101 Conversation Starters for Teens to Connect, Laugh and Get into Their Head

Because one-word answers don't tell you much about what your teen is thinking, feeling or dreaming about...

by Nancy Reynolds

This post: 101 Conversation Starters for Teens to Connect, Laugh and Get into Their Head

Ahhh… one-word answers. Teenagers are notorious for responding in as few words as humanly possible. (Lucky for you if your teen is one of the few chatty ones!)





And, the dreaded, “k.”

It’s like pulling teeth to get them to open up to you, express their feelings, share what’s happening in their world, and talk to you when life is hard.

As parents, we want to be part of their world, but our kids are pretty darn good at being tight-lipped. That’s why we have to be “slightly” sneaky by asking targeted, open-ended questions to get the conversation rolling. 

Before you dive into these conversation starters for teens, remember these tips:

  • It’s totally normal for kids to “cocoon” and become less talkative when they become teenagers. Don’t take it personally.
  • Don’t push it if your teen isn’t in the mood to talk. With teens, timing really is everything.
  • Listen a whole lot more than you talk. This is your teen’s time to open their heart… give them the floor.
  • Hold your judgment and criticism. If you want your teen to open up, they have to feel it’s safe to do so.
  • Be available. Teens have a tendency to get chatty late at night, in the car, and when there isn’t much direct eye contact. Seize the opportunity when it presents itself. This time it’s on their terms and that’s what makes it special.
  • If your teen drops a bomb and tells you something you disapprove of, your first response should always be, “I’m really happy you felt comfortable telling me.” Don’t dive into an immediate lecture or yell. Your teen will shut down.
  • Show true curiosity in their thoughts, views, perspectives, and feelings. They really do have a lot to say if you let them.
  • Have fun with your teen. Stop being so darn serious. And, take your mom (or dad) hat off for a while… it’ll do your relationship with them so much good!
  • This is your chance to dive into what’s really happening in their lives – their hopes, views, fears, worries, friends, dreams, and mental health. Listen. Validate. Show compassion. 

101 Conversation Starters for Teens to Connect, Laugh and Get into Their Head


Stumped on what to say to get the conversation rolling with your teen when you’re in the car, making a snack together, out for lunch, or hanging out in their bedroom at night? These 101 conversation starters for teens will help your teen open up to you so you can connect more, laugh and get into their head.

Questions About Their Happiness, Self-Esteem & Life Challenges 

1. If you could do anything today that would make you happy, what would it be?

2. What is the one thing that stresses you out the most?

3. If you could make one positive change in your life, what would it be?

4. If you could change one thing about yourself what would you change?

5. What do you see when you look in the mirror?

6. What scares you the most about your future?

7. What’s something you really love about yourself?

8. What’s something that makes you feel really good about yourself?

9. When you’re stressed out, what makes you feel better?

10. What is the hardest thing about being a teenager?

11. Do you ever feel lonely? What makes you feel less lonely?

12. What is your biggest challenge in life right now and how can I help take the pressure off?

13. What makes you feel insecure about yourself? (All teens are insecure – some more than others. Here’s your chance to find out what rattles your teen’s confidence so you can boost them up!)

14. What makes you feel anxious or depressed? What do you do when that happens? 

15. Are you happy with your body? What would you change about it?

Questions About Your Relationship with Your Teen

16. If you had to choose ONE thing that I could give you, would you rather have hugs, favors, gifts, or my undivided attention? (Find out what your teen’s love language is.)

17. What is the one thing I (mom or dad) can do to make your life easier?

18. Do you wish you had more freedom in your life? How so?

19. If I took one rule away, which one would it be and why?

20. Someday, when I’m gone, what’s the one thing you’ll always remember about me?

21. What is the one thing I (mom or dad) do that bugs you the most? (No fair getting upset about their answer… take their answer and learn from it. Questions like this can really strengthen your relationship because it spawns open/honest communication.)

22. If I told you that you didn’t have to do one chore anymore, which one would you choose?

23. Do I embarrass you? How? 

24. What do you wish we talked about more? (This is your chance to find out how to really connect on a deeper level with your teen.)

25. Is there something you wish you could tell me, but you’re afraid to because you think I’ll be upset? (Make sure your teen knows they don’t have to tell you what it is… it’s more important to find out IF they’re keeping things from you and let them know they can come to you about anything.)

26. Do you wish we could spend more time together or are you happy with the way things are? 

27. Do you think I nag you? Why?

28. What is the one thing I could do differently as a parent that would help us get along better? (Another great question. Don’t get upset by their answer. Just take it in stride and learn from it.)

29. If we played hooky, what would you want to do together?

30. What do you love most about your home life? What do you like the least? (This a powerful question that will give you insight into how your teen feels about being home... and, how you can make it better so they look forward to coming home.)

31. What’s the one thing I do for you that you love?

32. Do you feel my rules are too strict? Why?

Questions About Friendships & Dating

33. What are the most important qualities you look for in a friend?

34. Would you consider yourself a good friend? Why?

35. Do your friends have good relationships with their parents?

36. Which of your friend’s parents do you respect the most and why?

37. Which of your friends do you admire the most and why?

38. If you could have one friend who really knows you, cares about you, and supports you or 20 popular friends you weren’t really that close to, which would you choose? 

