Second Date Update Classic: Guinness Wha...

Part 1 5 minutes into his date with Delilah, Jack realized he forgot something MAJORLY important. Hear what slipped his mind and how we’re helping him gain back ground! Part 2 The listener in today’s Second Date Update says that if we can’t help him, it’ll be the first time EVER ... 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, October 9th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

The guy in Today's Second Date attempted to become world-renowned for feet stuff. But, not only did he fail that venture, he failed to keep his date interested as well!See omnystudio.com/listener for privacy information. 

One of our listeners has one of the COOLEST claims to fame ever. But he’s worried its attracting the wrong type of woman… hear what it is in the Second Date Update podcast!See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date tried to come up with a cool date idea, and he did. But once they were there he had to CONSTANTLY say “NO” to his date. Can we help get a “yes” back from her?See omnystudio.com/listener for privacy information. 

<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 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. 

Part 1 The guy in today’s Second Date is a PROUD single-dad, but he thinks it also might be the reason for the downfall of his first date. You’ll hear what happened in the podcast! Part 2 One of our listeners has a perfect little trick to learn EXACTLY what a guy is thinking at t ... Show More

One of our listener's romantic gesture was NOT as well-received as he thought it would be. Was it too much? Let us know after you hear the Second Date 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! See omnystudio.com/listener for privacy information. 

Part 1 The guy in today’s Second Date Update tried a pickup line that was cringey, not just on one level… but on MULTIPLE LEVELS and he quickly realized he needed our help. Part 2 One of our listeners found themselves in the middle of an epic house party and he thinks he found a ... Show More

The guy in today’s Second Date took one classic date idea and flipped it on its head, making all of us in studio jealous when we heard it. Who is this beloved mystery man?See omnystudio.com/listener for privacy information.