100 Conversation Starters for Teens: A Therapist’s List for Parents and Counselors

By the licensed therapists at Santos Counseling

Let me start by sharing that this is Dr. Santos of Santos Counseling writing this blog post. I remember my first year as a counselor working out of the Winston-Salem, NC office with kids and teens. I remember the challenge that came with speaking to teens. I find that talking to a teenager is not a skill anyone is born with.

Most parents, including me, figure it out through years of trial and error. I have to say that mostly error, if we’re being honest. And most therapists working with teens have a mental Rolodex of questions that actually get somewhere, because “how was school” gets nowhere.

This is that Rolodex, written down. Below are 100 conversation starters organized by mood, topic, and intent. You will find that some are for casual daily use, some for deeper moments, some specifically designed for therapists and counselors working with adolescents.

My hope is that you are able to pull from the list what’s useful. Skip what’s not. To be honest with you, a good question for one teenager is a bad question for another, and the same question can land differently on a Tuesday than on a Sunday. If you are ready to start counseling for your teen, please complete the form on this page.

How to Actually Start a Conversation With a Teenager

Did you know that effective counseling includes ground rules? I often do this with my clients. We talk about what needs to happen to create success and healthy change.

A few ground rules that make the questions below work:

• Ask questions in the car. No eye contact + a captive audience + a defined end point (the drive) equals the best teenager-conversation conditions on Earth.
• Ask questions while doing something else. Cooking, walking the dog, playing a game. Side-by-side is easier than face-to-face.
• Ask your teen questions about their life, not for a report on it. This is a big one. Please avoid turning into a detective. Adults don’t like and teens really don’t like it. “What was hard about today” gets more than “how was school.”
• Ask your teen a question, then pause and wait. Ask the question, then give your teen time to speak even if it’s uncomfortably long. Teenagers often need silence to actually answer.
• Don’t fix your teen. Just listen. If they wanted advice, they’d ask.
• Don’t turn yourself into a professor and become a lecturer. The moment a question becomes a setup, they’ll stop answering questions.

Okay. The questions.

Casual Everyday Conversation Starters

These are really great conversation starters for car rides

1. What was the best part of your school day?
2. What was the worst part of your day at school?
3. What’s something that made you laugh today?
4. Who did you sit with during lunch?
5. What’s been one big thought on your mind lately?
6. If you could skip one class every day for a week, which one?
7. What song have you had on repeat?
8. What’s a video you want to show me?
9. What’s a meme you want to show me?
10. If you didn’t have any homework today, what would you do with your time?
11. What’s something you’re looking forward to this weekend?
12. What’s the last thing that surprised you?
13. What did you eat at lunch, and was it any good?
14. Is there anything you wish I’d ask you about more?
15. What’s something small that annoyed you today?
16. If today had a title, what would it be?

Deeper Conversation Starters for When Your Teen Is Actually Talking

This is the part that most parents, including me, get really excited about. Our teen starts to talk, and we get this wild energy inside. Something close to winning a Grammy award. I want to encourage parents to slow down, not to turn into a lecturer, and not to ask too many questions.

16. What’s something you’ve been thinking about but haven’t told any of your friends?
17. What do you wish adults understood about being your age?
18. What’s a compliment that stuck with you?
19. What’s a criticism that stuck with you?
20. When was the last time you felt really proud of yourself?
21. What’s something you’re afraid of that you don’t usually talk about?
22. Who do you feel like you can be your full self around?
23. What’s a mistake you’re glad you made this month?
24. What do you wish you were better at?
25. When was the last time you had a good cry?
26. What do you do when you feel like you are doing too much?
27. What’s a decision you’re trying to figure out this week?
28. Is there anything that’s been on your mind that you want to talk about?
29. What do you wish I did differently as a parent?
30. What do you think I get right?

Questions To Ask Your Teen That Are Funny and Silly Conversation Starters

31. What’s the weirdest thing you can do with your body?
32. If you had to lose one of your five senses to keep the others sharper, which would you lose?
33. What’s the strangest food you actually like?
34. Who would win in a fight — a bear or a tiger? (Yes, teens have opinions about this.)
35. What’s the worst show you actually love?
36. If our family was a reality TV show, what would it be called?
37. What’s the most embarrassing thing that happened at school this year?
38. What’s a fictional world you’d want to travel to?
39. What’s a superpower that sounds cool but would actually be annoying?
40. If you could rename yourself, what would you pick?
41. Which part would you not give up holding?
42. What’s something adults do that you think is weird?
43. What would you do with $20,000 that had to be spent in 24 hours?
44. What’s the funniest thing a teacher has ever done?
45. If you could bring back one thing from when you were a kid, what would it be?

