75 Questions to Ask Your Teen (& How to Have Those Tough Conversations)

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Many teens struggle with having difficult conversations with parents. If you’re a parent of a teen, you know first-hand just how difficult it can be to talk through some of the more unsavory parts of life.

Even with the best questions for teens at your disposal, figuring out how to talk to a teenager about school, life and other topics can be really hard.

There’s so much in the world that can be unpleasant to talk about, but it’s almost always worse to leave things unsaid.

It can be hard to get them to open up at first, but if you’re ready to learn how to get a teenager to talk to you, then keep reading. I’ll provide some questions to ask teens about life to make it easier. 

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How to Talk to a Teenager (and Get Them to Talk to You)

But first, let’s explore the best ways to use these questions for teens to have real conversations. While we were all teens once, for some of us those years were long, long ago.

These days, there seems to be even more going on in the world with the influences of social media and the way teens are connecting with each other through their phones. 

Not to mention the standby “uncomfortable conversation” topics: bullying, drugs, sex, drinking, peer pressure, and general public safety. 

If the prospect of talking about any of these teenage conversation topics makes you want to run for the hills, here are some tips for effectively parenting teens while having uncomfortable discussions.

Bring up topics in the right context.

If you’re looking to chat with your teen about some recent events in the news, a case of bullying at their school, or anything else pertinent to their lives, make sure you pay attention to the setting. 

Bringing up a tough topic right as your teen gets home from school, or while you’re mid-grocery-shopping may not be the best course of action. Choose a time in a private, neutral space to broach a tough conversation.

Ask about their experiences with curiosity, not hostility.

Make sure that you give your child time and space to talk about their own experiences with the topic at hand, and that you ask respectful, open-ended questions for teens with curiosity, rather than hostility.

Remain calm throughout the entirety of your chat.

Similar to avoiding hostility, make sure you keep your tone of voice and your behavior level and warm for the whole conversation.  It doesn’t matter if you have the best conversation questions for teens. If you ask them in a tense or hostile manner, you won’t be learning the secrets of how to get a teenager to talk!

Making your child feel judged or that you are disappointed in them for anything they share with you may negatively affect their probability of talking to you about these topics in the future.

While you may learn information that concerns you or upsets you, keep those judgments to yourself while you’re having these tough conversations with your teen so they feel comfortable coming to you with their challenges.

Share your experiences, if applicable.

If you have firsthand experience from your youth that pertains to the issues you and your kid are chatting about, make sure you bring them up. 

Our kids need to hear from us that we know what it’s like to be young and to be facing the difficult parts of the world.

Thank them for their openness and honesty.

Asking hard questions for teens isn’t easy, but answering them is even harder! So at the tail end of your tough conversation, make sure you let your teen know that you’re grateful for their openness and honesty. 

If your child feels comfortable sharing their experiences, worries, and dreams with you, they will be less likely to hide their problems from you, and more likely to ask for help when they need it.

Opening the door to healthy conversations with your teen is key in making them feel supported and loved, so try out these tips next time you have an uncomfortable conversation.

If you have a teen that struggles to open up, having some fun Q&A time may help spark communication. Use the 75 questions to ask your teenager listed in the rest of this post to get the conversation started. 

75 Questions for Teens [Organized by Topic]

I’ve gathered some thought-provoking questions for teens to get the ball rolling. Of course, if they don’t feel comfortable, don’t force it, but do encourage it as much as you’re able without being too pushy. 

Questions to Ask a Teenage Guy

Learning how to talk to your teenager – especially a teenage boy – can feel daunting. This mix of serious and funny questions to ask teens can help get the conversation started.

