Gen Z vs Classic Movies: Billy Madison

Part 1 One of our listeners isn’t sure if his date meant to VANISH or if there was just miscommunication but you can tell us what you think after you hear it. Part 2 Today we’re shaking it up and doing an ALTERNATE version of our Second Date Update… Going to levels we’ve never go ... Show More

FULL SHOW: Friday, August 28th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information. 

Have a knack for trivia? Well, so does Brooke… Try to answer as many questions right as you can in 30 seconds. If you answer more correctly than Brooke, you win 100 bucks! Good luck!See omnystudio.com/listener for privacy information. 

There’s a fine line between unbridled romance and complete humiliation and in today’s new Second Date we’re defining that line!See omnystudio.com/listener for privacy information. 

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

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. 

Part 1One of our listeners puts 2 little letters on her dating profile to let people know she’s into a VERY SPECIFIC type of thing… We're about to find out what those letters are and what they mean coming up.Part 2 The peculiar thing one of our listeners saw when he picked up his ... Show More

One of our listeners decided his goal was to bring the magic of RomComs to his dating life. You’ll find out how during an all new Second Date Update!See omnystudio.com/listener for privacy information. 

How can you parlay one night of fun with a person you met at the club into something more meaningful? We're going to help one of our listeners try to do exactly that in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for ... Show More

Our listener on the phone today says his date set a boundary before they even met in person. He had to say “yes,” to get a shot at her, and now we’re trying to get her to say “Yes” to a Second Date!See omnystudio.com/listener for privacy information. 

<p>Imagine being on a date and the server points out your BIGGEST insecurity&hellip; It happened to one of our listeners and you can hear what it was coming up in your Second Date Update podcast!</p> <p>Get your 2nd Date Update Merch For A Cause&nbsp;<a href="https://www.theshopf ... Show More

After one of our listeners met a man on a unique dating website she swears she CAN’T let him slip away! We’ll help her with a brand new Second Date podcast!See omnystudio.com/listener for privacy information. 

One of our listeners was DITCHED on a date in a BRAZEN way and so today we’re on the hunt for ANSWERS in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.