Awkward Tuesday Classic: Invisible Girlfriend
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 priva...
23 Dec 202516min
#6 Second Date Update of 2025: Lonely Cannoli
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 privac...
22 Dec 202517min
FULL SHOW: Dating App Hack Date, Brooke vs Christmas Dads + Jeff’s Back Alley Boat (12/17/25)
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...
21 Dec 20251h 5min
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! ...
20 Dec 202536min
#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 in...
19 Dec 202517min
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 Dec 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 Dec 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 Dec 202517min
