Embarking on a mentoring journey is a powerful commitment to positively impacting a young person’s life. Breaking the ice and initiating meaningful conversations can be a challenge. This post will give tips to help you start conversations thoughtfully, ensuring your Little feels valued and heard.

Let’s start with some obvious things to keep in mind. It’s important to carve out moments of genuine connection. When meeting with your Little, turn off your phone and resist the temptation to glance at your screen. Showing that they have your undivided attention fosters trust and sets the stage for open and authentic dialogue.

Thoughtful conversations don’t have to be forced or contrived. Creative and enjoyable ice-breakers can spark them. Remember, the goal is to make every interaction meaningful and satisfying.

Conversation starters for teens and with young adults

Teens are more mature than many adults give them credit for, so thought-provoking questions can do a lot to engage with your Little and get them into a meaningful conversation. As a mentor, ask questions that are specific, exploratory or conceptual. Generic questions like “How’s school?” will get you generic answers. Good questions for teens like, “What’s something you learned that surprised you recently?” might get you an interesting conversation. 

• Explore passions
• Future aspirations
• Reflect on growth
• Pop culture and trends
• Friendships and relationships
• Personal values
• Hypotheticals
• School life
• Creativity and expressions
• Self-care and wellbeing

These are good starting points, reword and contextualize these questions for your Little in a way that would resonate with them most. 

Questions for teenagers that encourage exploring passions

This is a great place to start. Ask them about what they are passionate about.

• What skill or hobby have you always wanted to master?
• What would it look like if you could create the next big video game or app?
• What activities or hobbies inspire you?
• If you could spend a day immersed in any form of art, what would it be?

Questions to ask teenagers about aspirations

Try to dig in and find out if they have an idea of what they want to do in life.

• Where do you see yourself in five years, personally and professionally?
• If you could do one thing all day and get paid for it, what would it be?
• What goals or dreams do you have for yourself in the next few years?
• If you could choose any profession, what would it be?

Questions to ask a teenager about life 

Talking to a teen about life reflections could be met with a bit of hesitation in the beginning. If so, revisit them later once trust has been established.

• What’s a challenge you’ve faced, and how did you overcome it?
• In what ways do you feel you’ve grown or changed in the past year?

Easy conversation starters for teens! Pop culture and trends

If your teenage Little is reluctant to talk about themselves, they may be more open to talk about what interests them, like music, books, movies, games and other things in popular culture. These are always fun topics to discuss.

• Do you have any celebrity role models? What qualities do you admire in them?
• What’s your take on the current state of music, movies, or social media trends?
• Do you have a favorite movie or music genre?
• If you had the chance to meet any fictional character, who would it be and why?
• How do you think social media shapes the perception of adulthood and success these days?

Teenage conversation starters about friendships and relationships

• What qualities do you value most in your closest friends?
• How do you face challenges in your friendships or relationships?

Thought-provoking questions about teens’ personal values

• What social or environmental issues do you feel passionate about, and why?
• What causes or issues do you feel strongly about, and why?
• If you could make a positive change in the world, what would it be?
• What is a character trait of yours that you value?

Hypothetical questions for youth

• If you could take a spontaneous road trip, where would you go, and who would you bring?
• What’s the most daring thing you’ve ever dreamed of doing?
• If you could possess any superpower for a day, what would it be, and how would you use it?
• If you could step into the shoes of any fictional character for a day, who would it be and why?
• Imagine you can time travel. What era or moment in history would you visit?

Conversation starters about high school life

• What subject at school do you find most interesting, and why?
• Is there anything about the education system you would change?
• What’s something you learned that surprised you?
• Which teacher do you like best or worst, and why?

Talking about their creativity and expression

• How do you use creativity as an outlet for your ideas?
• If you could create a piece of art that represents who you are, what would it look like?

Questions to ask about self-care and well-being

• What activities help you relax and take care of your mental health?
• How do you prioritize self-care in daily life?

Conversation starters for tweens and middle schoolers

On the cusp of high school, tweens and middle schoolers are learning more about the world every day and are brimming with thoughts about it. These questions will help you unlock those thoughts and engage with your tween Little.

Explore middle schoolers’ interests

• What’s something you’re into these days, like a hobby or activity?
• If you could have any superpower, what would it be and why?

Ask them about future fun

• If you could plan the ultimate weekend with friends, what would it include?
• What’s one thing you’re excited to learn or try in the upcoming school year?
• Any books or stories you’ve read recently that you absolutely loved?

Questions to ask tweens about their friendships

• How do you make new friends, especially when starting a new school year?
• What qualities do you think make someone a good friend?

Conversation starters for elementary students

Home, school, friends, sleep – it may not sound like a lot, but there are so many engaging questions to ask and the answers will almost always surprise you.

Easy questions about kids’ favorite things

• What’s your favorite thing to do during recess?
• If you could have any animal as a pet, what would it be?

Questions about playtime and fun

• What games do you love to play with friends?
• If you could create a new game, what would the rules be?

Bookworm talk for grade-schoolers

• Any favorite stories or characters from the books you’ve been reading?
• If you could step into the pages of a book, which one would it be?

Ask them about dreamy wishes

• If you had three wishes, what would you wish for?
• What’s your dream job when you grow up, and why?

Kindergarten conversation starters

Conversation starters for 5-year-olds in kindergarten can help them, as they are just starting to learn how to express themselves and how to think about the world. 

Fun discussion questions about animal adventures

• If you could be any animal for a day, which one would you choose?
• What’s your favorite animal sound?

Ask them to describe superhero dreams

• If you could have a superpower, what would it be?
• What would your superhero name be?

Questions about favorite playtime activity

• What’s your favorite game to play?
• If you could make up a new game, what would it be about?

Favorite snack?

• What’s your go-to snack when you’re feeling hungry?
• If you had a magic snack, what would it be?

Favorite stories?

• Do you have a favorite bedtime story?
• If you could make up your own story, what would it be about?

Journal your conversations

Some Bigs start shared journals when they are matched. It can be fun (and funny) to revisit kids’ answers as they age, and their families will treasure the recorded memories! Consider doing a mentor-mentee journal and every so often, when you get together, have a journal day where you ask each other questions and journal your answers!  

Keep in mind these are just suggestions. Make each question your own, and make them sound genuine and caring.