Surprising Teen Conversation Starters

We only have a few summers left when our kids are tweens and teens. We want to make the most of them. We want to have heart-to-heart conversations with deeper connection, more meaning and certainly more fun. But often and rightfully so, our teens have their own agendas and they certainly have their own pressures to navigate the gulf between family and school, hormones and dates, digital life and ordinary reality. They occupy a different social location than adults, which means they have a unique personal and cultural perspective.

Communicating consciously to build a happier, more meaningful and more satisfying relationship with our tweens, teens, and young adults means we must listen as non-judgementally as possible. Knowing how to communicate our thoughts and feelings may not come naturally, which is why it helps to have some communication models. Many of us did not grow up with healthy communication role models. We may have grown up with authoritarian ways of parenting and communicating that simply will not prepare this generation for the future.

[perfectpullquote align=”full” bordertop=”false” cite=”” link=”” color=”” class=”” size=””]Dr. Shefali Tsabary, Oprah’s parenting expert says, “This generation will not tolerate anything short of co-creation.”[/perfectpullquote]

Co-creation communication is simply a mindset and skill set that engages teens and parents to be fully responsible for building relationships. Consciously practicing co-creation communication skills may help us enjoy our teens more and develop the deep meaningful bonds we long for. Communicating this way also gives tweens, teens and young adults a model for how they can communicate in college and the world of work.

To open this high level of communication, open-ended questions may be helpful. Sociologists and journalists use open-ended questions as an interview technique. When asked lovingly and non-judgementally, tweens, teens and young adults tend to open up. This skill may help you get to know your teen in a different way. The following are a few open-ended questions you can use to start conversations. Remember the purpose of this exercise is simply to  listen and learn.

Open Ended Question Examples

Open-ended questions are phrased in a way to require more than a yes or no answer. Each question is about a specific area of teen life and has a sample follow up question. As you practice open-ended questions conversation starters, you will come up with your own natural follow-up questions.

Social Life

1.)Who do you consider to be your best friend right now?

a.) What do you like best about ______ (name the best friend)?

 b.) Do you hang out with ________ at lunch?


2.) Tell me about your favorite class today?  Or,

3.) Tell me about your least favorite class?

Tip: This is not a conversation about homework or grades. Teens are more likely to respond to coaching about homework if they believe you are interested in how they feel about school.

Leisure Time or Hobbies

4.) What do you like to do on weekends when you have alone time?

a.) Is there something you would like to do with your friends that you don’t have time or money to do?

5.) Who is your favorite artist, singer or band right now?

a.) What do you like about them? This may lead to an invitation to listen to music.

Tip:  Don’t bypass this opportunity.


6.) What would you like to do with the family this weekend?

a.) What bugs you the most about your little sister?


Tip: Be prepared for the answer without jumping into advice giving. This is the perfect opportunity to compliment your teen’s sibling relationship. You may want to say something like this, “Thank you for not yelling the other day when Ashley went into your room without permission.”

Personal Development, Health or Spirituality

7.) I have been trying to meditate, how do you best recharge your batteries after a stressful day at school these days?

8.) I have been working on eating more vegetables, do you have a health goal to share?


If it feels awkward, try again. Then next time you are alone together, try again. Relationship building is hard work, and it takes practice over time.

Tip: Ask these questions casually. Teens might feel put on the spot if they feel interrogated or think they will get in trouble for their answers. One mom shared she has these conversations in the car when traveling to school or after-school activity. When teens are not required to have eye contact, they don’t feel interrogated or threatened by open-ended questions.


Laura Lyles Reagan

Laura Lyles Reagan

Author and Communication Expert

Laura Lyles Reagan is a family sociologist, parenting coach and author of How to Raise Respectful Parents. She enjoys conversing with her two daughters every day. For more information, visit,  

Join us on Sunday, June 23rd at 9PM EST/6PM PST for a special webinar with Laura! Alexa and Nancy will chat with Laura about making teen and tween communication easier and more productive!  Register for this FREE webinar below.

If you can’t make it live, we’ll send you the replay. Just make sure you’re registered, so we can send it to you.

All webinar attendees will have an opportunity to win a copy of Laura’s book, How to Raise Respectful Parents, or a copy of Lose The Cape 3:  Ain’t Nothing But a Teen Thang! 

How To Talk So Your Teen Listens!