Brooke and Jeffrey: Second Date Update

After many failed romantic encounters...and a couple of outright scams...one of our most lovable listeners is back! He says this time is different because he finally executed the perfect date night, at least for a few minutes. We'll find out what went wrong this time in your brand new 2nd Date Update!See omnystudio.com/listener for privacy information.

Published: 18 July 2025

A couple that met at holiday work party did a 2nd date with us way back in December. And after the call, we thought there was NO WAY this relationship would work out....but they are back with a very SURPRISING update about what's happened since being on the show!See omnystudio.com/listener for privacy information.

Transcribed - Published: 17 July 2025

One man was stuck in the friend zone for 20 YEARS until he got a call that changed his life...You’re gonna hear what he did on the date he waited two decades for in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 16 July 2025

One of our listeners is freaking out over what his new stepmom just posted online...He says it has potential to ruin their entire family dynamic UNLESS he can convince her to take it down. That's why he's come to us for help in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 July 2025

In today’s Second Date Update there was one moment that brought the evening to a SCREECHING HALT! Hear what it was in the podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 14 July 2025

Part 1 One of our listeners decided his goal was to bring the magic of RomComs to his dating life...Now we need to help him finish his love story! Part 2 The guy on the phone says one text before the date started changed their ENTIRE NIGHT—Find out what it was in your Second Date Update. See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 July 2025

When the woman on the phone today described her job to us we were SHOCKED… but is it something that would keep her from a happy dating life? Find out in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 11 July 2025

For the past few months we’ve been doing our own knock-off version of Netflix’s “Love Is Blind” but today there was a twist that even the contestants never saw coming!See omnystudio.com/listener for privacy information.

Transcribed - Published: 10 July 2025

One of our listeners claims they’ve discovered the GOLDEN pick-up line, hear what it is in a brand new Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 9 July 2025

After something went awry at a kid’s birthday party ONE YEAR AGO something is STILL causing a rift… and we’re being asked to settle it with a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 8 July 2025

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.

Transcribed - Published: 7 July 2025

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 omnystudio.com/listener for privacy information.

Transcribed - Published: 5 July 2025

Little mistakes are okay on a first date, but today's Second Date had one BIG mistake and we're hoping it didn't happen on purpose...See omnystudio.com/listener for privacy information.

Transcribed - Published: 4 July 2025

One of our listeners is having a CODE 9 emergency, which is why she stole her roommate's phone, and is now sitting in her car outside her apartment WAITING for us to help with some Textual Healing!See omnystudio.com/listener for privacy information.

Transcribed - Published: 3 July 2025

Is there a way to BETRAY a friend… but POLITELY? One of our listeners wants to do that, but she has a good reason for it and wants our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 1 July 2025

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 our listeners will agree… it was Brooke’s fault.See omnystudio.com/listener for privacy information.

Transcribed - Published: 28 June 2025

This segment might be one of our most difficult tasks we’ve faced this entire year! It’s an all new “SAY YES TO THE EX” and boy, is our work cut out for us!See omnystudio.com/listener for privacy information.

Transcribed - Published: 26 June 2025

One of our listeners warned her date that there’s ONE THING he HAD to do before she would see him… and he was shocked to find out she was SERIOUS. Hear what it was in a new Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 25 June 2025

One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 24 June 2025

One of our listeners is worried her gratitude for a gift was BADLY misinterpreted as rude and now she wants our help with a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 23 June 2025

Part 1 One of our listeners described their dinner date as the most IMPRESSIVE thing that they had ever seen. We HAD to know more so we contacted them as part of today Second Date Update. Part 2 One of our listeners admits he struggled to keep his cool on his date once he saw something on her Instagram. We couldn't believe it when we heard it either!See omnystudio.com/listener for privacy information.

Transcribed - Published: 21 June 2025

One of our listeners DEFINITELY regrets a story he told on his date, and you’re gonna want to hear how he tells it in the Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 20 June 2025

If you had to choose, would you pick your family or a life-changing amount of money? A listener was faced with that choice and today he’s discussing his decision on our show in a Closure Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 19 June 2025

The kiss that happened at the end of our listener's date was either the cutest, most spontaneous thing ever, or the cringiest, most awkward interaction of all time. Decide for yourself after the new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 18 June 2025

For one of our listeners, there’s ONE MAJOR THING standing in the way of the perfect graduation party for her son… and that’s her neighbor.See omnystudio.com/listener for privacy information.

