When I tell you that this may be one of the most moving conversations on We Didn’t Turn Out Ok so far, I’m still not doing it justice.

Having Whitney Port on brought me back to growing up what felt like with her—from watching The Hills, where she seemed to live in an alternate world from my "Varsity Blues" suburbs in NJ to following her journey as she began filming for The City, where she carved her space in fashion and seemed to have everything fall into place. She met her now-husband Timmy (then a producer on the show), and began creating what she calls “beautiful things”—both professionally and personally.

But if you’ve followed along with Whitney’s story, you know she’s opened up bravely and publicly—about how things didn’t stay perfectly “in place.” About how pregnancy didn’t feel magical, how her experience of starting motherhood felt really sudden and how she’s now navigating an ongoing six-year fertility and surrogacy journey. Her honesty has been incredibly powerful for those who follow her, they feel connected, seen and supported in her sharing. I wondered what was left to uncover.

It turns out—so much more that we will all connect to— in different ways. 

In this conversation, Whitney shares the feeling when she sees another mom in a moment, how that can feel easy to judge until we then experience the same in her own parenting. She talks about how realized that it’s not about judging anyone else or ourselves, but about awareness and confidence in how we are showing up as a parent. She shares the emotional landscape that’s shaped her: from being one of five siblings in a home where it sometimes felt like her feelings often didn’t have space, to seeing a beautiful example of a marriage in her parents, to the boundaries that were set forth for her and her siblings, to learning what emotional safety really means—first for herself, and now for her son, Sonny.

This is a conversation about permission: to feel, to be unsure, to heal, and to show up—even when it feels like we don’t know exactly how. To be the kind of parent who’s still learning, still healing, still growing.

Spoiler: we both shed tears reflecting on how we were raised, and how that contributed to who we are today.

She’s amazing. This one’s special.

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