20 Questions for Your Kindergartner


Do you remember playing 20 Questions when you were younger? Did you also play this game in high school or college — maybe a R-rated version? The way 20 Questions works is that one person thinks of an object and the others playing can ask 20 questions to try to guess the object. The questions can only be answered with a “yes” or “no” and the objects of the game are to (1) guess what the object is and (2) guess the object by asking as few questions as possible. This is a great game for long road trips or situations where you and your kid have to wait for something. The basic version of the game is great to encourage kids to be curious.

My son just started kindergarten, which is bitter sweet.

On the one hand he is a big kid now and on the other hand HE IS A BIG KID NOW! He is asserting independence and learning things like how to navigate the lunch line, find his classroom, and be more responsible on his own. In the morning he gets out of the car with his oversized book bag and he is off. There are no extra kisses, no more hug, or the good-bye window. As he learns this much needed independence, I feel my heartstrings and connection to him grow tighter. Sometimes, I can literally feel distance growing between us. I want him to be independent AND at the same time I want to cultivate a continued close relationship with him. From a very early age, I have told my kid, “We don’t keep secrets. You can tell mom anything, even when it is hard. I will love you no matter what.” I know he hears me because he has said those words back to me on multiple occasions. He has even ratted himself out a few times by saying, “Mom, I know we don’t keep secrets and I did this thing…”

I have a different version of 20 Questions I have started playing with my kindergartner that changes the rules.

I use the game to ask open-ended questions about his day. The purpose is not to simply ask, “How was your day?” when I pick him up. Instead, I want to know more and to send the message that he can talk to mom about anything. The trick with my version of 20 Questions is to not barrage my son with so many questions that he has to go through a litany of events from the day. I like to ask questions that encourage more meaningful conversation so that I can gauge who he has relationships with, what was his mood throughout the day, what he enjoyed learning about that day, and what was challenging about the day. I do not literally ask 20 questions; I usually just ask one to three questions. 

Here is a list of 20 questions to ask to encourage conversation with a kindergartner:

  1. What was the funniest (most difficult, coolest, etc.) thing that happened in your day?

  2. What were the three best things about your day?

  3. If you could make a new rule at school that everyone would have to follow, what would it be? Why?

  4. If you could change a rule at school, what would it be? Why?

  5. What five words describe your teacher?

  6. What made you laugh today?

  7. Out of all the things you learned today, what was the most interesting? What can you teach mom from what you learned in school today?

  8. What do you wish you could do more of at school?

  9. What did you do today that helped a friend? Was it kind? Thoughtful?

  10. What is the hardest thing about being a kindergartner?

  11. What was the biggest decision you had to make today? Why was that such a big deal?

  12. If you got to choose who you sat by in class today, who would that be? Why? Who did you not want to sit by and why?

  13. Who did you sit next to at lunch today/play with on the playground? What did you talk about? What games did you play?

  14. What’s the biggest difference between preschool (your old school) and kindergarten (your new school)?

  15. What did your teacher read to you in school today?

  16. If you could choose any activity to do over today, what would it be? If you could plan the school schedule, what would you do all day?

  17. If I saw your teacher this week, what do you think she would tell me about you?

  18. Did you get called on by your teacher today? What did you get to do?

  19. What is something that your teacher said today?

  20. What are you looking forward to at school tomorrow/the rest of this week?

Right after school, my kid likes to chill and have a snack. Dinnertime is a good time for conversation and sometimes I wait and ask questions at bedtime during “pillow talk.” I don’t always ask questions that elicit deep thinking. A good bit of the time I ask my kid to tell me a joke of the day…

Knock, knock.

Who’s there?


Pencil who?

Forget about it. It’s pointless.


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