39. When you’re with your friends and they’re doing something you don’t want to do, how do you handle it?

40. Are you jealous of any of your friends? Why? (Another great question that reveals your teen’s insecurities. Once you know what they’re insecure about you can dive in and boost them up.)

41. If your best friend had to describe you in three words, what do you think they’d say?

42. What’s the one thing you do that none of your friends do?

43. What qualities do you look for in a boyfriend/girlfriend?

44. How important is it to you to have a boyfriend or girlfriend?

Questions About School, Homework & Time Management

45. Which teacher has had the most positive influence on you? Why?

46. If you had the chance to tell your school principal one thing, what would you tell them?

47. Do you feel you have too much to handle in life right now?

48. What’s your most difficult subject in school and why?

49. Do you think the education system puts too much pressure on kids today and why?

50. What could I do to make doing your homework easier? (Ahem… besides actually doing it for you.)

51. What distracts you the most when you’re doing homework or studying? (A great conversation to toss out tips on how to get and stay more focused and organized.)

Questions that are Thought-Provoking

52. If you could travel anywhere in the world, where would you go?

53. What’s your opinion on gun control, global warming, homelessness, the way our country runs the government (or other topics that might get them thinking)? (Politics and world news are great conversation starters with teens – they’re far more worldly than we realize.)

54. If you volunteered to support one cause, what would it be and why?

55. What’s your favorite thing to do in your spare time and why?

56. What’s your favorite kind of music? What’s your favorite song?  Who’s your favorite band? (Then, listen to it with your teen.)

57. What bugs you the most about your sister/brother? What do you love about them? (This question can help you better understand sibling relationship dynamics so you can work on fostering the bond.)

58. What’s something you want to be remembered for?

59. What’s your favorite season and why?

60. Describe your idea of a perfect day.

61. What’s the one thing you hope you will accomplish in your life?

62. What’s one accomplishment in your life that you’re most proud of?

63. What’s the best thing that’s ever happened to you?

64. What’s the worst thing that’s ever happened to you?

65. Do you think having morals are important in life? Why? (Morals… the foundation of good decision-making.  Find out how much emphasis your teen places on having a strong moral character and then use that knowledge to foster it.)

66. Where do you see yourself in the next year, in 5 years, or 10 years?

67. Do you want kids someday? How many?

68. Would you rather be the smartest, the sweetest, or the most popular kid in your school? Why? (An interesting question because it helps you understand if popularity is important to your teen and what matters to them.)

69. If money was no object, what would you buy today?

70.  Do you think technology is hurting or helping your generation? Why? (A great question to use as a springboard to talk more about cellphone usage and how social media is impacting teens and their mental health, etc.)

Questions that are Lighthearted and Fun

71. Which celebrity inspires you the most and why? (Is it someone pretty or handsome, someone wealthy, someone known for their kindness and philanthropy, someone with power? This is actually a powerful question.)

72. If you won a million dollars in the lottery today, what would you do with the money?

73. If you could have one super-hero quality, what would it be?

74. If you could be incredibly talented at one sport, which sport would it be and why?

75. If you had to be one animal, which one would you choose and why?

76. If the house was burning down, what is the one thing you’d grab before you rushed out the door? (Is it their cell phone? Their laptop? The dog? The cat? Their journal? What really matters to your teen?)

77. What’s your idea of the absolute perfect vacation? (If possible, plan it!) 

78. What’s your favorite movie and why? (Then, watch it with your teen.)

79. What’s your favorite television show and why? (Say, “Next time you watch it, let me know. I’d love to watch it with you.”)

80. What’s the weirdest thing you’ve ever done?

81. If you had to eat only chicken nuggets or pizza for an entire month, which one would you choose?

82. If you could drive any car, which one would you drive?

83. If someone gave you $10k to give up social media for a year, could you do it?

84. What type of TikTok videos do you like to watch? (Then… watch a few videos with them.)

85. What’s your favorite app on your phone? (Hmmm… you could learn a lot from this question.)

86. What’s your idea of the perfect date?

87. What makes you laugh?

88. If you could make one dream come true, what would it be?

89. Who’s your favorite relative and why? 

90. If you could take one movie star/celebrity on a date, who would it be and why?

91. What’s your favorite movie quote?

92. What’s your favorite book and why? (Then, read it, too.)

93. What’s something you want to learn this year?

94. What’s your favorite holiday and why? 

95. If you had to choose between living in the mountains or living on the beach, which would you choose?

96. If you could trade places with one person, who would it be? Why?

97. If you could bring one person back to life, who would it be? Why?

98. What regret do you not want to have in life?

99. What is your biggest pet peeve?

100. What’s your dream job? Why? 

101 What’s something you’re looking forward to right now?

If you enjoyed reading, “101 Conversation Starters for Teens to Connect, Laugh and Get into Their Head,” check out these posts!

Just Between Us: 10 Parent & Teen Journals to Keep Your Teen Talking

How to Talk to a Teenager Who Doesn’t Want to Talk

6 Ways to Connect with Your Teen: Step into Their World

What are your favorite conversation starters for teens? Share your thoughts in the comments section below!

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