Jan 17

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 flig ... Show More

36m 36s

Jan 17

Today vs Back in the Day (1/17/26)

We're pitting the generations against each other with the ultimate trivia game, it's Brooke vs. Alexis!See omnystudio.com/listener for privacy information.

14m 58s

Jan 16

FULL SHOW: Jeff’s Stuck in Traffic Song, Wittle Wicky Date + Only in the 90s Trends (1/16/26)

FULL SHOW: Friday, January 16th, 2026 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

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

Nov 2024

Second Date Update: I Hope It's You

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!See omnystudio.com/listener for privacy information.

17m 54s

Sep 2025

Second Date Update Classics: Rome-ANTS Isn't Dead + Standup Standoff

Part 1 The woman in today’s Second Date is for sure one of the most unique and interesting women we’ve ever had on the show...Buckle up. Part 2 We had a problem with today’s Second Date Update that we’ve NEVER experienced before and it probably says a lot about why one of our lis ... Show More

37m 55s

Jun 2025

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

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: Vacation No No

One of our listeners planned a first date to last 5 full days with a woman he had never even met before! We’ll hear what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

17m 4s

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 1

Second Date Update: There's A Chili In The Air

One of our listeners said probably the #1 thing you should NEVER EVER say on a first date… No wonder he needs our help, but we’re ready in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

18m 21s

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

Sep 2025

Second Date Update Classics: Italian Surprise + Mid Hookup

Part 1 One of our listeners said she met a guy the other night who almost got her ARRESTED. So why does she want another date with him?? Time to find out! Part 2 The woman on the phone says both she AND her date were asked to leave bar trivia over the most ridiculous reason, but ... Show More

36m 38s

Second Date Update Classics: I Hope It's...