Second Date Update UPDATE Classic: 8 Trees A Trimming
The holidays nearly broke up the couple on the phone today when they first dated a year ago. But now with the yuletide season coming up were going to reconnect with them for a special update!See omnystudio.com/listener for privacy information.
27 Nov 18min
Second Date Update Classic: First Date Redate
The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information.
26 Nov 17min
Awkward Tuesday: Stop That Ugly Duckling
Is it ever okay for a person to meddle in their friends love life? It doesn’t matter because we’re doing it anyway before one listener's friend can go on a blind date!See omnystudio.com/listener for privacy information.
25 Nov 19min
Second Date Update Classic: Red Flaggy Much?
One of our listeners said he made a restaurant faux pas RIGHT AWAY on his date before he even put down the menu. We’ll talk to him and see if it derailed his chances in your Second Date Update!See omnystudio.com/listener for privacy information.
24 Nov 18min
FULL SHOW: Jeff’s Iconic Thanksgiving Song, Turkey Day Mishaps + Late & Petty Date (11/21/25)
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: Friday, November 21st, 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.
23 Nov 1h 5min
Second Date Update Classics: Date Night Detour + Barista Foam Job
Part 1 If you asked a million people if they thought the surprise one of our listeners had for the woman he was dating was a good idea, NOBODY would say “YES!” Part 2 One of our listeners is a barista and says she did something she would NEVER normally do… but taking that risk got her a date with a hot customer and now she wants our assistance bringing him back one more time!See omnystudio.com/listener for privacy information.
22 Nov 37min
Second Date Update: Microwave Mosaics
Kevin’s unique hobby might be one of the weirdest things we’ve heard and we’re wondering if MAYBE it's reason he isn’t getting a call back...But it's also what makes him one of the most memorable listeners we've ever had on the show!See omnystudio.com/listener for privacy information.
21 Nov 19min
Top 10 Loser Lines of 2025
We're counting down our TEN FAVORITE Loser Line Clips of the entire year!See omnystudio.com/listener for privacy information.
20 Nov 18min
