WLW Lore: Caroline Calloway

Alix and Kayla dive deep into the wild, chaotic, endlessly fascinating lore of Caroline Calloway — from Instagram fame and ghostwritten captions to book-deal drama, retreat controversies, and the blurred lines between “scam,” self-mythology, and survival. The wives break down the friendship between Caroline and Natalie Beach, the homoerotic tension, the internet cancellation, the workshops, the snake-oil era, and why queer audiences are obsessed with this story.

If you love scammers, internet culture, WLW lore, or messy influencer history, this episode is for you.

00:00 – Intro: Reviews, comments & community love
01:30 – Who is Caroline Calloway?
01:50 – Scam or Stan game (NFTs, Erewhon smoothies, retreats, astrology apps)
04:50 – Breakup brands, viral masterclasses & influencer culture
10:00 – Why Caroline’s story is “entertaining, not dangerous”
11:00 – The WLW lore + homoerotic friendship dynamic
18:00 – How Caroline built her Cambridge-era Instagram persona
21:00 – Natalie ghostwrites captions & the early partnership
28:20 – The $500K book deal & $100K advance
30:30 – Addiction, missed deadlines & the fallout
34:20 – Whose side are you on?
35:20 – The infamous “workshops”
37:00 – Is it a scam if people willingly pay?
38:20 – The cancellations & venue chaos
42:30 – Snake oil, villain era & Caroline’s pivot
43:40 – “I Was Caroline Calloway” & Natalie’s takedown essay
48:40 – Natalie’s book deal + riding coattails
49:55 – Caroline’s tragic family news amid cancellation
53:45 – Obsession, shamelessness & survival mode
54:40 – New York era, OnlyFans, and rising again

#CarolineCalloway #ScamOrStan #InfluencerCulture #NatalieBeach #InternetDrama #Podcast #QueerPodcast #WLWLore #MessyInfluencers #BookDealDrama #CarlowayLore #OnlineScams #InternetHistory #WomenWhoWrite #CouplePodcast #AlixAndKayla

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