Brooke and Jeffrey: Second Date Update

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 omnys...

27 Nov 202518min

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 202517min

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 p...

25 Nov 202519min

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 omn...

24 Nov 202518min

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 feedba...

23 Nov 20251h 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 barist...

22 Nov 202537min

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 list...

21 Nov 202519min