Yesterday

Second Date Update: Bachelor Party of One

This may be the BIGGEST RED FLAG we’ve ever heard on a first date… yet somehow, they still hooked up afterwords?? See omnystudio.com/listener for privacy information.

17m 42s

Jan 25

FULL SHOW: Jeff’s Plant Daddy Song, Bridal Bounty Date + Most Insane Reality Shows (1/23/26)

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 ... Show More

1h 4m

Jan 24

Second Date Update Classics: Beauty and the Meh + Getaway Car

Part 1 The guy on the phone today says he managed to pull a woman WAY out of his league, and it's all thanks to ONE move he pulled at the very end of the date! Part 2 One of our listeners says he doesn’t need help getting a hold of the woman he dated… he needs our help to avoid c ... Show More

37m 25s

Oct 4

Second Date Update Classics: Ex-Aversary + Lady In Red

Part 1 The guy from today’s Second Date Update said he got a text that completely BAFFLED HIM considering how good his first date went...You’ll hear about the weird message he received coming up. Part 2 An interaction on the dance floor led to one of the most embarrassing situati ... Show More

34m 34s

Jan 2025

Second Date Update: Ex-Aversary

The guy from today’s Second Date Update said he got a text that completely BAFFLED HIM… considering how good his first date went. You’ll hear about the weird message he received coming up in the podcast!See omnystudio.com/listener for privacy information.

16m 22s

Jul 2024

Second Date Update: Barwreck

Today’s Second Date Update includes probably the MOST AWKWARD 20 minutes of a first date we’ve ever had on this show. And it’s all because of an embarrassing run-in that happened at a bar!See omnystudio.com/listener for privacy information.

17m 25s

Jun 2025

Second Date Update Classics: 2nd Chance Scott + Mysterious Wallet Situation

Part 1 One of our listeners took a woman on a BEACH DATE and he gets huge props for one thing he DIDN’T DO… what was it? We're going to find out! Part 2 Today’s Second Date Update might involve one of the GREATEST SCAMS we’ve ever heard on a first date… Hear for yourself in the p ... Show More

37m 46s

Jul 2025

Second Date Update Classics: Secret Selfie + Day Date Surprise

Part 1 You won’t believe what one listener pulled off while on her date. Jose was FREAKING OUT that it was even possible! Hear for yourself in the Second Date Podcast! Part 2 The guy in today’s Second Date keeps ONE THING in his pocket to guarantee things go JUST RIGHT on every d ... Show More

37m 10s

Oct 2024

Second Date Update Classic: Love Me A Lengthy Lady

The guy on the phone today was asked an important question during his date, and in a moment of panic he thinks he may have given the most awkward response possible! Hear the Second Date podcast right here!See omnystudio.com/listener for privacy information.

16m 22s

Aug 2025

Second Date Update Classics: I Hope It's You + Fran-Fiction

Part 1 One of our listeners tells us she had an “intense moment” on her date, but it was a GOOD intense. So good, she’s desperate to get a Second Date Update with us! Part 2 The woman in today’s Second Date Update might have divulged a little TOO MUCH when she was asked about her ... Show More

37m 10s

Sep 2025

Second Date Update Classics: Twitchers Not Tweakers + Lobster Lunges

Part 1 Is it a green flag or a red flag when your date brings BINOCULARS on a first date? Our listener on the phone today said it’s a GREEN FLAG and he’ll tell us more about their magical experience coming up.Part 2 The guy in today’s Second Date Update knew a WEIRD amount of per ... Show More

37m 4s

Aug 2025

Second Date Update Classics: Pretty Fly for a Non- Brazilian Guy + Baddie and the Daddy

Part 1 The woman in today’s Second Date has to defend her one weird habit that she swears is NATURAL, but it left all of us shocked. Part 2 One of our listeners was brave enough to introduce his date to his FAMILY on night one! Hear all about this bold new strategy in your Second ... Show More

37m 54s

Oct 25

Second Date Update Classics: 10 Pin Mixup + Pop Goes the Relationship

Part 1How badly are you willing to embarrass yourself if it means getting a date with that special person? One of our listeners went to the limit LIVE ON AIR and you get to hear it!Part 2A listener on the phone today says his first kiss with his date left a LOT to be desired… and ... Show More

36m 4s

Second Date Update Classics: Ex-Aversary...