20 Questions to Ask Your Teenager Instead of “How Was School?”

February 29, 2024 in Modern Motherhood - 1 Comment

When Callie was younger, she was always super eager to share the highlights of her day at school—spilling to me about who needed a bandaid because they fell down, who got in trouble, or who accidently peed their pants. But now I feel like I’m constantly digging a little bit deeper for details about her day, which I think is natural because she’s a teenager. Even though I’m so excited to talk to her after pick-up, often the car ride home from school is pretty quiet as she decompresses. Asking her “how was your day?” or “how was school?” doesn’t elicit much conversation.

At all.

Or I get a tired “Fine.”

I get it. She’s  been around other people all day and probably wants a little time to be by herself. I’ve found the best information usually comes out later at dinnertime or as we snuggle before bed.

As parents, I think we’re so eager to hear about their days because we’ve missed them (of course), but we really want to quiet our own underlying worries when our teens aren’t in our care. We want to know whether they felt safe, were happy, acted like a good friend, and were treated as a good friend by their peers. Plus, it’s fun to get a peek into their new experiences and new learnings.

To help, I cultivated a list of 27 questions to ask your  teenagers instead of “how was your day?” Check out these conversation-starters below! 

On Friendships

1. Who made you laugh today?

2. Who was in your group today?

3. Who did you sit by at lunch?

4. Is there someone you want to be friends with but aren’t yet?

5. Who did you hang out with most today?

6. Was anyone sitting by themselves today? Who?

7. What do you like about “X” friends (whoever they talk about most)?

On Feelings

8. Did anything make you feel happy today?

9. Did anything make you feel sad today?

10. Tell me about one thing you did today made you feel proud (and why it made you feel that way).

11. Did anything make you feel worried or uncomfortable today?

On Learning

12. Tell me something you know today that you didn’t know yesterday.

13. What do you wish you learned today?

14. Can you teach me something you learned?

15. Tell me about a story you read/listened to.

16. Describe something that made you curious today.

17. What was the most challenging thing you did today?

On Classroom Dynamics

18. What made your teacher smile today?

19. Did you see anyone being kind/unkind today?

20. What was the most surprising thing that happened today?

21. Did you see somebody who needed help today? What happened?

22. What would you change about today if you could?

23. What did you  do today that you enjoyed?

24. What did you create today?

25. Tell me about one thing you did today that you didn’t enjoy.

26. Tell me about XX (insert subject your child’s teacher has shared with you).

27. What are you most looking forward to tomorrow?

 

If 27 questions to ask kids instead of “how was your day?” seem like too many to remember, many of my mom friends just use two simple questions every day:

What was your favorite part of the day and least favorite part of the day?

Otherwise known as the good and the bad, the high and the low, or the rose and the thorn. The answers will likely tell you everything you really need to know and hopefully reveal more than just who peed their pants.

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Jaime

Jaime is a writer, editor, and lifestyle storyteller focused on modern womanhood, slow living, and life after survival mode. As the founder of The Wildflower Edit, she creates thoughtful, beautifully honest content at the intersection of motherhood, disability, emotional healing, and intentional living. Her work invites women to edit their lives with care — keeping what feels true and releasing the rest — for anyone learning to bloom in their own way.

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    For the women blooming in unexpected places…..

    For the women blooming in unexpected places…..

    Hi Y'all

    Hi, I’m Jaime — writer, mother, storyteller, and the heart behind The Wildflower Edit. For nearly a decade, I wrote online as The Princess and the Prosthetic, sharing my daughter’s journey with disability and the lessons our family learned along the way. It was a beautiful season — full of advocacy, connection, and community — but as my daughter grew older, I felt a shift. She deserved more autonomy. More privacy. More room to decide how she shows up in the world. And I realized something else: My own story was expanding too. Motherhood was still here. Disability was still here. But so were grief, healing, womanhood, nervous system care, feminine energy, homemaking, identity, softness… the fuller, deeper pieces of life that were ready to be spoken aloud. Whether you come for the cozy routines, the motherhood reflections, the disability advocacy, or the soft life inspiration — thank you for choosing to share this space with me. Pour a warm drink. Settle in. Let’s grow a life that feels like you again.

    Jaime

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