Second Date Update: Let's Chalk About It

Second Date Update: Let's Chalk About It

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Second Date Update: Shark Tanked

One of our listeners took his date to a ball game and INSTANTLY she was set off on a bad mood. He doesn’t know what sparked it but we’re on his side and we’re gonna dig in, when we do a Second Date Update!See omnystudio.com/listener for privacy information. 

FULL SHOW: Jeff’s World Cup Song, No Questions EVER Date + Dumbest Political Troll (6/12/26)

Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, June 12th, 2026 Curious if we look as bad as we sound? Follow us @Brooke ...  Show more

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Second Date Update: Mistah Secure
Brooke and Jeffrey

Typically on a first date, you’re supposed to do something fun and not invite someone to your work... But the guy in today’s Second Date did the second option and now he’s calling us for help fixing his love life!See omnystudio.com/listener for privacy information. 

Second Date Update Classic: Cake By The Tesla
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The guy from today’s Second Date brought his dinner date back to his place, but before the magic could begin.. something tragic happened!See omnystudio.com/listener for privacy information. 

Second Date Update: Hey Pineapple
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The guy in today’s Second Date has a strategy for giving a nickname on the FIRST DATE that he swears is undefeated. Hear what it is in the podcast!See omnystudio.com/listener for privacy information. 

He Disappears in Between Dates?
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Imagine this: You’re casually dating a guy you really like. He makes plans with you on a Monday for the following weekend, and says he’s looking forward to seeing you, and then… SILENCE. Tuesday, Wednesday, Thursday, Friday…no phone calls, no texts, nothing. What does this mea ...

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