Brooke and Jeffrey: Second Date Update Brooke and Jeffrey: Second Date Update

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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