65 Super Fun This or That Questions for Teens 

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Teenagers are known for their boundless energy, unique perspectives, and liking for expressing themselves. Yet, when it comes to striking up conversations with them, it can sometimes feel like navigating a maze. Finding the right words to connect with teens can be challenging, but the solution might be simpler than you think. Let’s talk about some this or that questions for teens that will get them talking!

These versatile queries provide an excellent way to engage in fun, insightful, and meaningful conversations with the young adults in your life. These questions can be an essential tool for parents, educators, mentors, and anyone else eager to bridge the communication gap with teens.

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What Are This or That Questions?

“This or That” questions are a form of inquiry in which individuals are presented with two options and asked to choose between them. These options are typically presented in a way that requires the individual to select one over the other, expressing their preference. These questions are often used as a fun and engaging way to spark conversation, gain insights into someone’s personality or preferences, or simply to make choices in a playful manner.

For example, a “This or That” question might ask someone to choose between “Chocolate or Vanilla?” In this case, the person is expected to select either chocolate or vanilla as their preferred flavor.

The questions can range from simple and lighthearted and silly questions like food preferences to more thought-provoking or interesting questions that reveal deeper insights into a person’s values, interests, or priorities.

“This or That” questions are commonly used as conversation starters, icebreakers, or as a fun game among friends, family, or even in educational settings to engage and interact with others in an entertaining and often revealing way.

Most of all, asking these types of questions is a fun activity and a great way to spark conversation with teenagers. 

Why Do “This or That” Questions Matter?

If you’ve been around many teenagers, you’ll know how difficult it can sometimes be to get them to communicate. This or that questions are a fun way to spark up a conversation with teens and possibly even get them to think critically. Here are some reasons this or that questions matter: 

1. Engagement: “This or That” questions are an interactive and engaging way to draw teens into conversation. They invite participation and encourage young minds to express their preferences.

2. Versatility: These questions cover a vast spectrum of topics, ranging from light-hearted and entertaining to profound and thought-provoking. You can tailor the questions to the interests and personalities of individual teenagers.

3. Nonjudgmental: “This or That” questions have no right or wrong answers. They create a judgment-free space where teens can freely express their opinions, fostering trust and openness.

4. Personal Insight: Asking these questions provides valuable insights into a teen’s likes, dislikes, values, and aspirations, helping you understand them on a deeper level.

5. Critical Thinking: Many “This or That” questions encourage teens to think critically and provide reasoning behind their choices. This can lead to rich discussions and the opportunity for teens to articulate their thoughts.

What are some This or That Questions for Teens?

Here are some good questions to ask teens. These fun questions are a fantastic way to get teens talking:

46. Mobile gaming or Console gaming?

47. Camping or Glamping?

48. Disneyland or Universal Studios?

49. Basketball or Football?

50. Peace and quiet or Social gatherings?

51. Ice cream or cake?

52. Famous athlete or favorite singer?

​53. Theme park or state park?

​54. Cell phone or laptop?

55. Small group of close friends or large group of people?

What are Some Other “Would You Rather” Type Questions for Teens?

56. Would you rather be stuck in a romantic comedy with your worst enemy or in a horror movie with your best friend?

57. Would you rather be rich for the rest of your life or have guaranteed great health for the rest of your life?

58. What favorite food would you eat every single day if you could?

59. If you could spend a day with a famous musician, who would you pick?

60. What famous movie star would you rather have dinner with?

61. If you had to pick only one junk food to eat for a month, what would it be?

62. If you had to pick one favorite song to listen to on the radio, what would it be?

63. Would you rather meet a famous actor or go on your dream vacation?

64. Would you rather make a lot of money at a job you hate or work the job you love and make less money?

65. Do you think it’s harder to be a teen or an adult?

These questions can serve as conversation starters, icebreakers, or even be incorporated into games and activities. Whether you’re a parent trying to connect with your teenager, a teacher fostering meaningful dialogues with your students, or simply someone seeking to engage with the teens around you, “This or That” questions can be your secret weapon.

What are Some Other Discussion Questions for Teens?

Here are some other topics and conversation-starter ideas that are appropriate for teens:

Being a Good Friend: As a parent, being a good friend to your child involves listening without judgment, offering support, and sharing their joys and concerns.

The Only Child Dilemma: If your child is an only child, create opportunities for socialization and encourage them to build friendships outside the family.

The School Bus Chronicles: Ask high school students about their daily experiences on the school bus to understand their interactions and concerns.

