Questions to Ask Your Son
Questions for parents of school-age boys and teenagers, built to get further than "how was school." Ordered from everyday openers to the harder subjects, with notes on age and on when to ask.
The questions
Open any question for the note
What was the funniest thing that happened today?
Why ask it
Works where "how was school" fails because it asks for one specific moment rather than a summary. Humour is also the topic boys are most willing to open with.
Who did you sit with at lunch?
Why ask it
A factual question about a moment you can picture, which is why it gets an answer. Over weeks the names tell you far more about his social life than asking about friends directly.
What's the best and worst thing about your day?
Why ask it
The paired format matters: giving him a slot for the bad part means he does not have to decide whether to raise it. Ask in that order so the conversation does not end on the low note.
What are you into at the moment?
Why ask it
Present tense and low stakes, and it lets him talk about a game, a sport, or a video channel without being assessed. Listening to the whole answer is what earns the harder questions later.
Can you teach me how that works?
Why ask it
Reverses the usual direction and is often the fastest route to a long conversation. Let it be genuinely his subject, and do not turn the explanation into a lesson about screen time.
What's something you're good at that nobody's noticed?
Why ask it
Sons are frequently praised for the visible things, grades and sport, and rarely for the rest. The answer tells you where recognition is missing.
What's the most annoying rule at school?
Why ask it
Complaining is easy, and the specifics usually reveal how the place is run and how he handles authority. Resist defending the school, or the tap turns off.
Who in your year would you not want to be?
Why ask it
Safer than asking who is unpopular or bullied, because it is about him. Answers often describe the social risk he is trying hardest to avoid.
What do your friends worry about?
Why ask it
Asking at one remove gets answers where asking directly gets a shrug. What he attributes to friends is usually a fair guide to what is on his own mind.
Is there anything going on with your friends that's stressing you out?
Why ask it
Friendship trouble is more common and less reported in boys than academic trouble. Name it as stress rather than as feelings, which lowers the cost of admitting it.
What's something you're finding hard at the moment?
Why ask it
Neutral phrasing invites schoolwork, sport, or people equally. Do not solve it in the same breath: ask whether he wants help or just wanted to say it.
Do you want advice, or do you just want me to listen?
Why ask it
Worth asking every time. Most conversations with teenage sons collapse at the moment a parent starts offering solutions to something that was only being reported.
What do you wish I understood about your life?
Why ask it
Puts him in the position of explaining rather than defending. Expect it to be about pressure, time, or how much of his world happens online.
What's something I do that winds you up?
Why ask it
Asking directly, and then not arguing with the answer, does more for the relationship than any other question here. He will test whether you can take it before he tells you the real one.
Who do you go to when something's wrong?
Why ask it
If the answer is not you, that is useful rather than wounding: it tells you who is actually in his corner. If the answer is nobody, that is the thing to work on.
What kind of man do you want to be?
Why ask it
Better asked in the car or on a walk than across a table. Answers are usually about how he wants to treat people rather than about a job or a status.
Where do you get your ideas about how men should behave?
Why ask it
Names the influences without attacking them, which is the only way this conversation stays open. Expect a mix of friends, sport, family, and people he follows online.
Has anyone online ever said something to you that felt off?
Why ask it
Deliberately vague so it covers strangers, groups, and money as well as anything sexual. Keeping your reaction flat is what determines whether he tells you the second time.
If you got into real trouble, would you tell me?
Why ask it
Ask it in advance, not during a crisis. A hesitant or honest no is the most valuable answer you can get, because it tells you what needs to change before it matters.
What would you want to do together, just us?
Why ask it
Ends with something to arrange rather than something to discuss. Side by side activities produce more conversation with sons than any question asked face to face.
How to use these questions
Practical guidance for the conversation itself
When to ask
Sideways, not face to face
In the car, on a walk, doing the washing up, playing something together. Sons talk more when eye contact is optional and there is an exit from the conversation.
Not the moment he walks in
Straight after school is the worst window for most boys. An hour later, or at bedtime, gets a different quality of answer entirely.
One question, then stop
A single question and a genuine pause beats four in a row. If he gives you one word, let it go and come back another day.
Answer it yourself first sometimes
Telling him the worst part of your day makes the same question askable. It also shows that admitting difficulty is normal rather than a failure.
Adjusting for age
- Five to eight: keep to today and to concrete moments. Funniest thing, who he sat with, best and worst part.
- Nine to twelve: fairness, rules, and friendship politics are live subjects, and he will talk about them at length.
- Thirteen to fifteen: expect shorter answers and more privacy. The questions at one remove, what friends worry about, work better than direct ones.
- Sixteen and up: he can handle the questions about what kind of man he wants to be and where those ideas came from. Treat him as someone with a view rather than someone to be shaped.
- At every age, the question about whether he wants advice or just to be heard applies.
Common mistakes
Turning the answer into a task
He mentions a hard test, you produce a revision plan. Do this a few times and he stops mentioning things, because reporting a problem now costs him something.
Reacting to the disclosure you asked for
If you asked about something online, or about trouble, your face in the first two seconds decides whether he tells you again. Deal with your alarm afterwards.
Using the question to make a point
"What are you into at the moment?" followed by a comment about screen time is not a question, and he will recognise it as an opening move.
Interpreting silence as nothing
"Fine" and a shrug are often a request for a lower-stakes question, not a refusal. Try something factual and specific instead of something broader.
Asking only when something is wrong
If real questions only appear after a bad report or an incident, they get heard as an investigation. The everyday ones are what make the serious ones possible.