Jackie Shames, friend and co-host of Fill Your Cup is back to chat all things confidence, learning from past relationships, and staying true to who you are. Jackie shares her experiences dating between Miami and New York, how the seasons have been impacting her dating life, and the challenges of balancing personal and professional life. We discuss the the New York influencer scene, friendship dynamics, and podcasting, and we live-text someone Jackie went on a date with.

00:00 - 09:30 Navigating Confidence and Dating

09:30 - 26:24 Unexpected Encounters

26:24 - 28:54 Reflecting on Closure and Moving On

28:54 - 29:49 The Importance of Detachment

29:49 - 31:25 Running Into an Ex-Fling

31:25 - 33:24 Finding Security in a New Relationship

33:24 - 36:26 Navigating Dating Patterns and Self-Sabotage

36:26 - 43:38 Balancing Personalities in Relationships

43:38 - 55:53 Influencer Culture and Personal Growth

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