So two things happened this week that have led to this post.
One, I have come to accept that this holiday will be far different from what we have known and loved. There won’t be the usual big and loud family gatherings with people piled into a house to celebrate Christmas. Instead, there will be lots of our own family time. Just the four of us. Together. By ourselves. For two weeks.
Two, I was sorting through some old teaching resources and getting rid of things I don’t need anymore and I came across some of my old ice breakers and conversation starters that I used to use with my students. I always found that students were much more receptive to learning how to solve equations if we’d spent a bit of time doing some fun activities at the start of class! Anyway, I was about to toss the pages into my recycling pile but then thought twice about it. I knew there was some good stuff in there I could maybe use with my own kids.
So what do these two things have in common? Well, it turns out that I have 100 conversation starters that are good to use with kids, tween and teens. Since the four of us will be spending a lot of time together this holiday season, they may just come in handy.
Conversation Starters in a Jar
So, what is my plan? Well, so far, I have typed them up (my current copies are a bit all over the place and quite old), cut them out, and put them in a jar. My idea is that we can pull one out when the mood strikes us and discuss.

I did a small version of this many summers ago when the kids were small. They were super keen and thought it was a really fun!
But, let’s be honest, I have a tween and teen now so times have changed.
It’s all about being strategic this time around. If I was to sit them down and show them my jar of awesomeness, I’m pretty sure I’d be met with eye rolls and complaints before they even tried out my super duper mom idea.
So here’s my plan.
I am going to place the jar strategically beside a bowl of chocolate. My kids can sniff out chocolate faster than I can, and that’s impressive. I am not going to say anything. Nothing. I am going to wait for them to notice the jar and ask about it.

Then, I am going to pretend like it’s a nothing thing that I almost didn’t even realize was there. I will respond by saying, “what, that thing?” and then I will go back to whatever I am doing.
I will not make eye contact.
I am going to act nonchalant, almost like I am disinterested in the jar that I spent hours preparing (slight exaggeration).
I will quietly observe but not initiate. I will be cautious and engage slowly and strategically.
You get the idea!
If it’s a win, they will pull out a piece of paper, not knowing what to expect, and have a bit of fun answering. If it’s not, well I gave it a good go. 🙂
100 Conversation Prompts to Use With Kids, Tweens and Teens
- The best day of my life…
- My favourite singer…
- The perfect school…
- My favourite thing about road trips…
- If I could go anywhere…
- If I could switch places with a famous person for one day…
- 10 things I would bring to a deserted island…
- If I won a million dollars…
- My favourite scary movie…
- My favourite comedy…
- Are UFOs real?
- My most embarrassing moment…
- My dream job…
- What my perfect day would be like…
- My favourite TV character…
- My favourite TV show…
- My favourite cartoon character…
- If I had 3 wishes…
- If I was one inch tall…
- If I was 30 feet tall…
- 3 rules I’d make for my kids…
- If I was invisible…
- If I could be any animal…
- If I had $100,000 to give away…
- If I was an insect…
- A recipe for the worst meal ever…
- A recipe for the best meal ever…
- If I was a Principal for a day…
- The 5 most important things in life…
- The secret to happiness is…
- It’s tough being a kid/tween/teen because…
- The most beautiful thing I’ve ever seen…
- My scariest dream…
- My best dream…
- My favourite thing to do outside…
- The best musician in the world…
- 5 things that would be in a perfect world…
- My favourite animal…
- My favourite season…
- If I could take a vacation anywhere…
- If I could star in a movie…
- If I could spend a day with anyone in history…
- My favourite sport or activity…
- If I could invent something to help people….
- My favourite summer day…
- 3 of my talents…
- I feel happy when…
- I feel sad when…
- My favourite junk food…
- My favourite thing to do on the weekends…
- My favourite song…
- My favourite book…
- My favourite colour…
- My favourite weather…
- Rain makes me feel…
- Wind makes me feel…
- Sunshine makes me feel…
- Snow makes me feel…
- Fog makes me feel…
- Today I feel…
- When I become an adult, I want to…
- What I daydream, I usually think about…
- Someday I want to…
- I can’t wait until…
- Friends are…
- Families are…
- The best thing about school is…
- The worst thing about school is…
- My favourite pizza toppings…
- I know a lot about…
- I would like to know more about…
- My favourite costume I’ve ever worn…
- Advice for a 5 year old…
- The best gift I have ever given…
- The best gift I have ever received…
- Milk chocolate or dark chocolate?
- Are you more afraid of thunder or lightning?
- Dogs or cats?
- French fries or potato chips?
- Morning person or night owl?
- Sky diving or scuba diving?
- Iced cubes or crushed ice?
- Fame or fortune?
- Fav cell phone feature… camera or texting?
- Travel the world or travel through space?
- Hot chocolate or chocolate milk?
- Travel to the past or travel to the future?
- Water slide or roller coaster?
- Make a speech or write a story?
- Frosty the Snowman or Rudolph the Red-Nosed Reindeer?
- Summer or winter?
- Chocolate or candy?
- Bike or run?
- Swim or ski?
- Sunrise or sunset?
- Ocean or mountains?
- School or summer vacation?
- Chicken wings or chicken fingers?
- Play a video game or FaceTime a friend?
- Cook a meal or bake a dessert?

If you’d like a Printable version of the conversation starters that you can cut out, subscribe to Gravel Road Living below! I’ll send a monthly email to keep you up to date on simple ideas to help busy moms create a life to love.

Hi Kim ?♀️ Wow! I’m taking some time for self care over the holidays and enthused to read all this awesome material on your site; love the wellness and self care! Thank you for sharing your gift with the universe and also the free printables! Some great journal entries for students too?
Happy holidays ?
Thank you so much Gwen! I’m so glad you are enjoying it. You are too kind. 🙂