



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!

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!

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!

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!

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!

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 Curiou…

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…

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 in the Second Date Update!

Awkward Thursday: Long Distance Liar
One of our listeners hopes things aren’t falling apart with his long-distance girlfriend. And with our help he wants to make an Awkward THURSDAY Phone Call!

Second Date Update Classic: Eyes Closed Mouth Open
There’s one moment in every date where you can end on a high note, or push your luck and risk it all. One of our listeners says he definitely made the WRONG choice on his date and now he’s on the line looking for help with a Second Date Update.