Second Date Update Classic: Burned By Beauties
Oct 9, 2026 · 18m
Summary
Listener Riley shares his awkward first date with Dana, which began at an animal mask art event, but he is now being ghosted after reaching out to her ex for background checks. The hosts call Dana to confront the situation, revealing that Riley has since become close friends with her ex. In a surprising twist, Dana rejects Riley but agrees to give her ex another chance, leaving Riley as the unexpected matchmaker.
Topics discussed
Sponsorships: OrderlyMeds and Discover Card
Listener messages and studio banter
Introduction to the Second Date Update segment
Riley's story: meeting Dana at an art installation
Riley's skepticism about beautiful women and the first date
Preparation to call Dana
Calling Dana: initial reaction and context
The revelation: Riley contacted Dana's ex
Riley and Dana discuss the ex and new friendship
Dana's decision and unexpected matchmaking
Post-segment wrap-up and sponsorships
Sponsorship: ZepBound for sleep apnea
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