Questions to Ask a Teenager
Low-pressure questions for talking to a teenager you do not know well, or one who answers everything with one word, arranged from easy openers to the ones worth saving.
The questions
Open any question for the note
What have you been watching lately?
Why ask it
The most reliable opener there is, because it costs nothing to answer and they are usually mid-way through something. The mistake is asking and then saying you have never heard of it, which ends the exchange instead of continuing it.
What are you listening to at the moment?
Why ask it
Works even when nothing else does, and it gives you something to come back to weeks later. Ask them to play you one song rather than describing it, and say something specific about what you heard, even if it is not for you.
What is something you are into that nobody else here cares about?
Why ask it
Gives permission to talk about the niche interest they usually keep quiet, which is where genuine enthusiasm lives. Expect something you know nothing about, and let them explain it at length without checking whether it is useful.
What is the best thing you have seen online this week?
Why ask it
Better than asking about their phone use in general, which sounds like the start of a rule. If they show you something, laugh at it if it is funny and do not ask them to explain why it is funny if it is not.
What did you actually do at the weekend?
Why ask it
The word actually signals you want the real answer rather than the summary. Follow up on details rather than the shape of it: who else was there, whether it was any good, what they would do differently.
What is the best thing that has happened today?
Why ask it
Far better than asking how their day was, because it asks for one specific item rather than a verdict on seven hours. On a bad day it also lets them tell you it was nothing, which is information in itself.
Who is the funniest person you know?
Why ask it
An easy question that quietly maps their friendships, since the funny person is usually someone they like being around. It also tends to produce a story, which is more than you get from asking who their friends are.
Which teacher would you keep, and which would you replace?
Why ask it
The complaint half is what makes the compliment half honest. You will learn what they respond to in an adult, which is usually fairness and being taken seriously rather than any subject in particular.
What is the most useless thing you have been taught?
Why ask it
Lets them be scornful about something safe, which is a relief for a teenager mostly asked to be positive about school. Do not defend the curriculum. The point of the question is that you are not the person marking them.
What is overrated?
Why ask it
Short, open, and it produces opinions rather than facts. The answer often reveals what they are being told to like, by school, by their family, or by everyone their age, and disagreeing with it out loud is part of how they work out what they think.
What is something you are better at than most adults?
Why ask it
A genuine reversal, and they can usually name something within seconds. Ask them to show you rather than describe it, and let them teach you badly without correcting the way they explain it.
What are you looking forward to in the next month?
Why ask it
The near horizon works better than asking about the future, which for many teenagers is a stressful subject. If there is nothing at all in the next month, that is worth noticing quietly rather than commenting on.
What would you learn if lessons were free and nobody graded you?
Why ask it
Removes both cost and assessment, which is most of what makes learning unattractive at this age. The answer is worth remembering, because it is often achievable and rarely what anyone has offered them.
If school stopped tomorrow, what would you spend your time on?
Why ask it
Not a question about laziness, though the first answer may be a joke about sleeping. Wait past that. The second answer tends to be the real one and usually involves making something or being with particular people.
What is the strangest opinion you would defend?
Why ask it
Framed as a game, so it invites argument without any real stakes. Take the position seriously and push back a little. Being disagreed with respectfully by an adult is rarer for them than either agreement or dismissal.
What is something you have changed your mind about?
Why ask it
Treats them as a person with a developing view rather than a fixed set of opinions. It also models something worth modelling, so be ready to answer it yourself with a real example rather than a flattering one.
What do you wish adults asked you instead of how school is going?
Why ask it
You are asking them to write the question, and they usually can. Whatever they say, use it next time, because a teenager who watches you take that instruction is more likely to answer the next thing you ask.
What is the story people always tell about you that you are tired of?
Why ask it
Families keep repeating stories about a version of a child that is several years out of date. Being asked about it is often a relief, and it tells you exactly which old label to stop using.
What do you think you will be like at twenty-five?
Why ask it
Speculative rather than a demand for a plan, which is why it lands better than asking what they want to do. Answers about the kind of person they hope to be are more revealing than any answer about a career.
What should I know about you that does not come up?
Why ask it
Save it for a point where the conversation has been going well. It is an unusual thing to be asked, and it works precisely because it hands over control of the subject. A shrug is an acceptable outcome; the question still registers.
How to use these questions
Practical guidance for the conversation itself
Getting the timing right
- Ask while something else is happening: driving, cooking, walking, queueing. A conversation with nothing else in it feels like an appointment.
- Avoid the first ten minutes after school or a shift. Almost nobody talks well when they have just walked through the door.
- Two questions is a conversation. Six is an interview.
- Late evening is often the best window, and it is why so many real conversations with teenagers happen when you wanted to go to bed.
What makes them keep talking
Follow the detail, not the topic
When they mention a person, a game or a place, ask about that specific thing rather than moving to your next question. Interest in the particulars is what distinguishes a conversation from a survey.
Let them be the expert
Being asked to explain something they know well, and then listened to without being hurried, is uncommon for a teenager talking to an adult. It also means the next conversation starts from a better place.
Answer your own questions too
These work far better as an exchange. Give a real answer, including an unflattering one, rather than a version designed to be instructive.
Things that end the conversation
- Judging their taste in music, shows or people, even lightly.
- Turning an answer into advice, or into a comparison with yourself at that age.
- Asking a follow-up that is clearly checking up on them rather than interested in them.
- Repeating what they told you to other family members.
- Pushing when the answer is a shrug. Leave it and come back another day.