Hitting Rock Bottom (& Bouncing Back) with Sydney Kaplan

Hitting Rock Bottom (& Bouncing Back) with Sy...

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Red Flags or Dealbreakers? What We'd Think Now vs. When We Were Single

Happy Monday! We're recording from Jake's childhood bedroom fresh off a wedding the night before. We talk about why we're obsessed with vows and speeches, what it's like to hear other couples' love stories and reflect on your own relationship, and the text a maid of honor read al ...  Show more

My Dating Mistakes I Understand Differently Now

This solo episode is all about hindsight, growth, and the dating choices I understand differently now. I’m reacting to listener-submitted scenarios through two lenses: what past me probably would’ve done, and what I’d do now. We’re talking about emotionally unavailable people, co ...  Show more

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