95 Ideas to Spark a Conversation Between You and a Teenager

Thought-provoking questions to bond with the teen in your life

Co-authored by Kristen Duke and Finn Kobler

Last Updated: June 9, 2025 Fact Checked

Being the parent, guardian, or teacher of a teenager can be challenging; as they get older, it's common to feel like you're speaking different languages. Having meaningful conversations with your teen is important for their emotional well-being, though, and you should feel proud of your efforts to connect! By using conversation starters as tools for connection, you can create a safe space for sharing thoughts and feelings—all while better understanding one another in the process. We've compiled a wide variety of conversation starters for you to choose from, so you can comfortably and confidently approach your next chat with the teen in your life.

Starting a Conversation with Your Teen

Parenting expert Kristen Duke recommends asking specific questions and avoiding questions that could result in one-word answers. Instead of asking something general, like “How was your day?” show them you’re invested in their life by asking something like, “What did you learn in history today?” Get creative!

1

Fun Questions

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Get the creative juices flowing with some unique queries and scenarios. What's a hidden talent you have? If you could live at any point in history, when would you pick? Questions like these make it easy to break the ice and learn even more about the teen in your life:
- If you could travel anywhere, where would you go?
- If you could sing for any band, who would it be?
- Describe a tattoo you wish you had.
- Fiction or nonfiction?
- What’s your perfect Saturday?
- What’s your ideal birthday?
- If you could teach any subject, what would it be?
- What would you do if you won the lottery?
- Who’s the most overrated celebrity?
- What’s a superpower you wish you had?
- If you had to eat only one food forever, what would it be?
- You have 2 minutes to give me your entire life story. Go!
- Use just one word to describe yourself.

2

Questions about Favorites

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Food, colors, clothing—it's all up for grabs. It's hard to go wrong with an open-ended, "What's your favorite __?" type of question. The broader the question is, the more freedom you give your child or student to respond in their own way. Try asking questions like:
- What’s your favorite sport and why?
- What’s your favorite tweet of all time?
- Who’s your favorite grandparent?
- What’s your favorite horror movie?
- What’s your favorite sitcom?
- Who’s your favorite actor?
- What’s your favorite song?
- What’s your favorite book?
- What’s your favorite type of food?
- What's your favorite restaurant?
- What's your favorite ice cream flavor?
- What’s your favorite clothing brand?
- What’s your favorite memory?
- What’s your favorite vacation you’ve ever been on?
- What's been your favorite year of life so far?

3

Relatable Questions

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From pop culture to friend groups, the question options are endless. Differences in age and life experience present a unique challenge when you're chatting with your child or student. Thankfully, it's easy enough to bridge this gap—as long as you're asking the right questions. Stick with relatable queries that really cater to their current life and past experiences, like:
- Who’s the best rapper of this generation?
- What’s the first thing on your bucket list?
- Who’s the most annoying person in your class?
- What’s the worst thing about school?
- Who’s your best friend?
- If you could be BFFs with any celebrity, who would you pick?
- How do you get your eyeliner wings so sharp?

4

Serious Questions

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Deep, mature questions can lead to deep, mature conversations. From politics to philosophy, there's no shortage of deep, thought-provoking topics that teens can share their thoughts on. If you feel comfortable doing so, toss out a few questions like:
- If you could change anything about society, what would it be?
- Do you think it’s easier to be happy if you’re rich?
- Do you believe in capital punishment?
- Do you think it's better to be feared or loved?
- What crimes do you think should be legal?

5

Introspective Questions

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Invite the teen to take a closer look at themselves with your questions. What are you most afraid of? What would your last meal be? Offer some questions that really make them think about their identity and personal preferences, like:
- Are you an optimist or a pessimist?
- What’s your proudest moment?
- What’s one thing you would change about yourself?
- What causes you to procrastinate the most?
- Name one thing that never fails to make you laugh.
- Name one thing that never fails to make you cry.
- What’s a body part you could do without?
- What are your biggest pet peeves?

6

Spiritual Questions

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Discussing spiritual beliefs can be a fun way to break the ice. Make it clear that you're coming from a nonjudgmental point of view, and that you're honestly curious about their thoughts and opinions about spirituality. Open up with questions like:
- What do you think happens after we die?
- Do you believe in astrology?
- What tarot card do you think best represents you?
- Do you believe in karma?

7

Questions about the Past

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Everyone has silly, embarrassing, and even sad moments to reflect on. Invite the teen to go on a trip down memory lane with you, featuring questions like:
- What’s your most embarrassing moment?
- What’s your first memory?
- What’s your worst memory?
- What’s your biggest regret?
- What event do you think has impacted you the most?
- What’s the best gift you’ve ever received?

8

Questions about the Future

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From weddings to college plans, the sky's the limit. The average teen undoubtedly has a lot on their plate when it comes to the future—so why not break all those prospects down into some fun and interesting questions? Try these on for size:
- What’s your dream job?
- What’s your dream college and why?
- What does your dream wedding look like?
- If you decide to have kids, how many would you have?
- Who’s one person you hope to inspire?
- Predict one thing you think will happen in the next five years.
- If you had the option, would you want to see the future?
- What’s one thing you hope happens at school today?

9

Would You Rather Questions

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Learn more about your teen with some "Coke or Pepsi" style questions. You can learn a lot about a person with a simple "would you rather" (WYR) question; best of all, these types of questions can be a fun way to launch into a playful debate. Here are a few WYRs to get you started:
- WYR: have a food fight or water balloon fight?
- WYR: have love today or a dream house next year?
- WYR: have a pause or rewind button on your life?
- WYR: sing better or dance better?
- WYR: give up texting or the Internet forever?
- WYR: give up coffee or give up soda?
- WYR: be the smartest or the best-looking person alive?
- WYR: camp in the woods or on the beach?
- WYR: never be able to complain or never be able to lie?
- WYR: miss the first 10 minutes of a movie or the last 10?
- WYR: never be able to use the letter e or the letter a?
- WYR: never need food or never need sleep?
- WYR: be the head of a company or the head of a cult?
- WYR: wear sneakers forever or never get a haircut again?
- WYR: speak 5 languages or play 5 instruments?
- WYR: live life on 0.5 speed or 1.5 speed?
- WYR: be a dog or a cat?
- WYR: have your plane or your own car?

10

Questions about You

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Turn the tables by making them think about you for a moment. A playful self-roast can be a great way to get a conversation going—especially if you give your child or student a chance to pull the punches. Start off your convo with questions like:
- What’s one thing you would change about me?
- What’s the most embarrassing thing I do?
- What’s the ugliest thing I’ve ever worn?
- Use just one word to describe me.

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Tips

Appreciate the efforts you've made thus far in trying to connect with the teen in your life. Building a strong relationship takes time and patience—you're doing great!

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Start conversations in the car. It’s easier to talk when you don’t have to constantly look at each other.

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Use positive body language. To bond with your son or daughter, smile, nod when you agree, and avoid crossing your arms.

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