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How To! with Mike Pesca

How To Raise a Boy

How To! with Mike Pesca

Peach Fish Projects

Education, How To

4.32K Ratings

🗓️ 7 October 2025

⏱️ 38 minutes

🧾️ Download transcript

Summary

Jen is raising a pretty stellar 9-year-old son. With his tween and teen years on the horizon, she wants to steer him toward kindness, acceptance, and openness—and away from the pitfalls of toxic masculinity. On this episode, How To!'s Carvell Wallace brings on Ashanti Branch, founder of The Ever Forward Club and host of unMASKing with Male Educators. Ashanti offers his advice on talking with boys about their emotions, understanding the "mask" that young men present to the world, and building trust and confidence—by acknowledging that adults don't have all the answers.

If you liked this episode check out: How To Parent Less and How To Make Friends … Like a Man

Do you have a problem that needs solving? Send us a note at howto@slate.com or leave us a voicemail at 646-495-4001 and we might have you on the show. Subscribe for free on Apple, Spotify, or wherever you listen.

The show is produced by Rosemary Belson, with Kevin Bendis and Sophie Summergrad. Our technical director is Merritt Jacob and our supervising producer is Joel Meyer.

This episode is for Slate Plus members. Join now to unlock it—plus other exclusive How To! bonus episodes and ad-free listening across all your favorite Slate podcasts. Subscribe from the How To! show page on ⁠Apple Podcasts⁠ or ⁠Spotify⁠. Or, visit ⁠slate.com/howtoplus⁠ for access wherever you listen.

Transcript

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0:00.0

Hi everyone, I'm Susie Weiss, and I've noticed there's just simply not enough podcasts in the world. So I'm launching my own. Let's go. Let's go, baby. Second Thought is a weekly show about pop culture. The stuff everyone's been binging, arguing about, obsessing over. Here's the thing about heated rivalry. I mean, even the most devoted swifties, I think we can agree, not our best work. We'll be hosting thoughtful conversations with culture's most important figures. Talk about genius.

0:22.6

Talk about generational talent.

0:23.7

Coming to headphones near you on April 17th with a first guest you won't want to miss. Available wherever you get your podcasts. A middle young man yesterday at a college, he had come from a high school situation where he was going through a lot of stuff. And he said, when I get to college, I'm going to be a new person. And he started feeling like some emotions come up. He's like, oh, man, I'm not supposed to be getting emotional here. He has sunglasses on. I can see a tear coming out behind them glasses. And I'm like, let it flow, brother. Let it flow. You're safe here. Welcome to how to. I'm Carveau Wallace.

0:56.0

What the hell is going on with men and boys?

1:00.0

This is a question that has probably crossed a lot of people's minds, at least once in the past few years.

1:07.0

And as longtime Slate listeners know, when I was a parenting and vice columnist here, variations

1:12.0

of this question would come up all the time.

1:14.9

How do I raise a decent boy?

1:16.6

How do I teach my son to be in touch with his feelings?

1:19.6

How do I rescue my son from patriarchy and misogyny?

1:23.0

How do I teach my son to respect women, to not be racist, to not be homophobic. For parents, these questions have felt intense and pressing, and even more so in the midst of news stories about school shooters, male loneliness, male violence, sexual harassment, and assault.

1:39.3

But there is another side to it.

1:43.3

Parents want to know how to raise boys that are aware of all the danger and toxicity in our culture around male identity,

1:51.2

but they also want to know how to raise boys who love and respect themselves,

1:56.1

who can have humility without humiliation, pride without supremacy.

2:01.6

It's a lot to figure out when you're holding a little innocent baby boy in your arms and thinking about his future.

2:09.6

And it's a challenge our listener knows all about.

2:12.6

My name is Jen and I am the lucky mother of a nine-year-old boy who's just the light of my life, of course. You mean like a little bit of a picture like, what's his personality like? What's he interested in? What does he like to do? What lights him up? Tell us a little bit about him. Yeah, you know, he loves his friends. He's outdoors. He likes to play sports. He certainly loves video games too. He recently told me he wanted to be a stand-up comedian. So yeah, he's pretty outgoing. He's, you know, pretty respectful around adults. He's a great guy. He really, really is. But, you know, he's getting to those pre-teen years and I always worry, you know, what direction could he go in? Like, how can I help him to grow to be,

2:53.1

like, a happy, healthy, confident person? Does he seem like a healthy, happy, confident person now?

2:59.7

Generally, yes. Of course, he has his moments when I can feel the pang of, you know, his self-doubt,

3:05.1

or maybe he'll speak badly about himself. And, you know,

3:08.4

I think the worries I have are the same, probably as most parents, you know, having them be

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