Today

Shock Collar Question of the Day (8/26/25)

It's a special GIRL POWER edition of Plenty of Twenty!See omnystudio.com/listener for privacy information.

8m 35s

Yesterday

FULL SHOW: Revenge Date, Ex at the Wedding Loser Line + Paddle Daddy Prank (8/25/25)

FULL SHOW: Monday, August 25th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

1h 4m

Yesterday

Missed Connections (8/25/25)

We scoured the back pages of Craigslist to find the best (or is it worst?) entries from their Missed Connections section! Whether you're a hopeless romantic or just plain hopeless, this might be the place for you!See omnystudio.com/listener for privacy information.

7m 21s

Jul 5

Second Date Update Classics: Fast Service Disservice + Give A Hero A Chance

Part 1 One of our listeners had a very awkward and puzzling fact about himself get exposed on the show, but is it an instant deal breaker? Part 2 The guy on the phone today might have set the world-record for “Quickest Time To Ruin A Date” and he did it in under a minute!See omny ... Show More

37m 1s

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

Jul 26

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

Jun 7

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 19

Second Date Update Classics: Childlike Wonder What Happened + Silent Dancer

Part 1 The guy in today’s Second Date is a PROUD single-dad, but he thinks it also might be the reason for the downfall of his first date. You’ll hear what happened in the podcast! Part 2 One of our listeners has a perfect little trick to learn EXACTLY what a guy is thinking at t ... Show More

36m 27s

Jun 28

Second Date Update Classics: Hoping For A Bad Date + Nathan Of The Night

Part 1 A beautiful woman asked one of our listeners to take her out on a date… to a place she HATES! Why would she want that? We’ll get her to come clean in your Second Date Update. Part 2 The entire show was very surprised by how today’s Second Date finished. And we think all ou ... Show More

36m 27s

Nov 2024

Second Date Update: Brews and Bikes

The guy in today’s Second Date Update accidentally blurted out something so DUMB, it might have become the cringiest moment of his life. Relive his embarrassing moment right now in the podcast!See omnystudio.com/listener for privacy information.

18m 8s

Aug 2

Second Date Update Classics: Private Jet Regret + Hair Today Gone Tomorrow

Part 1 This might be one of the first International Second Dates we’ve ever done! So come take a ride with us in an ultra-classy Second Date podcast. Part 2 A fun activity to go along with dinner is normally a great date... NOT TODAY. The guy on the phone botched his night and no ... Show More

36m 35s

Jan 2025

Second Date Update: Plane In The Neck

We might have had one the most awkward “jump to conclusion” moments we’ve ever had on this show and we’re just shocked we didn’t screw it up for the guy. Hear it in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

18m 7s

Jun 16

Second Date Update: Doodle Worthy

One of our listeners tried a UNIQUE STRATEGY to extend his date.… and even he admits, it was WAY more cringe than he thought it would be… You’ll hear what happened in your brand new 2nd date update podcast!See omnystudio.com/listener for privacy information.

18m 50s

Second Date Update Classics: Fast Servic...