Second Date Update: Beauty and the Meh

FULL SHOW: Monday, August 25th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee 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. 

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. 

Destiny took over at a Bachelorette Party, and the guy it ensnared has actually been on our show before! Fate is coming one way or another in a brand new Second Date Update!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. 

One of our listeners decided his goal was to bring the magic of RomComs to his dating life. You’ll find out how during an all new Second Date Update!See omnystudio.com/listener for privacy information. 

One of our listeners is on the line to tell us about the SURPRISE LOCATION he brought a woman to to try and win her over. Hear where it was in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners isn’t sure if his date MEANT to VANISH or if there was just miscommunication but you can tell us what you think after a new Second Date Update podcast!See omnystudio.com/listener for privacy information. 

Part 1 This might be one of the first International Second Dates we’ve ever done! So come take a ride with us in an ultra-classy Second Date podcast. Part 2 A fun activity to go along with dinner is normally a great date... NOT TODAY. The guy on the phone botched his night and no ... Show More

The guy in today’s Second Date Update flew across the ocean just to meet someone he think MIGHT be the ONE. Find out what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

One of our listeners took a PLANE FLIGHT to hang out with a woman he met online… but their date left a lot to be desired… We’ll try to fix their future in your Second Date Update podcast!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

One of our listeners has a perfect little trick to learn EXACTLY what a guy is thinking at the end of a date. Find out how she does it coming up in a brand new Second Date podcast!See omnystudio.com/listener for privacy information.