Dear Rosalind, I recently had the opportunity to read your work, particularly Owning Up: Empowering Adolescents to Create Cultures of Dignity and Confront Social Cruelty and Injustice, and was genuinely impressed by its clarity of purpose and the strength of its educational and social insight.

What stood out most was the way you translate complex and often sensitive social issues into practical, research-informed strategies that can be used by educators and students alike. The balance between theory, real-world application, and interactive methods such as role play and discussion-based learning gives the work both authority and accessibility. Your emphasis on dignity as a guiding principle throughout adolescent social experiences feels especially timely and impactful.

I would be very interested in learning more about your current writing plans… And I would be pleased to direct any further publishing related correspondence through your agent.

For two weeks I walked around thinking this was real. I’d even confirmed that the person exists and really does hold that position at the named publishing house. But the rest was a lie.

One of my least favorite emotional journeys is the moment when time slows and you feel self-conscious, embarrassed, and naïve simultaneously.

In retrospect there were obvious signs I should have caught. But there were also signs it was real. The email looked real, and the company link in the signature went to the actual publisher. (I know that means nothing — anyone can hyperlink whatever they want in an email — but it fooled me in the moment.)

I was also tricked because whoever wrote it intuited that the way to get my attention wasn’t telling me how much they loved Queen Bees or Mean Girls. Instead, they praised Owning Up, my social-emotional learning curriculum. All of my writing is a labor of love, but Owning Up has been a long-term commitment for a visibly smaller reward. It’s the writing I’ve worked hardest on that is least publicly known. Being seen for that felt different. It felt like being understood.

I was vulnerable for another reason, though I didn’t fully realize it at the time. Months ago, I posted on IG and LinkedIn that I was writing a new book. Announcing that you’re writing a book before you have much to show for it was terrifying. It meant I was making a promise, to other people and to myself, when nothing about the book was firmly in place. To declare “I have an idea” before the idea is finished, or in my case not even really started, is taking a huge risk. What if I couldn’t write it? What if the journey I’m sharing turns out to be a story of not following through?

Since then, more “people” have written to me with similar pitches, making me stop and think about some bigger questions. Why do people try to take advantage of us when we are feeling so vulnerable? How can they tell? And how can WE be aware that we have now entered this vulnerable place so therefore are likely to be targeted?

We can’t live without being vulnerable at least some of the time. Or can we? Not performative vulnerability or “authenticity,” but really sharing how we feel about something that happens to us?

It’s also made me think about how to respond to young people who write to me for advice. Do I start assuming that every person who reaches out to me is lying? Or do I create hoops people have to go through to prove to me they are real?

I can’t live like that, but I can’t expose myself foolishly either. So here’s what I’ve decided.

I’m going to keep admitting my vulnerabilities and my mistakes, to everyone but especially to young people. For example, I can say that in the last few days I went back with my team and we found several other phishing attempts under the guise of speaking requests. So we now have safeguards protecting me and the people I work with. Maybe even saying that will invite more attacks against us, but I don’t want to live always assuming the worst of people. I want to live with the belief that vulnerability is a path to greater connection with others and having a more meaningful life.

I also think adults owe young people this story, not as a warning dressed up as relatability, but as evidence. Evidence that we go through this too. Not to prove we’re just like them — we’re not, and we don’t need to be. Just so they can watch an adult get fooled, feel embarrassed, take a breath, step back, and figure out what to do differently. That’s the whole point. Not that we’re immune. That we learn from our moments of weakness and don’t become bitter and paranoid, but aware and take care of ourselves.

We don’t grow out of wanting to be seen and understood, no matter what age we are.

Has something like this happened to you? I’d love to know what happened, how you handled it and the lessons you learned.

We live in two worlds at once: one where we talk about boys and what’s wrong with them, and another where we try to talk to boys and wonder why they won’t talk to us.

Boys don’t trust us. And they have good reason not to.

When I wrote Masterminds and Wingmen twelve years ago, over 150 boys critiqued every description of their world and every piece of advice for navigating it. Even then, I was watching adults tear boys in two directions at once…and congratulate themselves for it. On one side was the alpha trap: a caricature of masculinity where a boy’s worth is measured by constant displays of self-assurance, getting rich, contempt for anything “soft,” and dominating any debate about culture or gender. On the other was the compliance trap: where boys were expected to agree, without question, that they somehow personified that caricature, where any question, any “but what about...” was treated as evidence that they already were.

