Second Date Update: Lonely Cannoli

Part 1 One of our listeners says a DEAFENING silence happened after an awkward question from their waiter on their date, and now she’s not getting a call back. Part 2 The woman on the phone today claims that she discovered a place that is swarming with career driven, high-value m ... Show More

We're pitting the generations against each other with the ultimate trivia game, it's Brooke vs. Alexis!See omnystudio.com/listener for privacy information. 

FULL SHOW: Friday, July 17th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee 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

<p>A little drawing on a cocktail napkin didn&rsquo;t go the way one listener planned, and neither did his date! You&rsquo;ll understand why in the Second Date Update podcast!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a href="https://www.theshopforward.com/collectio ... Show More

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. 

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night! Hear what happened in a new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy in ... Show More

One of our listeners DEFINITELY regrets a story he told on his date, and you’re gonna want to hear how he tells it in the Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners says his plan to impress his date and make her like him did NOT go how he wanted… in fact his night ended in physical pain! Hear it all in your Second Date Update!See omnystudio.com/listener for privacy information. 

Our listener on the phone today says 5 min into his date he realized he forgot something MAJORLY important. Hear what slipped his mind and how we’re helping him gain back ground in a new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners THOUGHT he had a second chance all lined up with his date, but a single one-word text message brought that reality crashing down. Hear what it was coming up in a new Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners had a GREAT first encounter with his date, but it was his FIRST TEXT after it ended that wrecked things… Hear what he sent coming up in your Second Date Update!See omnystudio.com/listener for privacy information.