20 Ways to Start Conversations with Teens and Tweens

Hello Families!

Hope you’ve had a terrific end to your week and your having a wonderful weekend! For the last few days, I’ve been presenting at the United States Gymnastics Congress and Olympic Trials in Philadelphia, with scores of athletes, coaches, gymnastics school owners, judges, and children everywhere I turn! As you can imagine, the energy here is very high…perhaps you’ve been watching it on TV?

During this brief absence, my young colleague, Vanessa Van Petten, is here to do a great guest post from her sharp youth perspective. Being so young herself, she wants to tell you what’s really going on and how you can really help your teens and tweens! See you Monday!

20 Ways to Start Conversations with Teens and Tweens

How was your day?


How was school?


How was your test?


Anything you want to tell me?


Now that its summer, a lot of parents and the families I work with are focusing on communication skills because we are finally done with school for a bit. The biggest problem is how to get us young people talking and engaged.

I find that some of the best ways to do this is to play games like Scrabble, Clue or Sorry that you can all engage over the common game. Or, as I recently discovered games that are all about talking. A friend recommended one called Kubit2Me, which, of course, anything that has to do with Teens I ordered immediately to play with my clients and my teen girl groups and it is fabulous! I got one for my sisters to play at their birthday party–a very good Truth or Dare section and have been using them with the families I coach. So, this post is inspired by the questions and responses I got from Kubit2Me group, thanks!

-Ask over dinner

-Ask over dessert

-Leave a few cards with questions in the car for long drives

-host a sleepover for your son/daughter and their friends and encourage them to play. (I think its great when teens can also play these kinds of games with each other because it deepens friendships and bonds–hard to come by in the social networking world!)

-Play at a family reunion

-Ask your adult friends (I do this with mine all the time–in between Wii games of course)

I came up with some and borrowed some from the cards–a few are a little mature, but I find those table topics get the best conversation going!

1. If you had to give every human being one quality, what would it be and why?

2. Do you have any recurring dreams? Describe them?

3. What is the meanest thing someone could say to you?

4. If you could be a famous athlete, actor, writer or musician which would you choose and why? (It is fun to guess what the other people in the group will say before divulging answers)!

5. If you were invisible where would you go and what would you do?

6. If your life was made into a movie, who would play you? why?

7. If you could invent one thing what would it be?

8. What is the greatest song ever written?

9. Do you believe in heaven? What does yours look like? Is it different for everyone?

10. What is the most important quality for a boss to have?

11. If you could know one thing about the future, what would it be?

12. DARE: Eat your favorite food, before you swallow spit it out and re-eat it (teens love playing the truth or Dare Kubit2Me and I don’t think I laughed so hard in a long time, this was my favorite one–and the grossest)

13. How do you choose your friends?

14. What is the first thing you notice about a person?

15. What do you think is the biggest problem in the United States and Why?

16. Describe the most beautiful thing you have ever seen.

17. What would the cover of your autobiography look like if it could not be a picture of you or your family?

18. If you could trade places with anyone in the world who would it be and why? How about someone in your family?

19. Do you ever talk to yourself? When and what do you say?

20. Tell the group (or other person) the most attractive thing about the person on your right.

I really love to engage youth in intelligent conversations about values, ideals and goals. A lot of these questions are a sneaky way to get these ideas out in the open and I often play these games with the kids I work with to really get to know them. I hope you take sometime to play them with your kids, who knows you might learn something new about them!?

Add your conversation starters in the comments!

Vanessa Van Petten is the teen author of the book “You’re Grounded!”—a parenting book from a young perspective. She keeps an active blog for parents who want to know what their kids are really doing online, at High School parties or when parents are looking the other way. Her candid and young perspective, as well her constant survey of resources and updates about this generation of young people are a treasure trove for parents.