Both failed boys. Both alienated them from the people they most wanted to believe in; their parents, families, teachers, coaches. We told ourselves we were helping. We weren’t. Some of those boys are now becoming fathers themselves. And our answers haven’t gotten better.

Today, it’s worse. Ideas once confined to dark corners of the internet are mainstream, and they’ve trickled down to the youngest teens. Andrew Tate of course was the first and most obvious voice of this movement but now its influencers have built global empires out of selling powerful messages of financial, social and cultural domination. The message to boys is the same across all of it: financial success at all costs, never appear weak, and interactions with girls are about asserting control.

But the counter to it has gotten more extreme too. I’ve lost count of the boys who’ve told me how it feels to disagree with an adult or a girl on the other “side” and get shut down, as if the question, and he as the one asking it, is the problem.

I know this because it happened in my own family. My youngest son, around 18, began expressing political views different from mine and my husband’s. We questioned his sources. We jumped to assumptions. And we started to see we were at risk of damaging our relationship with him through our own refusal to listen. We had a great deal to learn from him and continue to do so.

My son isn’t alone. This is what 15 year old Oliver recently shared with me:

There’s no way out. Say the wrong thing to girls and they gang up on you. Disagree with the teacher about how bad sexism is and you get a bad grade. Disagree with your coach if he calls you a p**sy, same thing. So you say whatever causes the least problems and keep your mouth shut.

No matter what “side” we’re on, boys believe we’ve already decided how they should think, act, and speak — so they protect themselves behind the “I’m fine,” the detached shrug, or the “right” answer, unwilling to hand us more ammunition for our lectures.

Which is exactly why understanding their world, and for fathers, remembering it matters so much. The thing adults forget about Boy World is how much boys’ friendships matter to them, and how their role in their friend group shapes their daily lives.

When our kids are little, we are how they make sense of the world and their place in it. As they get older, their center of gravity naturally shifts from parents to peers. When something goes wrong with us, with school, with girls they bring it back to that group and process it there. Which means if we want to understand boys, we must understand how those groups really work.

Most fathers understand this, even if they haven’t thought about it in years — which friend they could actually talk to, which friendships required performance, the roles they didn’t choose and couldn’t escape. Those same dynamics still shape their sons: a tight inner circle where boys can be themselves, and a wider one where they fall into predetermined roles, no matter where they live or what school they attend.

Among these roles is the Punching Bag, loved by the group and relentlessly mocked by it. They protect him from people outside the group but go after him constantly themselves. As one student put it: he’d rather be miserable than alone. Then there’s the Fly; hovering on the outside, desperate to belong, unable to see how unwelcome he is. As one boy told me bluntly: “We don’t like him. We use him. Parents can’t see it when their kid is like this, especially when they have money — they try to buy our friendship for him.” And then there are boys with no group at all, desperate for the belonging that everyone around them seems to have found without effort.

These are the boys the manosphere was built for.

Andrew Tate and others didn’t invent Boy World. They just learned to weaponize and monetize it. They found the Punching Bags and the Flies and the boys with no one — and offered a tailored message to each. For the Punching Bag: the friends who mock you aren’t your brothers — they’re beneath you. For the Fly: you’re not unwanted, you’re surrounded by people too mediocre to recognize your value. For the boy with no group: we are your group now. In each case, the diagnosis is wrong, but the wound is real and that’s what makes it work.

Buy in, and you move from the outside of the group to the top of it.

These are extraordinarily seductive offers to boys who have spent years being used, ridiculed, judged, or ignored. The boys most at risk aren’t confused or broken — they’re responding rationally to years of feeling unseen. Which means the entry point isn’t correction. It’s curiosity.

The antidote starts with stopping. Stop talking, stop explaining, stop judging, and stop assuming you already know what your son thinks about these influencers. Every boy needs an adult he doesn’t have to hide from; someone who takes his questions and fears seriously, and understands how much he is shaped by his social world. That relationship is more powerful than anything he’ll find on a screen.

