
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 inform...
18 Des 202519min

#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 o...
17 Des 202517min

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 Awk...
16 Des 202517min

#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 202518min

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 feedba...
14 Des 20251h 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...
13 Des 202536min

#10 Second Date Update of 2025: Give Him The Golden
One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her, he had to do THIS first. Find out what it is in your Second Date Update podcast...
12 Des 202518min

Textual Healing: Dog Disturbance
One of our listeners is having a problem dealing with her next door neighbor and it’s slowly ruining her life. We’ll try to help her with some Textual Healing!See omnystudio.com/listener for privacy i...
11 Des 202518min





















