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
Awkward Tuesday: Nerf Knights Forever
99.9% of boyfriends would NEVER ask their girlfriends what the guy on the phone today asked his. Now he wants our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.
13 Jan 20min
Second Date Update: Dry Lips & Hands On Hips
All the guy on the phone today had to do to make himself PERFECT for his date is change TWO PHYSICAL things about himself… It backfired and now he wants a Second Date Update! See omnystudio.com/listener for privacy information.
12 Jan 18min
FULL SHOW: Jeff’s Useless Resolutions Song, Bathroom 911 Date & The Craziest New Tech (1/9/26)
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: Friday, January 9th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.
11 Jan 1h 4min
Second Date Update Classics: Cobra Bye + Taco Truckstop Mystery
Part 1 One of our listeners didn’t admit her guilty pleasure to her date, she THEMED their entire evening around it. Now she’s not getting a call back? Part 2 One of the most popular Second Date Updates from last year is BACK… the bad news is the guy she went out with is trying to avoid her (he even RAN AWAY). We’re gonna try to find out why in the podcast!See omnystudio.com/listener for privacy information.
10 Jan 37min