1. What’s the most embarrassing thing you’ve ever done to get a girl’s attention?
2. What makes a good friend?
3. What are some good things about social media?
4. What are some bad things about social media?
5. What is your favorite thing about yourself?
6. What is something you would change about yourself if you could?
7. Who is someone you look up to?
8. What is the most memorable act of kindness that you have witnessed?
9. What is the cruelest thing you have witnessed?
10. What is your favorite song right now?
11. Tell me something that has made you laugh uncontrollably lately?
12. Tell me something that has made you angry lately?
13. If you could have one superpower, what would it be and why?
14. What advice would you give to younger guys about middle school?
15. What is your dream job?
16. What is one thing you don’t know how to do, but wish you did?
17. If you could be famous for one thing, what would it be?
18. Who would be the worst person to be stuck in an elevator with?
19. Who is your celebrity crush?
20. How would you describe my parenting style?

Questions to Ask a Teenage Girl

Tired of constantly wondering what’s going on in your teenage daughter’s head? These thought-provoking questions for teens could help her open up.

1. What is your favorite memory?
2. Who would you consider your best friend and why?
3. Who is your favorite teacher this year?
4. What is your favorite class?
5. What is your favorite app to use on your phone?
6. Who is your celebrity crush?
7. Do you think you would like to get married one day?
8. What is your favorite thing about my parenting style?
9. What is your least favorite thing about my parenting style?
10. If you could live anywhere in the world, where would you live?
11. What are you most afraid of?
12. What is your favorite beauty product?
13. Tell me something that makes you happy?
14. Tell me something that makes you sad??
15. Who is one person that can always make you feel better when you’re feeling down?
16. When was the last time that you laughed so hard you cried?
17. What characteristics make a good leader?
18. If there was a movie made about your life, who would you want to play the role of you?
19. What are some things on your bucket list?
20. What is something you wish you were better at?

Funny Questions for Teens

Not all teenage conversation topics have to be serious! One of the best ways to get a teenager to talk to you is to make the conversation fun! Try out these funny questions for teens the next time you want them to open up.

1. If you could be invisible for a single day, what would you do?
2. What is the funniest joke you have ever heard?
3. What is the most embarrassing thing you have ever worn?
4. If you could be a fly on the wall, who would you want to eavesdrop on?
5. If you could be in any movie, what would it be?
6. If you could choose one comedian to hang out with for a day, who would you choose?
7. What instrument do you think is the most annoying?
8. What is the most useless invention ever created?
9. What is the weirdest thing you have ever eaten?
10. Who do you think is your celebrity look alike?
11. If you had to choose one meal to eat every single day, what would it be?
12. What is one thing that your teacher could do to make your classes more fun?
13. What is something you like to do when you’re bored?
14. What secret skill or talent do you have that nobody else knows about?
15. Who is the funniest person that you know?
16. What is the best thing about being a teenager?
17. What is the worst thing about being a teenager?
18. If you could be any animal, which one would you be and why?
19. What was your favorite toy from your childhood?
20. What is the most useful thing you own?

Open-Ended Questions for Teens

By asking open ended questions, we can encourage a teenager to share what’s going on inside their heads. These questions are a great way to get to know your teenager a little bit better.

1. What would you like to learn how to do?
2. What subject is not taught in school that you think should be?
3. What television show are you currently watching?
4. How would you describe your personality?
5. When is the last time you have been excited about something?
6. When is the last time you have been disappointed?
7. What is the last thing that you and your best friend fought about?
8. What is your favorite holiday and why?
9. What do you think when you see a homeless person?
10. What is the best and worst food that your cafeteria serves?

Questions for Teens Surrounding Common Problems and Issues

Of course, teenage conversation topics can’t be all fun and games. There are times when we need to sit down and talk with our teens about serious topics or problems they may be having. Try out these questions to get those tough conversations started.

1. Do you feel pressure at school?
2. Is bullying a problem at your school?
3. What is the best way to handle a bully?
4. Do you agree with the current legal age for drinking, smoking, and voting? Why or why not. 
5. What do you think is the biggest issue that teenagers face right now?

Need Even More Questions to Ask Teens?

As a mom of college-aged kids myself, I know first-hand the challenge of figuring how to talk to a teenager who doesn’t want to talk. But with the right questions, it is possible to start hard conversations and talk more openly with your teenager on a regular basis.

If you’re in need of even more questions for teens, then check out the recommended reading list below. Each of these articles have more ideas and tips about how to talk to a teenager.

