What happens when marrying for love wasn’t the point, but marrying for money definitely was? In this episode, Kaylee dives into the fascinating (and sometimes scandalous) history of “Dollar Princesses” — the wealthy American women of the Gilded Age who crossed the Atlantic to trade fortunes for aristocratic titles. Think Downton Abbey meets Succession, with a dash of modern side-eye.

Kaylee unpacks the cultural drama behind these transatlantic marriages: who benefitted, who got swindled, and how this age-old tradition of money-for-status still echoes in today’s relationships, celebrity pairings, and influencer “soft launches.” And of course, she spices it up with her own brand of wit, pettiness, and unapologetic hot takes.

If you’ve ever wondered whether romance can survive when the checkbook enters the chat, this one’s for you.

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