The Real Reason Conversations Die on Dating Apps

The Real Reason Conversations Die on Dating Apps

From I Hate Dating Apps by Jinah Kim, Daniel Yi

January 27, 2026 · 45 min · Season 2 · Episode 41

About this episode

This episode features communications coach Rebecca Williams discussing effective conversation strategies for dating apps.

Everyone thinks they're a great communicator… until they open a dating app. 😅 If you've ever struggled to get a conversation off the ground with a total stranger—or found yourself stuck at a painful "hello"—this episode is for you. Daniel and Jinah sit down with Rebecca Williams, a professional communications coach who advises top CEOs and recently found herself back on the dating apps. ( https://rebecca-williams.com/#top) With both expert insight and real-world experience, Rebecca shares practical tips and mindset shifts to help you move past awkward openers and into actual connection. This episode covers dating app communication tips, messaging mistakes to avoid, how to stand out without overthinking, and what actually works when talking to strangers online. Whether you're new to dating apps or burned out by ghosting and stalled conversations, this episode will help you communicate with more confidence and clarity.

People in this episode

Hosts: Jinah Kim, Daniel Yi

Guest: Rebecca Williams

Topics covered

  • dating apps
  • communication
  • relationships
  • interpersonal skills
  • messaging tips

Keywords

  • dating apps
  • communication tips
  • awkward conversations
  • messaging mistakes
  • confidence

Mentioned in this episode

Organizations: rebecca-williams.com

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