay?


  • We would love to babysit little tiger. Would you prefer in our house or yours?
  • We would never want to be paid for babysitting, but would love a thank you or to know that it’s appreciated (this conversation may be different for different families.)
  • You may even want us to come and babysit when you are home, just for you to have time for a bath or a nap!


  • Is there anything we did in raising you, good or crummy, that you would like to replicate or avoid (this one may not be good in all cases, as it could open a Pandora’s Box, but it also may be a time for healing and connecting with your own adult children.)
  • If you have any financial issues, please let us know (or perhaps you as a grandparent can lay out if/when/how you would help.)
  • We want the grandchild to go to this specific camp, private school, etc. (or we would be willing to contribute if your child goes to this camp, school, etc.—this could be considered as too imposing, but if you know you feel this way, you might want to get it out early.)

Why should grandparents ask now?

You are putting yourself and your feelings into the world, knowing that the response from your child at the moment might be “what are you talking about? I have to get a crib and a car seat right now!”

You can’t control how others will respond to your feelings, but you’ve put them out there. If your heart is pure and your intentions are good—then say it—put it out into the Universe. Ask them their preference. Don’t assume anything and don’t be afraid to take the risk of sharing.

The conversation is not just about trust, but a chance to share your desires as a grandparent and to offer to be there for my children as well. I know this is a special time first and foremost for them, but as with any “tender loving communication,” it is multi-dimensional and important to me as well.

While there may not be a response to my ideas at the moment given, at least I have opened a door and created an atmosphere for the future. My daughter the social worker has been known to respond “I know you. I know it’s important to you, but I don’t want to talk about it now.”

But at least I have laid the groundwork for real life situations and invited conversations that I know will be a part of our lives.


Some Kudos We've Received

Scroll to Top