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Fourteen Talks by Age Fourteen: The Essential Conversations You Need to Have with Your Kids Before They Start High School

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By Michelle Icard — 2025

Trying to convince a middle schooler to listen to you can be exasperating. Indeed, it can feel like the best option is not to talk! But keeping kids safe—and prepared for all the times when you can't be the angel on their shoulder—is about having the right conversations at the right time. See more...

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The way you approach a hard conversation either reinforces a pathway for exchange or erodes trust in the relationship. You can set yourself up for a more productive, less volatile exchange by being clear about what you are trying to accomplish by treading into challenging terrain.

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Ezra Klein Interviews Anna Sale

A hard conversation is about trying to sort of understand more focus on descriptions and sharing experience but not wrapping it all up neatly at the end because when you try to do that, you’re sort of pushing through what actually is the hard thing

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How to Make Your Small Talk Big

We’ve forgotten how to talk to people. . .Our entire social lives have become a middle school dance: unrealistic expectations in the lead-up, self-conscious regrets in the aftermath.

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EXPLORE TOPIC

Helping Children Deal with Emotions