Suggestions for Further Reading:

• Can we talk? 100 questions your teen might actually answer – Having a conversation that goes beyond monosyllables can be a challenge. Here’s what teens wish you’d ask them instead. (familyzone.com)
• 50 Thought-Provoking Questions to Ask Your Teen Youth First (youthfirstinc.org)
• 100 Questions to Ask Your Teen Other Than “How Was School?” – An adolescent-assisted list of alternate conversation starters. (psychologytoday.com)
• 100 Questions To Get To Know Your Teenager – One thing that my wife and I discussed recently, was that we don’t talk to our child enough about some of the bigger issues, that we need to while we still can learn more about our teen. So, we decided to brainstorm a list of questions to ask our teen … (care.com)
• 50 of the Best (and Fun!) Questions To Start a Conversation With Your Teen Boy parent|re.mix (parentremix.com)

What do experts say about effective communication with teens?

Here are some expert opinions on effective communication with teenagers: 

1. Dr. Sarah Thompson, Child Psychologist: “Having difficult conversations with teenagers is a crucial aspect of parenting during the teenage years. It’s important for parents to choose the right time and place for these discussions, avoiding confrontations at the dinner table or in the midst of other family activities. Research findings consistently show that open-ended questions and active listening are powerful tools in navigating tough topics. This creates an open dialogue, providing a safe space for teenagers to express themselves and fostering a positive change in the parent-teen relationship.”
2. Counselor Emily Rodriguez on Social Media and Tough Conversations: “In today’s world, social media adds a layer of complexity to the already challenging task of communicating with young people. Parents of teens must initiate frequent conversations about social media usage, peer pressure, and the potential impact on mental health. A supportive tone of voice, coupled with open-ended questions, can turn what might seem like a tricky conversation into a two-way dialogue. By incorporating the importance of a request over a rule, parents can guide teenagers towards making good choices in their online interactions.”
3. Parenting Expert, Dr. Alex Bennett, on the Power of Regular Family Time: “Establishing regular family time is a great way to create a safe space for deeper conversations. The dinner table can serve as an ideal setting to start meaningful conversations, as the soft tones of voice and the supportive atmosphere can make even the most challenging topics more approachable. Spending time together, away from electronic devices, promotes open communication and strengthens the parent-teen bond. It’s not about having a power struggle but creating an environment where teenagers feel heard and understood.”
4. Laura Martinez, Family Counselor, on Peer Pressure and Teenage Protests: “Navigating peer pressure and teenage protests requires a delicate balance. Parents need to approach these sensitive issues with sensitivity and understanding. By acknowledging teenagers’ needs and experiences, parents can engage in honest communication that goes beyond parental messages. A positive tone of voice, coupled with age-appropriate language, can transform a tricky conversation into an opportunity for deeper understanding. Remember, a little bit of flexibility goes a long way in building a healthy relationship.”
5. Dr. Jonathan Turner, Adolescent Psychologist, on Deeper Conversations: “The teenage years are a crucial time for young adults to explore their own identities. Parents can support this journey by encouraging deeper conversations about their child’s actions, experiences, and values. Engaging in frequent, two-way conversations not only helps parents understand their teenager’s perspective but also creates an atmosphere where difficult questions are welcomed. This approach, combined with the acknowledgment of the importance of a request rather than imposing parental rules, fosters a better relationship between parents and teens.”
6. Karen Wong, Parenting Educator, on the Importance of Active Listening: “Active listening is the key to unlocking the doors to a teenager’s world. Parents should strive to understand the emotions and thoughts behind their child’s words. Research findings emphasize the significance of regular, non-judgmental conversations. By acknowledging the challenges teenagers face in a fast-paced world, parents can respond in an age-appropriate way. Creating an open dialogue that respects teenagers’ perspectives can lead to healthier relationships and positive emotions for both parents and their teens.”

Do you have a tip for having tough conversations with teens? Or maybe some fun questions to ask them about life? Drop it in the comments! I’d love to hear from you!