Questions To Ask Your Teen About Values, Identity, and “Who Are You Becoming”

46. What kind of person do you want to be in 20 years?
47. What matters to you that doesn’t seem to matter as much to your friends?
48. What are you good at that most people don’t know about?
49. What are your strongest values right now?
50. Who’s someone you admire?
51. What’s a moral question you’ve been thinking about?
52. What’s something you used to believe that you don’t anymore?
53. When do you feel the most not like yourself?
54. What’s a stereotype about your generation that you disagree with?
55. What’s something about you that hasn’t changed since you were little?
56. What do you think you’re here to do?
57. What’s a cause you care about?
58. What do you want to be remembered for?
59. What’s a tradition from our family that you want to keep?
60. What’s one you don’t?

Questions To Ask Your Teen About Friends and Relationships

61. Who are your closest friends right now?
62. Is there anyone at school you wish you were closer with?
63. Is there a friendship that’s been feeling weird lately?
64. What 3 things make a good friend?
65. What’s something a friend has done recently that surprised you?
66. Have you ever felt like you had to hide part of yourself around your friends?
67. What do you do when a friend is going through something emotionally difficult?
68. Have you had your feelings hurt recently and didn’t say anything?
69. Do you like anyone right now?
70. What do you want out of a friendship?
71. What does a healthy relationship look like to you?
72. Is there anyone whose opinion of you matters too much?
73. When you fight with a friend, do you usually apologize first, or wait for them to?
74. Is there anyone you’ve been meaning to reach out to?
75. Who do you talk to when things are hard?

Questions About School, Stress, and the Future

76. What subject actually interests you right now?
77. What’s the hardest class this semester?
78. Is there a teacher who really understands you?
79. Is there a teacher you dread?
80. How do you know if you are sleeping enough? 
81. How worried are you on a scale of 1 to 10 this week?
82. What’s something at school that’s easier than it looks from the outside?
83. What are you starting to think you might want to do after high school?
84. What are you dreading about growing up?
85. What are you excited about?
86. If you could take a year off after high school to do anything, what would you do?
87. What’s a career you’d never want, no matter how much it paid?
88. What’s something you’d want to learn that has nothing to do with school?
89. Do you feel like the future is scary, exciting, or both?
90. What’s a decision about the future that feels too big to think about?

Questions To Ask Your Teen About Mental Health and How They’re Doing

91. How have you been doing, really?
92. What’s something that’s been weighing on you?
93. When you’re really worried, what does it feel like in your body?
94. What helps when you’re feeling angry?
95. Have you ever thought about talking to a therapist?
96. Is there anything I could do differently to make it easier for you to tell me things?
97. What do you do when your thoughts get too loud?
98. Have you been feeling more tired than usual?
99. If your friend was going through what you’re going through, what would you tell them?
100. Is there anything you’ve been carrying that you want to put down?

Therapy Questions for Teens (For Counselors and Therapists)

As a counselor who works with teens, I continue to be surprised. I think one of the most important lessons teens have taught me is to never assume. To always be curious. In case you are curious, here are some common therapist-led questions. 

• First session: “What does ‘therapy going well’ look like to you?”
• Rapport-building: “What’s something about you a good therapist would know within a few sessions?”
• Assessing distress: “On a scale of 1 to 10, how are you doing today? And what’s the difference between a 4 and a 6 for you?”
• Exploring family: “If I could listen in on your family for a week, what would I hear?”
• Identity and values: “Who do you want to be, and what’s in the way?”
• Coping strategies: “What do you already do that helps, even a little?”
• Safety: (direct, non-euphemistic questions when appropriate) “Have you had any thoughts of hurting yourself or not being here? I ask everyone.” 

When Conversation Isn’t Enough

Let’s talk about what happens when you are trying over and over to speak with your teen. When you are doing your best and pulling all of the tricks, and yet, no success. As a parent, I get it. I’ve been there with my kids in those moments when the conversation is not moving forward. And you know what, it’s okay. I may not always be the right person who is going to move a specific conversation with my child. It may be the soccer coach, the teacher, or the therapist.

You may find that sometimes the answer to “how are you doing” is bigger than a car ride can hold. If your teen is showing signs that they’re struggling. That they have persistent low mood, withdrawal, self-harm, hopelessness, or a change that’s lasting longer than a few weeks, then a therapist can help.

Santos Counseling provides teen therapy in Greensboro, NC for anxiety, depression, ADHD, identity, family conflict, trauma, and everything in between. Sessions are available in person and online across North Carolina, in English and Spanish.

📞 336-663-6570 ✉️ admin@santoscounseling.com

If your teen is in crisis or having thoughts of suicide, don’t wait: call or text 988 (Suicide and Crisis Lifeline), text “HOME” to 741741, or go to your nearest emergency room.

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