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Ever witnessed a train wreck you couldn't look away from? That's exactly what you'll get with Producer Ryan's bachelor auction story—a hilariously cringeworthy dating disaster that makes for podcast gold. When Ryan's friend (who previously friend-zoned him) convinces him to participate in a charity bachelor auction, things quickly spiral into comedy territory. From his ill-advised spin move prompting an audible "Oh geez" from the crowd to ultimately selling for just $30—the lowest bid of the night—Ryan's self-deprecating retelling had us in stitches.

But wait, there's more! The plot thickens when Ryan discovers his $30 bidder actually purchased multiple bachelors that night, explaining she was trying to drive up prices for charity. "It worked for everybody except you," she told him. The dating saga continues as Ryan later connects with a woman carrying a mysterious backpack on their first date—a "rosé flag" as he cleverly terms it, admitting his weakness for "a little bit of the crazy."

The episode shifts into a series of entertaining segments including "Would You Rather" dating edition (would you rather have a first date at Chuck E. Cheese or during a family reunion?), "Boo or Cool" fashion trends with Dave Ramsey, and "Red Flag or Go" dating advice from Paul from Beaumont. We wrap things up with an "Am I the Jerk" court case about a roommate dispute involving donated belongings. From start to finish, this episode delivers relatable dating horror stories, friendship banter, and genuine laughs that'll have you feeling better about your own romantic misadventures. Ready to feel better about your dating life? Hit play and subscribe now!