20 Not-Stupid Questions to Ask Your Kids over the Holidays


There is nothing like a holiday to bring people together. And once you’re together, you have to converse. There is a whole list of typical questions we ask our kids at some times: What’s your favorite subject in school? How are things going? But there is a subtle art to going deeper—to finding those brilliant cracks in their soul where the light slips in and enables us to have an illuminating conversation.

What made me think of this was a Huff Po blog I read over Thanksgiving about the trauma kids are experiencing when they get to college and realize they haven’t really thought about their future lives. They’ve been so fixated on reaching their goal of getting into college (or worse, their parents’ goal) that they don’t know who they are or what they want from life. This has led to a huge number of students suffering depression, with 50 percent of them reporting feeling hopelessness.

The blog recommends asking these three questions:

  1. Who tells us who we are?
  2. Where do we want to go with our lives?
  3. How do we want to get there?

Which are brilliant, but are slightly awkward at a family gathering. “Say, Missy, who tells us who we are?” “…Whaaaat?”

So I recently asked my teenage daughter and her college-age boyfriend (and my 8-year-old) to help me make a list of 20 questions that are both not stupid and ones kids wouldn’t mind being asked…

1.    Have you changed your look? In my family, we ask “What happened to your face?” as a kind of private joke between us… but the point is to observe, see, and ask questions about their appearance in a way that is positive and questioning, not judging.

2.    Are you in the mood to answer some questions? Because if they are totally not in the mood, there’s no need to provoke them further. Wait for a better time.  Like after they’ve eaten something. Although, kids who always say no to everything should not be listened to when they reject approaches. Those no’s are often a cry for attention and help.

3.    How have you changed most over the last year? If they make a stupid joke, laugh. At least they’re talking!

4.    What’s something you did this year that you didn’t expect to do? Be ready and willing to share things about yourself, too. Try to make your selections personal and interesting, not the same story you tell people all the time. That really annoys kids.

5.    At this time last year, did you expect to be where you are now? A twist on the pervious question. Probe a bit if you get any action on these questions. Think of these as like worms on a hook and you are trying to catch a fish—you want to reel them in to a real conversation.

6.    What do you think of Putin? If they don’t know who Putin is, there’s an interesting topic. But you can substitute any world leader or popular figure. Putin is just fun to talk about though. So is Tony Abbott.

7.    What color are you thinking of? Then try to guess, see if you get it right. This question was offered by my 8-year-old and makes a fun game.

8.    What do you think makes you you? A more conversational way of asking the first question from the Huff Po blog.

9.    Where are you headed next? Not just regionally, or like, to the mall…but intellectually, spiritually, philosophically. Take whatever answer you can get to this one.

10. What’s your next step? Maybe there is a way you can guide them.

11. Where would you love to travel to? Dreaming is free.

12. How would you describe yourself in a tweet (140 characters or less)? This is a fun one for anyone to play. Anyone who can count his or her characters, that is.

13. What’s the next thing you want to learn how to do? Ask yourself this one, too. I wanted to learn how to make Cheesy Potatoes, and I just did. They are in the oven now…

14. Which was the best of the movies you saw this year? Personally, I thought Belle was brilliant. Teenager says Guardians of the Galaxy. 8-year-old voted for Big Hero Six and added, “I’m done with Frozen. DONE!”

15. What was the most spontaneous thing you did this year? Well, if you haven’t done anything spontaneous, there’s still time.

16. What’s the best meal you’ve had recently? Cheesy Potatoes? If you are eating your mom’s food, maybe you should say hers…

17. What’s your New Year’s resolution? Or resolutions…

18. What’s your favorite holiday memory? Hopefully, there are some good ones.

19. What do you miss about your childhood? Hmmmm…

20. What DON’T you want for Christmas (substitute any holiday here)? If we are being honest, sometimes the holidays are made worse by getting things we don’t want. Can’t hurt to ask!

Happy Holidays!


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3 Responses to 20 Not-Stupid Questions to Ask Your Kids over the Holidays

  1. Donna in Delaware December 3, 2014 at 10:07 am #

    Thanks Maria. If I had kids, I would make this a conversation to have with them every 6 months. They somehow seem to change from day-to-day, month-to-month. You can ask these questions and more, stealthfully, or outright (with some kids, but you have to know your kids). Do it with love and attention though, children aren’t stupid! We need to see where are kid’s heads are. There are so many parents who know little or nothing about their children, and before you know it, the children fall into the had of others and get into trouble. This is a good post. Thank you.

  2. renee December 4, 2014 at 11:01 am #

    This prompted a memory for me, Maria. When the boys were in grade school – and maybe into middle school – we asked the inevitable (and lame) “How was school today?” question at dinner every night.

    Tired of the typical (and lame) “Good.” “Fine.” “The same.” answers every night, I followed up with “Tell us about something that happened today!” When I heard, “Nothing.” Not much.” or their equivalents, I finally said, ” Then make something up!”

    And from there, it was so much fun. They told us all kinds of insane stories … “… and then when the dragon walked into the room, we were really excited!” “We learned to fly off the school roof today during recess!” Stuff like that. Truly magical.

    Love your list!

  3. Alexa Fleckenstein M.D. December 5, 2014 at 9:55 pm #

    Great questions! Great suggestions!

    But … off the topic: Do we really need 14 new recipes for caramels, even if home-made?? They are but sugar and dairy – both inflammatory. How about doing a chutney? Baking gluten-free cookies?

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