Second Date Update: Let's Chalk About It

Second Date Update: Let's Chalk About It

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Second Date Update: Bachelor Party of One

This may be the BIGGEST RED FLAG we’ve ever heard on a first date… yet somehow, they still hooked up afterwords?? See omnystudio.com/listener for privacy information. 

FULL SHOW: Jeff’s Plant Daddy Song, Bridal Bounty Date + Most Insane Reality Shows (1/23/26)

We're trying out a new idea for our fans of the 2nd Date Update! 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, January ...  Show more

Recommended Episodes

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 PODCAST: Restaurant Singer
Brooke and Jeffrey

Today, one of our listeners emailed us... and when we got him on the phone we REALIZED that he was actually one of the nicest guys we've ever spoken to... Unfortunately, when it comes to dating... sometimes, nice guys do really DUMB THINGS... Good thing Jubal isn't a nice guy... ...  Show more

Second Date Update Classic: Cake By The Tesla
Brooke and Jeffrey

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
Brooke and Jeffrey

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.