Rachel Bilson: From 2000s Nostalgia To Her Mom Era

Jan 20, 2026

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This week, I’m sitting down with one of my favorites, Rachel Bilson, for a fun, honest, girl chat. From growing up in L.A. and sneaking into Hollywood clubs as a teenager to getting into trouble, Rachel shares how she somehow managed to stay grounded through it all. She talks about getting the partying out of her system early — long before the job that turned her into an early-2000s icon.

We dive into that whole era of fame, including the harder parts: the public relationships, the headlines, and how they’ve made her censor herself today. Rachel opens up about dating now and what she’s genuinely looking for — including whether marriage or more kids are still on the table.

We break down co-parenting, her relationship patterns, and the surprising peace that comes from being completely content on your own. Rachel also shares the mindset she wishes she’d had in her 20s (and what she hopes younger women hear today).

Plus, Rachel on Broadway, Dancing With the Stars, and the mom conversations we all have: wanting our kids to actually come to us in high school, and why she’s holding off on giving her daughter a phone for as long as possible.

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Produced by Dear Media.

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