Second Date Update: First Timers Club
The guy on the phone today is a member of the “first timers club.” What’s the first timers club, exactly? Find out for yourself when we do a Second Date Update!See omnystudio.com/listener for privacy information.
21 Jan 19min
Awkward Tuesday: Don't Be A Negative Nanny
One of our listeners says the family she babysits for owes her a lot of money... And because they won't pay up, she's ready to confront them in an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.
20 Jan 18min
Second Date Update Classic: Pet Store Probation
One of our listeners has a unique technique in order to give herself a pick-me-up on a date. And not only did it work for her, it led her to a guy she really likes too! Hear her strategy in your Second Date Update!See omnystudio.com/listener for privacy information.
19 Jan 17min
FULL SHOW: Mom & Me Date, Brooke & Jeff’s Scam the Scammer Prank + Alexis' Granny Ghosts (1/14/26)
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, January 14th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.
18 Jan 1h 7min
Second Date Update Classics: Pop Some Tags + Love At First Flight
Part 1 A little drawing on a cocktail napkin didn’t go the way our listener planned, and neither did his date night! You’ll understand why in the Second Date Update. Part 2 Just when you thought nothing good happens on airplanes anymore, one of our listeners met a woman on a flight and his story might inspire everyone listening!See omnystudio.com/listener for privacy information.
17 Jan 36min
Second Date Update: Leave Wicky Alone
The guy on the phone today got caught showing up to his date after getting dropped off by ANOTHER WOMAN! We’re readying our battle stations for a contentious Second Date Update!See omnystudio.com/listener for privacy information.
16 Jan 18min
Second Date Update UPDATE: Pre-Block
One of our listeners asked his date a question that was RUDE, INSENSITIVE, and INAPPROPRIATE… at least we thought at first… Now he’s back for a special Second Date Update UPDATE!See omnystudio.com/listener for privacy information.
15 Jan 18min
Second Date Update: Mom Plus One
Ethan started his night meeting one woman, and ended up with a completely different one at his table by the end of the night! He’s desperate for a Second Date Update and we’re gonna give him one!See omnystudio.com/listener for privacy information.
14 Jan 17min
