Yesterday

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

Yesterday

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

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 knew a WEIRD amount of personal i ... Show More

37m 4s

Jan 2025

Second Date Update: Twitchers Not Tweakers

Is it a green flag or a red flag when your date brings BINOCULARS on a first date? The listener on the phone today said it’s a GREEN FLAG and he’ll tell us more about their magical experience coming up in the Second Date Update podcast!!See omnystudio.com/listener for privacy inf ... Show More

17m 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

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

May 2025

Second Date Update: A Picture Says A Thousand Icks

Our listener on the phone today claims his date said one specific thing to their waiter that wasn't just a green flag...but made him instantly realize she was relationship material! You’ll hear what it was in your brand new Second Date Update! Get your 2nd Date Update Merch For A ... Show More

18m 5s

May 2025

Second Date Update Classics: Picture Says It All + Promotion Commotion

Part 1: One of our listeners figured out a way to get his entire evening PAID FOR, and it involved no lying, not scheming and not cheating. How did it work? We're going to find out! Part 2: One of our listeners says it was a HUGE PLUS that his date listened to our show! That shou ... Show More

34m 8s

Sep 2024

Second Date Update: A Picture Says It All

One of our listeners says it was a HUGE PLUS that his date listened to our show! That should have been his first red flag, now he wants our help in a brand new Second Date podcast!See omnystudio.com/listener for privacy information.

17m 19s

Mar 2025

Second Date Update: First Date Redate

Get your 2nd Date Update Merch For A Cause HERE! The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE!See omnystudio.com/listener for privacy information.

17m 34s

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

Second Date Update Classics: Twitchers N...