Conversations With Kids- 5 Conversation Starters


Every day during the school year I excitedly pick up my son from school and cannot wait to hear about his day. “How was your day?” or “What did you learn at school today?” are common questions I innocently, and enthusiastically ask. He doesn’t match my enthusiasm with responses like, “Good, I guess.” or “Um, fine?” or the dreaded non verbal answer of a shrug. He seems thoroughly annoyed when I ask. I remember when he was in kindergarten I asked the “How was your day?” question and his response was a looooonnnng sigh, with the reply of “Can you not ask me any questions today?” Let’s face it, it’s hard to have conversations with kids sometimes.

It actually hurt my feelings, as silly as that sounds. He wasn’t even rude or disrespectful in his tone, he was just tired. Tired of being in a classroom all day where he was told what to do, tired of answering the 50 questions he was asked at school, and just emotionally tapped out. Also, he is a boy, and let’s face it: boys usually don’t care to share details about their day. 

I took my hurt feelings and just resigned to lonely car rides home after school every day for a few weeks until I had an epiphany. What if I was just asking the wrong questions? So, I tried a new approach. 

After picking him up from school I tried something new. Instead of “How was your day?” I experimented with some challenges like “Bet ya can’t read the next billboard we drive by.” Or, “Do you think you can count how many red cars we pass?” He likes challenges and felt this was a bit of a game, so he was engaged. Over time my questions and challenges changed and I found a really good groove for our after school drive home. 

Mom and daughter walking, holding hands. Daughter wears a yellow shirt and has a backpack. Mom has on a white shirt and light brown crossbody purse. They are holding hands and talkingWhat was really exciting about this was that after he answered my alternative questions or completed the challenges we did together, he would just start naturally opening up on his own. After a few minutes of some “fun” questions, he would randomly state “Oh did you know that my teacher took us to the library today?” or “Guess what Olivia did in class today?” He just started sharing on his own! Now, I won’t lie: this was a slow process, BUT well worth it! 

If you are looking for ways to bond with your kiddo on your ride home from school, or maybe ways to get your family more engaged in conversations at the dinner table, here are a few ideas for some “fun” questions to ask or challenges to change the family dynamics and have conversations with kids: 

  • Would You Rather” Questions-  “Would you rather have a robot that does all your chores or a robot that does all your school projects?” These types of questions are GREAT convo starters, can help you learn more about your kiddos, and generate some laughs! This is the book I got to help me come up with some fun questions on the ride home after school. You can even have your kids read some of the questions to you and each other on the drive home or at dinner! Hello, MOM WIN if you can get your kid to read!
  • “Challenges” – Create mini challenges for kids. They love arguing, no matter the age! They love proving parents wrong….so give them the chance! Ask things like: 
    • “I bet you can’t find 10 red cars before we arrive home.”
    • “There is NO way you will be able to hold your breath at this stop light until it turns green.”
    • For teens, maybe try, “I will give you a dollar if you can give the official name of the next song on the radio.” (Really challenge them by playing an “oldies” station!)
  • “Hypothetical” Questions- This is a great family fun question because it is cool to see how different each child is, and they love hearing parents’ answers to these questions too! Try a few like this: 
    • “If you won the lottery, what is the first thing you would buy and why?”
    • “If you could be an animal, what kind would you be and why?”
  • “Top Five” Lists- Ask them what their FAV things are. They love talking about themselves, so this is a great way to start conversations. Not only could you learn something new about them while you have conversations with kids, this could inspire some gift ideas, dinner ideas, party themes, or vacay ideas. Some ideas…
    • “What are your top 5 fav songs?”
    • “Share your top 5 least fav foods.” 
    • “Where are your top 5 dream vacation destinations?”
  • “Nosey” Questions– This is a sneaky way to learn about your kids’ friends and teachers. I like this one a lot because your kids have no idea they are actually telling you information about their day or life at school. They tend to accidentally reveal more than you even ask! I am always careful to redirect answers that could sound like “trash” talk or lead to bullying though. Adjust the questions according to grade/age, of course. 
    • “Of all the classmates in your class, which one is most likely to finish lunch first?”
    • “What is the most boring assignment a teacher ever gave you?” Kids love to complain, so open with this, then add, “Ok, now what was the most interesting assignment a teacher ever assigned?”
    • “What is the grossest school lunch you ever had?” (Again, they LOVE complaining! So start there and guide to some positive questions).

I cannot say I am a pro at this whole mom gig, but I have found some successful ways to engage my child in conversations that don’t result in as many shrugs and sighs, or “I dunno, I guess” answers. The added benefit is that these types of conversations with kids tend to transition into them telling you about their day or some random fact about a peer from school. If nothing else, it creates an atmosphere that encourages kids to be more receptive if you do directly ask questions about their day, and best of all: sometimes it just allows you to have some fun together.