Favorite Book Discussions: Engage your child in discussions about their favorite book, and share your own favorites to encourage a love for reading.

Whole Life Learning: Encourage learning throughout your child’s whole life, not just during school years. Ask about their interests and what they’d like to explore.

Photographic Memory Fun: Ask if they know anyone with a photographic memory and how it could be an advantage in school or daily life.

Making New Friends: Discuss making new friends and how to identify genuine connections among a little bit of skepticism.

Walking on Hot Coals: Discuss moments when they’ve faced their fears, like walking on metaphorical “hot coals,” and what they’ve learned.

Imaginary Pet Dragon: Explore their imagination by asking about their ideal pet dragon and its adventures.

The Quest to Be the Smartest Person: Discuss the importance of continuous learning and that nobody can be the smartest person in everything.

Celebrity Crush Confessions: Talk about celebrity crushes and share your own teenage celebrity crush stories.

Handling Defeat on the Losing Team: Discuss how to handle defeat gracefully when you’re on the losing team.

The Next Time Around: Encourage optimism and talk about learning from past experiences and doing better next time.

Finding the Right Place: Help your child explore their interests and passions to find the right place for their talents.

Dream College Desires: Talk about their dream college and what they need to achieve to make it a reality.

Navigating the Teen Years: Share your experiences during your own teen years and discuss the challenges they may face.

TV Show Favorites: Discuss favorite TV shows and use them as a basis for conversations on various topics.

Cherished Favorite Places: Talk about your favorite places and the memories associated with them.

Dealing with the Worst Player: Discuss the importance of teamwork and supporting the “worst player” on a team.

Maximizing Free Time: Help your child find productive and enjoyable ways to spend their free time.

Asking Funny Questions: Lighten the mood with funny questions to keep the conversation light and enjoyable.

Fantasy Shopping Spree: Ask about their dream shopping spree and how they’d spend unlimited money.

School Cafeteria Chronicles: Inquire about their experiences in the school cafeteria and the friends they’ve made there.

What is a Good Setting for Conversations with Teens?

The setting for “This or That” questions with teens can vary depending on the context and your relationship with the teens. Here are some suitable settings and scenarios for using “This or That” questions effectively:

Family Dinners: Incorporate “This or That” questions into your family mealtime routine. It can be a fun and interactive way to engage with your teenagers while enjoying a meal together.

Road Trips: Long car rides are an excellent time to ask “This or That” questions. It can help pass the time, reduce boredom, and spark interesting discussions.

Game Nights: If you’re having a game night with family or friends, consider including “This or That” questions as part of the games you play. It can be a great addition to board games or card games.

Campfires: Whether you’re camping in the wilderness or just enjoying a backyard bonfire, “This or That” questions can make the evening more entertaining and memorable.

Teen Party: If you’re hosting a party for middle school students or teenagers, especially for birthdays or special occasions, use “This or That” questions as an icebreaker or a party game.

Classroom or Educational Settings: Teachers can use these questions to engage students and promote discussion during class. It can be incorporated into lessons as a fun and educational activity.

Mentoring or Counseling Sessions: If you’re a mentor or counselor, these questions can be a useful tool to get to know the teenagers you’re working with and establish rapport.

One-on-One Conversations: During one-on-one talks with a teenager, you can use “This or That” questions to create a more relaxed and open atmosphere. This is especially useful for parents, guardians, or mentors.

Online or Virtual Chats: In today’s digital age, you can use “This or That” questions in virtual settings like a video call or a text message. It’s a great way to stay connected and engage with teenagers who may not be physically present.

Special Occasions: “This or That” questions can be integrated into special occasions like family gatherings, holidays, or celebrations, encouraging interaction among all family members, including teens.

Sports Practices or Activities: If you’re a coach or organizer of a sports team or extracurricular activity, use these questions as a fun and bonding activity during breaks.

College or University Orientation: For educators or mentors working with older teens who are transitioning to college or university, “This or That” questions can be part of orientation or team-building activities.

Social Club Meetings: If you’re part of a social club or youth group, you can include “This or That” questions as a regular feature in your meetings to encourage interaction and camaraderie.

Remember that the setting should be comfortable and conducive to open conversation. It’s essential to adapt the questions to the context, and it’s equally important to respect the preferences and boundaries of the teenagers involved. Using “This or That” questions in appropriate settings can help facilitate engaging and enjoyable interactions with teens while promoting communication and understanding.