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01 · Personal & Relational

Questions to Ask Boys About Girls

Questions for a parent, teacher, coach, or mentor talking with a teenage boy about girls, friendship, and how he treats people. They start with everyday observation and move towards consent, group behavior, and what he does when something is said in front of him.

20 questions · each with a note on why · conversation guide

The questions

Open any question for the note

  1. Who are the girls you spend the most time around?

    Why ask it

    A neutral opening that gets names and settings rather than opinions. It also tells you whether his social world includes girls at all, which changes which of the later questions are worth asking.

  2. Is there a girl you find easy to talk to, and what makes it easy?

    Why ask it

    Asks him to describe something that works instead of something that worries him. The answer usually names a behavior, that she is funny or does not make it awkward, which he can then recognize in himself.

  3. What is different about hanging out with a group of girls?

    Why ask it

    Invites observation rather than a judgment about what girls are like. Answers about volume, subject matter, or how disagreements get handled are often surprisingly precise.

  4. Do you feel like yourself around girls, or does it take effort?

    Why ask it

    Names the self-consciousness most boys this age feel and rarely get asked about. An answer that it takes effort is an opening, not a problem, so resist reassuring him too quickly.

  5. What do you and your friends actually talk about when girls come up?

    Why ask it

    The word actually does the work. Expect a filtered answer first; the honest version usually arrives later in the conversation or on a second occasion, so do not react to the first one.

  6. What gets said about girls when no adults are around?

    Why ask it

    Asking about the group rather than about him makes it answerable, since he is reporting rather than confessing. It is the most direct route to the norms he is actually living inside.

  7. Have you heard something said about a girl that you did not agree with?

    Why ask it

    Assume yes, and ask what it was before you ask what he did. Jumping straight to what he did makes it a test, and he will give you the answer he thinks you want.

  8. What made it hard to say anything at the time?

    Why ask it

    A better follow-up than asking why he did not speak up. It treats the social cost as real, which it is, and gets you to the specific fear: looking soft, losing a friend, being next.

  9. What would make it easier to say something next time?

    Why ask it

    Moves to planning rather than blame, and boys often produce workable answers: saying it later and privately, changing the subject, one line they can have ready. Practicing the actual words helps.

  10. Do you think girls at your school get treated differently by teachers?

    Why ask it

    Asks him to notice a system rather than defend himself. Whatever he says, it shows how much unfairness he registers, and it is often more than adults assume.

  11. What do you see boys do online that they would not do face to face?

    Why ask it

    Group chats, ratings, forwarded images. Asking about the gap between online and in person is less confronting than asking what he has done, and it usually gets you the real picture.

  12. What would you do if someone sent round a photo of a girl at your school?

    Why ask it

    Concrete and likely. It lets you talk about what forwarding means, legally and personally, before he is standing in it with a phone in his hand.

  13. Where do you think you learned how to treat girls?

    Why ask it

    Look for what he names: home, friends, films, whatever he watches. It shows you who else is teaching him, and it is a fairer question than asking who told him something wrong.

  14. If you liked someone, how would you go about it?

    Why ask it

    Practical, and it often reveals a plan built on a film. This is the point where a specific suggestion from you, ask her in person and not through friends, is genuinely useful.

  15. How would you know whether she wanted to be asked out or just wanted to be friends?

    Why ask it

    Teaches him to look for signals rather than decide. Answers built on hints and hearsay are worth replacing with the plain version: you ask, and you accept the answer.

  16. What would you do if she said no?

    Why ask it

    The most important question here. Rehearsing a graceful response in advance makes it far more likely on the day, and an answer involving persistence needs to be corrected clearly and without shaming him.

  17. Has a girl ever told you something that changed how you saw things?

    Why ask it

    Invites him to credit a girl as a source rather than a subject. If he has nothing, that is worth noticing quietly rather than remarking on.

  18. Who do you talk to when something goes wrong with a girl?

    Why ask it

    Tells you whether he has anyone at all. Boys this age frequently name nobody, and a name he trusts, even if it is not you, is a better outcome than the conversation ending with you.

  19. What is the hardest part about being a boy your age around girls?

    Why ask it

    Gives him room to say something honest about pressure, appearance, or fear of getting it wrong. Take the answer seriously; correcting it immediately teaches him not to answer again.

  20. Is there anything you have been wondering about that you have not been able to ask anyone?

    Why ask it

    A closing question that often produces the real one, sometimes minutes later or the next day. Say you will answer it straight, and then do, even if you have to look something up first.

Having this conversation with a teenage boy

Practical guidance for the conversation itself

Set it up so he can actually talk

  • Have it side by side rather than face to face: in the car, walking the dog, washing up. Eye contact raises the stakes for most boys this age.
  • Ask two questions, not twenty. This works as several short conversations over months, not one long sitting.
  • Expect one-word answers at first and do not fill the gap. A pause of a few seconds is where the second sentence comes from.
  • Say at the start whether anything he tells you stays between you, and then keep to it. If there is a limit, safety, say what the limit is.

How you respond decides whether he answers again

Do not lecture the answer

If a lesson follows every honest reply, he learns to give you the tidy version. Say thank you for telling me, ask one more question, and come back to your point another day.

Correct the behavior, not the boy

There is a real difference between that is not okay to say about someone and you are the kind of person who says that. The first can be accepted; the second gets defended.

Do not repeat it to other adults

If what he tells you turns up in a conversation with his mother, his coach, or a friend's parent, the door closes. Ask him first unless someone's safety is involved.

Answer his questions honestly

If he asks something factual about bodies, sex, or the law, answer it plainly or say you will find out. Evasion sends him to whatever his phone tells him instead.

Worth being specific about

  • Asking, and accepting the answer. Give him the words for both asking someone out and hearing no.
  • Forwarding images. Say clearly what sharing a photo of someone can mean for the girl and for him, including legally where you live.
  • Bystander lines he can actually use, short and low cost, said in the moment or quietly afterwards.
  • That a girl being friendly is not a signal, and that he is allowed to ask rather than decode.

If it goes nowhere

  • Silence is not refusal. Boys often answer a question days later, in the car, out of nowhere.
  • Try the question about his friends rather than about him. Reporting on a group is much easier than talking about yourself.
  • If something he says worries you seriously, involving a school counselor or his doctor is reasonable, and telling him you are doing it is better than doing it quietly.
  • Make sure he knows the door stays open, and say it once rather than every week.