Second Date Update: The Long Game

FULL SHOW: Monday, September 14th, 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. 

We scoured the back pages of Craigslist to find the best (or is it worst?) entries from their Missed Connections section! Whether you're a hopeless romantic or just plain hopeless, this might be the place for you!See omnystudio.com/listener for privacy information. 

The woman in today’s Second Date was in shock once she ended up back at a guy’s place. There was no question she wants to see him again, but the real question is why doesn’t he want to see her?See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date is wondering if the surprise he prepared on the first date was TOO MUCH, and now wants our help to reconnect with the woman he might have scared away!See omnystudio.com/listener for privacy information. 

When the woman on the phone today described her job to us we were SHOCKED… but is it something that would keep her from a happy dating life? Find out in a brand new Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners invited her date back to her place and spent HOURS together… but what she saw him do… she’s STILL trying to process. Hear what she went through in a new Second Date Update!See omnystudio.com/listener for privacy information. 

Part 1 A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your Second Date Update. Part 2 The entire show was very surprised by how today’s Second Date finished. And we think all ou ... Show More

How long would you wait for a first date to show up before bailing? The listener in today’s Second Date waited 60 minutes for them to show their face and you’ll be shocked at what happened once she finally arrived!See omnystudio.com/listener for privacy information. 

The woman on the phone today says her date decided to switch booths HALFWAY through their dinner… And all of us were stunned when we finally learned the actual reason he demanded to move locations...Hear for yourself in a brand new Second Date Update!See omnystudio.com/listener f ... Show More

Part 1 One of our listeners said she met a guy the other night who almost got her ARRESTED. So why does she want another date with him?? Time to find out! Part 2 The woman on the phone says both she AND her date were asked to leave bar trivia over the most ridiculous reason, but ... Show More

One of our listeners had the SHOCK OF A LIFETIME after being set up on a blind date by her friend. As soon as she showed up she knew something was very wrong… Hear her story in the Second Date podcast!See omnystudio.com/listener for privacy information. 

It’s SHOCKING to learn where the listener on the phone met a new love interest today, and it’s even more shocking that he somehow swung that interaction into a date! Hear the where, why and how coming up in your Second Date Update!See omnystudio.com/listener for privacy informati ... Show More