Brooke and Jeffrey Brooke and Jeffrey

Second Date Update: The Set Up

Nov 2, 2026 · 18m

Summary

Listener Megan calls in to apologize for a disastrous first date where she showed up late, spilled wine and pasta on her date Richard, and ordered excessive food. The hosts contact Richard, who is initially sympathetic, but the situation escalates when it is revealed Megan orchestrated the disaster as revenge for Richard ghosting her sister. The episode concludes with the hosts expressing shock at the calculated nature of the prank and the mutual toxicity of the parties involved.

Topics discussed

Intro: Daylight saving time and Halloween recap Megan's story: The disastrous first date with Richard Details: Getting wasted and showing up late The incident: Spilling wine and pasta on Richard Aftermath: Richard pays the bill and leaves Recap of mistakes and plan to call Richard Calling Richard: His initial reaction to the date Richard's perspective: Why he doesn't want drama The twist: Megan reveals it was revenge for her sister Confrontation: Richard admits to ghosting the sister Resolution: Both parties refuse to meet again Outro: Reflections on dating and revenge
Listen ad-free on Castria