Second Date Update Classic: Uptight Greg

One of our listeners is CERTAIN that the universe was talking to her when she met her DREAM MAN. The only problem? They kind met during a disaster and now she wants our help cleaning up after it! It's your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy informa ... Show More

The woman in today’s Second Date Update knows she didn’t give strong signals to the guy she’s interested. In fact, she stayed FAR AWAY from him the whole night! We’ll dig into why in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

Every Sunday, we host 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: Thursday, September 10th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJ ... Show More

One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!See omnystudio.com/listener for privacy information. 

<p>Imagine being on a date and the server points out your BIGGEST insecurity&hellip; It happened to one of our listeners and you can hear what it was coming up in your Second Date Update podcast!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a href="https://www.theshopf ... 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!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. 

The listener on the phone today wasn’t afraid to show off his sensitive side on his date, but the way he did it sent up some red flags in studio! Hear what happened in your Second Date podcast!See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date Update accidentally blurted out something so DUMB, it might have become the cringiest moment of his life. Relive his embarrassing moment right now in the podcast!See omnystudio.com/listener for privacy information. 

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. 

The guy on the phone today probably couldn’t have picked a more embarrassing way to end his date even if he tried! See omnystudio.com/listener for privacy information. 

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not calling back!See omnystudio.com/listener for privacy information. 

One of our listeners said he did EVERY FORM of communication he possibly could leading up to his first date…. And something STILL went wrong…. See omnystudio.com/listener for privacy information.