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/list...
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/lis...
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 o...
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 inform...
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/listen...
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 feedba...
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 Upda...
10 Jan 37min
Second Date Update: Bathroom 911
The guy on the phone today is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation? Find out...
9 Jan 17min
