What happens when someone who isn’t a “match” on paper becomes one of your most important people—and stays that way?

I sit down with Sarah Orr, my daughter Emma’s former outdoor school teacher, our family’s nanny, coworker and creative collaborator for over a decade, and in a few months, a mother herself. Sarah came into my life when she was 23 and I was almost 40, and for the last thirteen years she has quietly witnessed every season of my adult life—including my journey into motherhood—and now I get to witness hers.

We talk about the Venn diagram of friendship that gets chunkier every year, what frozen pizza has to do with friendship resilience, and the moment Sarah found her late father’s painting in a thrift store—a bird on a cliff—on the same day a healer had described that exact image in her energy field.

We also get into cross‑generational friendship chemistry, “pebbling” as a love language, and what it actually looks like to build chosen family when nothing about it makes sense.

This isn’t about friendships that were meant to be. It’s about the ones that find a way anyway.

This episode is for anyone navigating a cross‑generational friendship, craving chosen family, or wondering if inviting a friend deeper into your life is the right move.

Sarah’s Friend Pick: The Infinity Pillow — the circular travel pillow she sleeps with everywhere.

Follow your new friend Sarah on Instagram: @sarah.from.maine

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