Second Date Update Classics: The Boy Who Cried Tree + Deck The Mall
Part 1 After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time! Part 2 Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Second Date!See omnystudio.com/listener for privacy information.
20 Des 36min
#7 Second Date Update of 2025: Street Walker Love Story
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
Brooke Breaks You Up: Holiday Edition
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
#8 Second Date Update of 2025: That Name Sounds Familiar
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
Awkward Tuesday: Baby Monitor Drama
What if a family member overhears something they weren't supposed to, and now the holidays are going to be EXTRA WEIRD unless you make a phone call with our help? It's happening right here in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.
16 Des 17min
#9 Second Date Update of 2025: Dragon Thumbs & Aroma Chums
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.
15 Des 18min
FULL SHOW: Holiday Men Hack Date, Jose’s Midnight Meet Up + Smaller is Better for Jeff (12/10/25)
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 10th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.
14 Des 1h 7min
Second Date Update Classics: 3rd Times a Yawn + Super Kid Shames the Day
Part 1 The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before! Part 2 The guy on the phone says a random child walked up to their table during a romantic dinner and said something that threw off their ENTIRE EVENING. Is a kid really to blame for him not getting a Second Date?See omnystudio.com/listener for privacy information.
13 Des 36min
