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

Second Date Update Classics: Hotel Bar Rendezvous + Facebook KO

Oct 10, 2026 · 36m

Summary

In this episode, Brooke and Jeffrey discuss two "Second Date Update" stories. First, they call Delilah, who found Jack's coffee date boring, but she agrees to a second date after hearing about his quirky habits. Next, they reach out to Jessica, who rejects Danny after learning he physically confronts Facebook trolls in parking lots, resulting in a definitive rejection.

Topics discussed

Sponsorships: CVS Pharmacy and Grainger Prank call bot compilation and producer humor Listener Jack's first date at a hotel coffee bar Jack meets Delilah and the name mix-up Date details: appearance, conversation, and coupons Hosts' banter and transition to calling Delilah Phone call with Delilah: feedback on the date Delilah agrees to a second date Sponsors and post-call commentary on Jack Listener Danny's story: meeting Jessica at Whole Foods Hosts analyze Danny's date and prepare to call Phone call with Jessica: the 'Facebook Troll' misunderstanding Jessica rejects Danny; hosts discuss the hobby Sponsorships: CA, Rhapsido, and Lincoln
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