What does it mean to love a place deeply and know when it’s time to leave?

New York Times bestselling author and Pulitzer Prize finalist Xochitl Gonzalez joins Jeana and Rachel for an expansive conversation about the places that make us, the people who remember our earlier selves, and the courage it takes to enter a new chapter.

Xochitl reflects on Brooklyn as both a hometown and a living archive. She also talks about writing Last Night in Brooklyn as one final love letter to the place that shaped her. She shares what decades-long friendships have taught her about grace, why closeness doesn’t always require constant contact, and how pre-digital friendship allowed people to become part of a community without feeling watched.

She also opens up about beginning her writing career in her 40s after years as a luxury wedding planner, the way class can narrow our sense of what’s possible, and why we should periodically reconsider our own “aperture of opportunity.” Plus, Xochitl talks manifestation, intergenerational mentorship, the connections she still hopes to make, and learning to trust that the road we started on isn’t necessarily the one we have to stay on.

Before the interview, Jeana and Rachel share moments when an improbable future felt inevitable. And in Show & Tell, they consider children’s autonomy online and whether we should ask permission before sharing photos of the people we love.

Media in this episode:

• Xochitl Gonzalez’s website
• Last Night in Brooklyn
• Olga Dies Dreaming
• Anita de Monte Laughs Last
• Need Blind: A Memoir of Class and Climbing in America
• Xochitl’s Substack
• Xochitl on Instagram

• Billy Joel: And So It Goes — the documentary that led Xochitl to a remarkable new connection.
• “Robby Hoffman Will Always Feel Poor, No Matter How Rich She Gets” — the New York Times interview Rachel references.

• Eventually Ticketing — use code CONNECT10 for 10% off the first year.