The most popular post on this blog in the last couple of years has been THIS ONE where I shared 50 funny conversation starters for teens and tweens.

I work with teens and tweens on the regular with my job as a director of one of our local homeschool co-ops. During the school year, I teach high school on Mondays and upper elementary and middle school on Thursdays. I love each day that I’m there for different reasons. High Schoolers are amazing. I’ve said it before and I will say it again… there’s no reason to fear the teen years. Teens are phenomenal humans. This particular generation of teens has much to offer in this crazy world. They are fiercely loyal, passionate fact-checkers, and bring hope to a chaotic culture. Invest in your teens and their friends. It is 110% worth it! One of my favorite parts of Mondays is lunch time. I love to sit with the students or stand or wander around. This is when they are relaxed and silly and talkative.

Thursdays this past year were insane. I had twenty 4th and 5th graders. That may not seem like much to a traditional classroom teacher… but homeschoolers just hit differently. These little people are used to being somewhat the center of attention. In most cases, this is their first classroom experience and they have to learn to share the spotlight. Their energy is amazing. This age loves to learn and loves to please. They are eager and so much fun! Lunch on Thursdays is different because I don’t sit down. I flit from the four-square court to the back of the building to the classrooms to the common areas. I monitor and make sure everyone is included and playing nice. Hormones are intense in middle school and that doesn’t always bode well in large groups… especially in competitive settings. They just need a little extra love and guidance…. and sometimes they need to be arm wrestled.

I’ve learned to keep an arsenal of random questions at hand when engaging the students. Whether it’s the younger students or the seniors, everyone loves weird questions! These are great time fillers, icebreakers, etc.

Here is my list of 50 MORE Funny Conversation Starters for Teens and Tweens.

  1. What is the best conversation topic for the middle of the night?
  2. If you were a candy bar what would you be? Why?
  3. What fantasy land do you most want to visit?
  4. Which fictional creature would you want as a sidekick?
  5. What’s the worst thing about a peanut butter and jelly sandwich?
  6. If a squirrel could talk, do you think its voice would be high or low?
  7. What is the silliest way you’ve been injured?
  8. Would you rather smell hard-boiled eggs all day or eat a fart?
  9. If your nose had to be anywhere else on your body, where would you put it?
  10. What is your go-to joke?
  11. If you could have a mythical creature for a pet, which would you choose?
  12. What is the best type of bread?
  13. What three things would you bring to a desert island?
  14. If you could start a secret society, what would it be called?
  15. If you could design a new ice cream flavor, what would it be?
  16. What would be the worst thing for the government to make illegal?
  17. Show me your go-to dance move.
  18. Do you have a secret talent?
  19. If you had a pet parrot, what would you teach it to say?
  20. If rain could be any other liquid, what would it be?
  21. Design the ultimate sandwich.
  22. What book series do you wish you could live in?
  23. If you could have a lifetime supply of anything, what would it be?
  24. What would be the hashtag of your life?
  25. What do you think will be playing on the oldies station in 30 years?
  26. Would you rather fight one horse-sized duck or 100 duck-sized horses?
  27. What’s the weirdest gift you’ve ever received?
  28. What’s your biggest irrational fear?
  29. Does round pizza or square pizza taste better?
  30. Would you rather have feet for hands or hands for feet?
  31. If you were to go on Shark Tank, what idea would you pitch?
  32. What is your least favorite scent?
  33. What’s your favorite dinosaur?
  34. Which Mario Kart character are you?
  35. Would you talk about Bruno?
  36. What is the strangest thing under your bed?
  37. If you were a shoe, would you be right or left?
  38. If you could switch places with someone for the day, who would it be?
  39. Which Olympic sport shouldn’t exist, but does?
  40. If you had to eat a crayon, what color would you choose?
  41. What’s your go-to in Rock, Paper, Scissors?
  42. If you could high-five anyone in the world, who would it be?
  43. What food describes your personality?
  44. What is your earliest memory from childhood?
  45. What song do you know every word to?
  46. Who would you be in a circus performance?
  47. If you were stuck in the woods and all the animals were friendly, which one would you hang out with?
  48. What old person tendencies do you have?
  49. What animal would be super amazing if it was the size of a horse?
  50. If your toothbrush could talk, what would it say?

**Disclaimer… many of these questions were curated from other sites.**

What would you add to the list????

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