For a father, or any adult, this is less about intervention and more about the relationship he already has. It starts with asking “Why do you like that guy?” instead of “I can’t believe you watch this guy.” and actually listening to whatever comes back. A father who flinches or lectures won’t get a second conversation; one who catches himself, apologizes, and asks for a redo probably will. Fathers also know from their own boyhood what it means to be with friends without an agenda — that time still matters for their sons, and protecting it rather than filling it is essential. When it comes to choosing a coach or a team, the question isn’t which league has the best record . It’s which adults model what it looks like to be strong, fair, and genuinely demanding. Boys know when a man actually believes what he’s asking of them. And they know when they’re being managed instead.

Father’s Day is a moment to recognize everything dads do for their children. But the father I started with, the one whose son barely speaks to him now, already has what he needs to find his way back. He knows what it felt like to want a relationship with his father where he was really seen. He knows what his male friendships meant to him, what they gave him and what they cost him. The question isn’t whether he has the tools. It’s whether he trusts those memories enough to walk back into that world with his son and become the person his son doesn’t have to hide from.

Rosalind Wiseman is the author of Masterminds and Wingmen and Queen Bees and Wannabes. She is currently writing The Adults Our Children Need with a group of young people.

Graduating is supposed to be a celebration. But every conversation at the ceremony felt like sitting in the hot seat. "Where do you want to go? What’s your dream job? What are you studying? What do you want to do? Have you thought about internships? I know of a great program you might be interested in..." It never ends, and with each question, the dread increases. I've changed my major three times. Every choice felt impossible — not viable because of AI, or impossible financially in the current moment. It's hard to answer with a polite smile when you're a mess on the inside, reminded of everything you still have to figure out. But adults don't see that. All they see is a young person, fresh out of high school, with a bright future ahead of them — a future like the one they had. A future that died years ago.

-Naomi, 18

Naomi is eighteen, and part of a group of young people I work with. The adults at her graduation meant well. But meaning well is not the same as paying attention. When we ask these questions “What are you studying?” “What’s your plan?” “Have you thought about internships?” We think we’re showing interest. We’re not. We’re proving to young people that we have no idea what it actually feels like to be standing where they are.

Even before AI, young people have always known what these questions are really asking: assure us that you are a young person that we approve of. That they are meeting the expectations we have of them. The child who wanted to be a writer learned to say “communications.” The one who wanted to build things with her hands learned to say “engineering.”

Young people notice which dreams get an approving smile and which get suggestions toward something more seemingly stable, something with clearer earning potential. Many of them are aware of the sacrifices their parents and grandparents made to give them what they have now. They don’t want to disappoint us.

That was always the quiet damage of these questions. Now it’s worse.

We got a glimpse of how much worse this spring, when graduation speakers across the country told students that AI was an exciting opportunity, a reason for optimism — and students booed. This happened repeatedly, at school after school. Adults, especially the graduation speakers, were surprised. Some of them were even patronizing. Listen to some of the other young people I work with:

“Honestly, AI terrifies me. Yes, it is a tool that can be used for good, yes it can simplify things, but it is not just good things. I have seen friends of mine have to switch their major because it was a ‘dying field due to AI.’ This fills me with angst since it shows that humans are turning towards AI — cheaper, quicker, more efficient — instead of supporting other working individuals. So how long will it be until it takes over our jobs? And humans are becoming very dependent on AI, their independent critical thinking is decreasing due to relying on it. So what will happen when our future doctors, lawyers, rely on AI to do their jobs — is this an advantage or a liability?” — Alessandra, 17

But the fear isn’t only about jobs disappearing. Another described something harder to name — a kind of identity erosion:

“ChatGPT has become my teacher, mentor, advisor, therapist, and a place where I can share my thoughts. It knows a lot about me because I use it to share everything. However, this also worries me. If I rely on AI so much, I sometimes wonder what I would be like without it. If I am still able to think, make decisions, and be confident for my life. AI helps me a lot, but it also makes me question where my own value begins and where the help of AI ends.” — Yueyu, 17

Monte, 16, described watching this happen in real time, in himself and his peers: “Prior to AI I’d say I was a very creative thinking individual. But now that I am more dependent on it to complete tasks, I also think that I don’t have anything assured. So there is never a safety net I’d say to choosing a job that I would like but also be able to accomplish my wishes, without AI taking over it in the next 10 years.”

