Withholding and withstanding judgment in the age of AI

Connection requires grace

Last fall, I cried on stage at a conference. It wasn’t planned or performative. I didn’t even realize it was happening until I was midway through a sentence and felt my chest start to tighten.

The point I was trying to make—before my eyes filled with tears and my voice gave out—was this: young people feel judged when they talk to adults about AI. And that matters, because when people feel judged, sycophantic AI starts to look like a safe and seductive alternative.

That creates a Catch-22, especially for parents, who, almost by definition, are going to judge our children. It’s our job to help them. And yet “helping” so often comes laced with assumptions about who they should be and what choices they should make.

Beneath that impulse is something even more uncomfortable and hard to reconcile: our tendency to judge is as much about us as it is about them. Because when we look at our kids, we see ourselves.

It was saying those last words that made me crack on stage.

As both a researcher and a parent, I’m overwhelmed by the scale of what we’re up against–empathetic AI colliding head-on with people’s deep need to feel seen, affirmed, and even praised.

Based on the trends and research I’m seeing, I’m deeply convinced that if rising generations (including my own daughters) feel too judged, or even just perceive too high a risk of potentially being judged, they will be lured in by sycophantic AI companions instead of turning to the people around them.

That risk feels especially acute in the era where social media has scaled the near-constant possibility of judgment—transforming what psychologists have long dubbed the “imaginary audience” (adolescents’ false sense that everybody is watching them) into an actual, 24/7 online audience. That digital reality is creating the perfect conditions for AI to offer a seemingly safe, judgement-free escape—for kids and adults alike.

If judgment hinders connection, AI widens that gap

One reason this is so worrisome is that turning to AI to avoid judgement doesn’t just create disconnection, it can compound it.

Stanford researchers found that sycophantic responses made users measurably more sure of themselves and their own opinions. And in the course of chatting with AI about an interpersonal conflict in their real lives, users became less likely to seek to repair those relationships.

Source: Sycophantic AI Decreases Prosocial Intentions and Promotes Dependence, 2025

In other words, “social sycophancy”—when an AI model affirms not just statements but the user’s own perspectives and self-image—carries particular risk. It doesn’t just make users feel good. It makes them less likely to engage in prosocial behavior with their family and friends.

More tolerance for each other… and for judgment itself

All of this suggests that we don’t just need to talk about AI, we need to talk about judgement, and how it hinders connection in the first place.

For adults, managing judgment is a tricky thing. Because we can only give others the grace we give ourselves. (I personally don’t give myself a ton of grace… and most moms I know feel the same). As I wrote about last week, I think some of the judgments adults tend to levy on kids’ relationship with technology reflect our fears about our own relationship to it, and the ways AI might harm our own well-being, distract us from our own development, or encroach on our own privacy.

So how do we curb the rush to judge young people… and maybe ourselves too?

Part of this is about summoning something that precedes judgment. According to my friend and colleague Stephanie Krauss, that’s curiosity. Talking to the young people in our lives about what they’re experiencing in an effort to learn and explore, rather than judge and teach, is a place to start. Luckily, the Rithm Project and Foundation for Social Connection have created a great starting point with a guide to intergenerational dialogue about AI.

Beyond curiosity, parents also need to strengthen our ability to see our kids in context. That comes from what’s called reflective functioning, i.e., understanding what’s behind children’s mental states to better understand, rather than judge, their behaviors.

But here’s the paradox that more curiosity and understanding towards our kids won’t solve: along with curbing our judgments towards kids, we also need to build kids’ tolerance for judgment. To withstand judgment, they need to know it’s part of living in the world, and hone their ability to dismiss it when it’s unfounded and to internalize it when it improves their understanding of themselves and the world around them. In fact, most research on social anxiety comes back to the fact that we can normalize judgment as part of the human experience so that it—and the mere possibility of it—wields less power over us.

In other words, parenting in the age of AI will require getting more attuned to how judgement shows up and how to shrink the distance it creates. Because it’s that distance that will drive young people toward AI and away from us.

To do that, our task is not to shield young people from judgment nor to jump to it. Instead, we need to lead with curiosity and understanding and to build relationships that can hold the rest. And maybe to find the grace to do that for ourselves too.