Listener Q & A: Getting Curious & Motivating Boys

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How, exactly, does one “get curious” about their son without badgering him?

That’s a big, important question, and that’s exactly what Jennifer wants to know:

Lately, as he is resisting my normal questioning…I feel like I am now pushing him to evaluate his feelings, talk to me, or just engage…I have seen this cute, fun challenge of showing a person two pieces of paper. Each one has something different written in it. The recipient who is choosing the paper has no idea what is on the other side. At one time, this fun way to choose an adventure with me would have been exciting. Today was the exact opposite. He whined, then slithered down in his seat. Covered his face. I was taken aback. So I “got curious”. I asked him what was he feeling. “I don’t know”. I asked him if he thought I would put something un-fun on them. “I don’t know.” Why. Are you feeling like a lack of control? “I don’t know”.  I probed a bit more, but you get the idea…

Well-meaning mom + fun idea + teen boy = Disappointment & discomfort

Timing may have been part of the problem. When talking to teenage boys, it’s best to avoid after-school surprises. It’s better to give them a heads-up; let them know, in advance, that you want to talk with (or do something) with them – and then, together, figure out good time.

And as for getting curious, Jen reminds listeners that “getting curious” can be internal. Instead of interrogating your son, get quiet. Think about what might be going on under the surface. Read, listen, and learn about what may be going on with your son.

Other questions we address include:

My son had undiagnosed learning differences for many years. We have changed schools a few times, but his motivation is at an all-time low…I read in a lot of literature that kids often lack motivation because of their relationship with their parents. We generally have a good relationship, but we worry that he still feels we failed him all those years ago…


 I get calls from the school that my boys misbehave…They usually get a consequence at school. How harsh should I follow up at home, do they need a second punishment?


If my junior has a winter dance coming up, and I think he should go, can I make him go or bribe him, or is this me living vicariously through him?

and also:

I’d like to hear something about the “other” teens. The ones who hide their insecurities behind perfection…So growing up they miss out on opportunities, camps, jobs… How do I help them become more confident? How do I help them see their value, take initiative and try new stuff?


I’m reluctant to let my kid go to summer camp… nervous… and how do I actually GET him to go?

Note Jen’s sweater – it’s a rental from Armoire, one of our sponsors!
In this episode, Jen & Janet discuss:
  • Why teenage boys don’t embrace (& often reject) our ideas
  • The importance of real self-care
  • Managing fear & guilt
  • Boys’ motivation
  • Responding to misbehavior & phone calls from school
  • Perfectionism
  • Summer camp & separation anxiety
Links we mentioned (or should have) in this episode:

Boost Boys’ Motivation– our online course

Listener Q & A: Punishment, Teenage Boys, & Letting Go — Q & A from late 2023

Needed: Boy-Friendly Schools — ON BOYS episode

Debt Free Mom Discusses Family Finances –– ON BOYS episode

Emails & Phone Calls from Teachers — ON BOYS episode

Sleepovers, Camp, & Separation Anxiety — ON BOYS episode

Building Boys Bulletin — Jen’s Substack newsletter

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