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

Awkward Tuesday: Car Crash

Sep 15, 2026 · 18m

Summary

Listener Shelby calls in after accidentally hitting Joe’s car while distracted by his looks, seeking advice on how to ask him out. The hosts suggest bold approaches, including a "driving while gorgeous" pickup line, before Shelby calls Joe directly. The call goes hilariously wrong when Shelby mistakenly offers to babysit his kids, leading to a chaotic misunderstanding. Joe ultimately clarifies he is single and agrees to a date, turning the awkward incident into a romantic beginning.

Topics discussed

Ashanti Plummer and Geico sponsor segment Discover Cash Back Card promotion ChatGPT Work for productivity Granger shipping supplies ad CeraVe facial cleanser ad Hosts introduce Double Awkward Tuesday Listener story: Meeting a man via car accident CallX ad and listener intro Shelby explains the fender bender incident Shelby's dilemma: How to ask him out Hosts prepare advice for the call Awkward Tuesday Phone Call intro Brooke advises direct approach Jeff suggests a pickup line Shelby calls Joe and sets up a date Misunderstanding: Babysitting vs. Date Joe reveals he thought she was a babysitter Clarifying the 'DWG' joke and single status Wrap up and good luck to the couple Ashanti Plummer post-draft update CeraVe facial cleanser ad (repeat) Hosts discuss the car accident trend Call to action for listener updates Ashanti Plummer and Geico sponsor segment (repeat) ChatGPT for Business ad Zepbound weight management ad TD Bank human banking ad Granger cleaning supplies ad
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