In this episode of Awkward Etiquette, host Kiki Astor—former Greenwich golden girl turned Montecito-adjacent observer—dives into the psychology, etiquette, and everyday acrobatics of living near the ultra-wealthy without actually being one of them. Whether you're sipping $7 cold brew in the shadow of a $70M estate or attending a fundraiser where your thrifted Loro Piana blazer is one dry-cleaning away from falling apart, this episode is for you. Inspired by her deliciously sharp new novel Service Entrance, Kiki dissects the invisible rules of old-money enclaves, from how to dress when you're underdressed to the emotional labor of blending in with billionaires. She explores luxury envy, stealth wealth, club culture, class-passing, and the psychological toll of being close—but not in—the club. With segments on status symbols, social survival, aspirational interiors, and what your car says about your net worth, this episode is essential listening for anyone who’s ever parked a sensible sedan beside a Bentley and felt... feelings, or if you've ever wondered why we envy, admire, love and hate rich people- and how to live alongside them when you don't have the same means. These are the life skills for non-billionaires who nevertheless live near them, in what might as well be a different world.

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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