Second Date Update: Lonely Cannoli

FULL SHOW: Monday, July 20th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

Have a knack for trivia? Well, so does Brooke… Try to answer as many questions right as you can in 30 seconds. If you answer more correctly than Brooke, you win 100 bucks! Good luck!See omnystudio.com/listener for privacy information. 

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a brand new Second Date Update!See omnystudio.com/listener for privacy information. 

Our listener on the phone today says his entire night was ruined when his date reached down and pulled something out from between the seats of his car... It was definitely incriminating and even left all of us in shock! Hear for yourself in a brand new Second Date Update.See omny ...  Show more

A little drawing on a cocktail napkin didn’t go the way one listener planned, and neither did his date! You’ll understand why in the Second Date Update podcast!

Get your 2nd Date Update Merch For A Cause <a href="https://www.theshopforward.com/collectio ...

One of our listeners claims she was just TRYING to flirt, but it went so badly it almost caused the guy to crash his car! Hear what happened in your Second Date podcast!See omnystudio.com/listener for privacy information.