Second Date Update: First Date Redate

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

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. 

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. 

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. 

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. 

You won’t believe how the guy in today’s Second Date managed to score a date with a Perfect 10! He got the first date, but now he needs our help trying to wrangle another…See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date Update flew across the ocean just to meet someone he think MIGHT be the ONE. Find out what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date Update made a BOLD REQUEST before we even called his date. Was it fair? Sure! Was Brooke offended by it? Yep! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information. 

The guy in today’s Second Date is wondering if the surprise he prepared on the first date was TOO MUCH, and now wants our help to reconnect with the woman he might have scared away!See omnystudio.com/listener for privacy information. 

In today’s Second Date Update we had a listener caught in the most awkward position you could hope to be in on a first date. Find out what it was in the podcast!See omnystudio.com/listener for privacy information. 

The woman in today’s Second Date Update agreed to meet up with a man before she even knew his name, and it’s all because of one grand romantic gesture!See omnystudio.com/listener for privacy information. 

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. 

The woman in today’s Second Date Update is trying online dating for the first time after leaving a long term relationship. Her first try went so well she’s reaching out to us for help!See omnystudio.com/listener for privacy information.