Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall

One of our listeners planned a first date to last 5 full days with a woman he had never even met before! We’ll hear what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

24 Des 16min

In your Awkward Tuesday Phone Call, one of our listeners is convinced her brother is hiding a big secret from the family, and she wants to reveal it with our help!See omnystudio.com/listener for privacy information.

23 Des 16min

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 Second Date Update!See omnystudio.com/listener for privacy information.

22 Des 17min

We're trying out a new idea for our fans of the 2nd Date Update! Every Sunday, we will be hosting 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: Wednesday, December 17th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

21 Des 1h 5min

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

19 Des 17min

It’s one of the most controversial segments in the history of our show, but today it comes with a twist. It's the Holiday Edition of Brooke Breaks You Up!See omnystudio.com/listener for privacy information.

18 Des 19min

The most annoying part of dating apps is all the wasted energy you put in, only to never actually meet up in person… But our listener on the phone says he has a method to eliminate that headache!See omnystudio.com/listener for privacy information.

17 Des 17min