You Can Learn A Lot From A Bad Date

You Can Learn A Lot From A Bad Date

From Emily to Gremily by Emily Hogan

March 24, 2026 · 47 min

About this episode

Emily shares listener-submitted stories of disastrous first dates, highlighting the unpredictability of trust in dating.

A first date is basically a tiny audition for trust, and these stories prove how fast things can go off the rails. I’m coming to you on a mocktail (75 Hard is in the final countdown), then I open up a five-page doc of listener-submitted worst first dates that range from painfully awkward to genuinely scary. We get everything: a grocery store meet-cute that turns into a surprise showdown at the ex’s workplace, a dinner date interrupted by a mom who will not stop calling and FaceTiming, and a T...

Topics covered

  • dating
  • trust
  • awkward situations
  • listener stories

Keywords

  • first date
  • bad date
  • awkward
  • listener stories

Mentioned in this episode

Products: mocktail, 75 Hard

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