Research is beginning to confirm what these young people are already describing in themselves. An April, 2026 EdWeek survey found the most common emotions Gen Z associates with AI are now anger and anxiety — and the least common are excitement and hopefulness.

We need to ask questions that show our care, curiosity and our wisdom: three things young people desperately need from us right now. Here are five ways to open a real conversation instead:

“I have no idea what it would be like to be growing up right now. What do you think is important for me to understand?” Recognizing that it is truly different growing up today than when you did is the single most important thing you can say to a young person right now.

“I didn’t really know what I wanted to do when I went to college. I’d imagine it’s even more complicated today. Am I getting that right?” Acknowledging that you didn’t know what you wanted to do when you were their age makes room for their truth instead of a performance.

“What do you think our family expects of you as an adult, and does that fit with what you are curious about or how you want to contribute?” This gives them an opportunity to name the family’s spoken and unspoken expectations and opens the door to understanding how they want to live their own values.

“What worries you most about the future?” They’re already worried. Being asked directly, by a calm adult who can sit with the answer, is one of the most useful things you can offer.

“What would feel like a good life to you?” Not a good career — a good life. Because these are not the same thing, and we conflate them constantly.

Not one young person I’ve spoken to used the word happiness when talking about their future. I think it’s because happiness has been sold to them as the absence of struggle, disappointment and failure. That is not what happiness is and they know it.

A good life, a genuinely happy one, looks more like this: contributing to something larger than yourself. Having room to create and stay curious. Pursuing something you can be proud of, even without a guarantee of success. Finding meaningful connections with other people. And having somewhere to pause, find peace, and reflect.

None of that requires knowing your major at seventeen, or being certain about your future in a world where that is impossible to know anyway. All of it requires adults who ask better questions.

And that is exactly the point. Young people don’t need us to have the answers and we don’t have them about AI or anything else. They need us to meet them where they actually are; to be honest about what we don’t know, and ask better questions that show we are curious and brave enough to face the future with them.

Subscribe now

Young people tell me things all the time that stop me cold; something so clear-eyed and true that I think, of course. How did I not see that?

Sharing the insights I get from young people is what this place is all about.

For more than 25 years, I’ve been invited into conversations with young people that are nearly impossible to have; listening to what they actually think and feel, then turning around and telling the adults in their lives what they’re missing.

Some of you know me from Queen Bees & Wannabes, which became the film Mean Girls, or Masterminds & Wingmen. Those books were about what happens between young people. This Substack is about what happens between young people and the adults who parent, teach, guide, and mentor them and why those conversations can be frustrating or baffling.

Young people tell me things they hide from adults. Part of why that happens is that I’m not an adult who can get them in trouble or they can disappoint. But I’ve also built the expertise to listen in a way that makes young people feel acknowledged and respected. I ask them to tell me when I’m getting it wrong. They review and challenge everything I write. That’s not a performance or a courtesy. It’s how I know what I know.

Here’s what that access has taught me: behavior that looks irrational from the outside almost always makes complete sense from the inside. Young people have a clear logic. They just can’t always tell you what it is or they’ve decided you can’t handle it.

At least every two weeks, I’ll share something young people are telling me that gives you insight into their world or a different way to see a problem. Then I’ll walk you through how to talk to them; the right approach, what they’re afraid you’re thinking about them, how to recognize when the conversation is going off the rails, and how to repair it. And sometimes the most important thing you can do is leave them alone until they’re ready to come to you.

This isn’t about tracking slang or the latest fad. It’s about the how of building real relationships with young people, and having the conversations that count when they’re the hardest to have.

Obvious in Retrospect is for parents, educators, coaches, and anyone who works with or loves young people and wants to understand them better. Each article is drawn from what I’m hearing directly from young people all over the world — and from the adults who are trying, sometimes desperately, to reach them.

I’m also using this space to think out loud about the ideas in a new book I’m writing — with young people, not just about them.

I’m glad you’re here.

Rosalind

Subscribe now