Second Date Update Classic: Train Game
There’s no EASY way to approach an attractive person on public transportation, and that was exactly the case for our listener! She’ll tell us her story and how she wants to get in touch with a guy she...
22 Maj 17min
Awkward Thursday: 30 Day Girlfriend
Normally, we help people get second dates after a first one, but today we’re helping a guy who hasn’t even had ONE date with the woman he’s interested, and he wants to jump straight into a relationshi...
21 Maj 19min
Second Date Update: The Roadside King
One of our listeners says he DEFINITELY has someone to thank for his unforgettable date night. But the weird part is… that person isn’t exactly ALIVE… See omnystudio.com/listener for privacy informati...
20 Maj 17min
Awkward Tuesday: Something Smells In Canada
We’re dealing with an INTERNATIONAL ROMANCE EMERGENCY in today’s Awkward Tuesday Phone Call! We’re putting all our efforts behind getting one woman to FINALLY pick up the phone for her boyfriend…See o...
19 Maj 19min
Second Date Update: Mistaken Identity
Our listener on the phone today went out of his way to do the KIND, HONEST, and RESPECTFUL thing for his date… but it ended him up here with us and out of luck and love! Luckily, we can help him with ...
18 Maj 18min
FULL SHOW: Corpse Kiss Date, Jeff vs AI Song + Clover DoorDash Detective (5/13/26)
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: ...
17 Maj 1h 6min
Second Date Update Classics: I've Dated My Date Before + Two Word Whisperer
Part 1 One of our listeners had the SHOCK OF A LIFETIME after being set up on a blind date by her friend. As soon as she showed up she knew something was very wrong… Part 2 The woman on the phone toda...
16 Maj 36min
Second Date Update: Ramen Common
The woman on the phone today shared a SHOCKING secret in today’s Second Date Update. We were cool with it at first but by the end of the call our jaws were on the floor! See omnystudio.com/listener fo...
15 Maj 18min
