In this Season 7 premiere, Auntie Kiki (Kiki Astor) shares a deeply personal story about returning from a vacation in France and realizing she dreaded going home to her own life. That devastating moment at the airport — wishing she could go anywhere except back — became the catalyst for a complete rethinking of what makes a life worth living. Drawing from her experience growing up wealthy and now living with less, Kiki argues that money doesn't automatically buy a life you love. Wealthy people, she observes, often spend astonishing amounts making their own lives unnecessarily difficult — enormous houses far from everything, second homes that become second jobs, boats that are more burden than pleasure.

The episode's central question: Do you actually want the life you keep paying to maintain? Kiki walks through how to distinguish genuine luxury from expensive inconvenience, how to audit the friction in your everyday life, and how to borrow the conditions that make vacation feel so alive — unhurried time, outdoor living, good food, real connection — and bring them home. She covers the fantasy of arrival, hedonic adaptation, the trap of living for an invisible audience, and why etiquette is really about managing friction. The episode ends with a practical "vacation life audit" to help listeners identify what they miss about vacation and bring those elements into ordinary life.

Awkward Etiquette: Old Money and New Manners Season 7, Episode 1 — "Craft a Life You Don't Need a Vacation From" Host: Kiki Astor

• The airport moment: when returning home feels worse than going anywhere else
• Why a beautiful house is not a beautiful life
• Money gives options, not automatically a life you love
• The enormous house problem: 17 bedrooms, 45 minutes from everything you enjoy
• Second homes as second jobs: packing, repairing, managing, coordinating
• Boats: the two happiest days are buying it and selling it
• Smart vacation homes: 45 minutes apart, not hours
• Three questions for any purchase: Will it improve my daily life? Will it reduce or create friction? Do I want the thing or the image?
• The Birkin bag debate: status symbol vs. actual utility
• Distinguishing what looks impressive from what feels good
• A rich life = less unnecessary friction + more intentional pleasure
• Vacation as information, not just reward
• The fantasy of arrival: "once I earn more, I can relax" — but the goalposts keep moving
• Hedonic adaptation: why the luxury car becomes just a car that needs new tires
• Living for an invisible audience that already made up its mind about you
• Micro frictions: the small annoyances that make daily life feel hostile
• Etiquette as the management of friction — not about forks
• Preparation as a form of elegance
• Boundaries as etiquette toward yourself
• Entertaining like you're on vacation: good olives, great bread, undivided attention
• The vacation life audit: identify your vacation fantasy, separate the feeling from the scenery, bring three things home
• Sensory practices to start tonight: wear the linen, drink the wine on a Tuesday, buy the flowers, play the music
• Rituals make ordinary days feel significant — without them, coffee is just caffeine and dinner is just calories

• Midnight Blue by Kiki Astor — available on Amazon (Kindle, paperback, audiobook)
• The Calamity Club — recommended read
• Service Entrance by Kiki Astor — referenced re: Santa Barbara's "June gloom"
• Villa for Rent by Kiki Astor — referenced re: St. Barts

"The real luxury is being able to come home from somewhere rather extraordinary and think, 'Oh, good, I'm home.'"

• Join the mailing list for weekly Monday emails and quizzes (Kiki boots you off if you don't open emails after a month or two)
• Awkward Etiquette: Old Money and New Manners podcast