Transcribed - Published: 17 June 2025

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.

Transcribed - Published: 16 June 2025

We've got a special new episode you this weekend! We’ve got two hopeful singles, ready to meet for the FIRST TIME on our show… and Brooke’s glasses are already on PRE-FOG…. In anticipation of BLIND LOVE IS!See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 June 2025

Part 1 Brooke has seen a lot in her 400 years in radio, but today one of our listeners put her in the most DRAMATIC and UNCOMFORTABLE situation of her entire career. Part 2 There’s some topics you just don’t bring up on a first date. One of our listeners didn’t follow that rule and now it’s no surprise he needs our help in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 14 June 2025

The woman on the phone today says her date decided to switch booths HALFWAY through their dinner… And all of us were stunned when we finally learned the actual reason he demanded to move  locations...Hear for yourself in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 13 June 2025

Two plant parents became one of our sweetest Second Date Update calls we’ve done all year, and even better we’ve got an update on their situation coming up in the podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 June 2025

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.

Transcribed - Published: 11 June 2025

Is it ever okay to date your friends EX? Don’t ask us, in fact, just get ‘em on the phone for an Awkward Tuesday Phone Call instead!See omnystudio.com/listener for privacy information.

Transcribed - Published: 10 June 2025

A quick trip to move his car ended up being a HUGE mistake for our listener, and it sent his date WILDLY OFF TRACK. Hear how it went down in a brand new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 9 June 2025

We've got a special new episode you this weekend! Normally on this show we try to HELP make a romantic connection but coming in today’s Textual Healing one listener wants us to make it clear she wants NOTHING to do with a guy that’s supposed to come over to her house later!See omnystudio.com/listener for privacy information.

Transcribed - Published: 8 June 2025

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 podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 7 June 2025

One of our listeners invited her date back to her place and spent HOURS together… but what she saw him do… she’s STILL trying to process. Hear what she went through in a new Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 6 June 2025

If you’re looking for a unique, innovative and new move to pick up women, you need to catch today’s Second Date Update with a guy who swears his tactic worked (at least ONCE).See omnystudio.com/listener for privacy information.

Transcribed - Published: 4 June 2025

One of our listeners is dealing with a difficult type of neighbor drama. You’re gonna want to hear our advice coming up in a brand new Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 3 June 2025

One of our listeners wishes she could take back what she said 11 months ago to a guy she went out with. It took her a year to realize her mistake, and now she wants another chance in a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 2 June 2025

We've got a special new episode you this weekend! It’s easy to say yes to some things, but saying YES to your EX is another story… After today’s call you’re never gonna look at ESCAPE ROOMS the same again. It’s SAY YES TO THE EX!See omnystudio.com/listener for privacy information.

Transcribed - Published: 1 June 2025

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 should have been his first red flag, now he wants our help in your Second Date Update. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 31 May 2025

A mysterious handwritten note was dropped onto the table during our listener's date and it altered both of their lives forever! Hear what it said coming up in a new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 30 May 2025

One of our listeners is confused after his date ended in the WEIRDEST way ever… but he still has SOME interest, so it couldn’t be that bad. Hear the brand new Second Date Update in the podcast! Get your 2nd Date Update Merch For A Cause HERE! See omnystudio.com/listener for privacy information.

Transcribed - Published: 28 May 2025

One of our listeners was SHOCKED by the children’s birthday invite her son received… in fact, all the parents were so bothered by the strange instructions, she needs our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 27 May 2025

In the podcast you can hear the SHOCKING and UNFORTUNATE events that happened during our Second Date Update – and they were all totally Brooke’s fault! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 26 May 2025

We've got a special new episode you this weekend! Can you figure out which of these embarrassing stories from our high school days are true and which ones are lies? It’s TRUE CONFESSIONS!See omnystudio.com/listener for privacy information.

Transcribed - Published: 25 May 2025

One of our listeners is FURIOUS after her date left her in the most embarrassing situation of her life… and now she wants not just answers, but REVENGE. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 24 May 2025

One of our listener’s first kiss happened but her second date never did! So we’re gonna do everything in our power to get to the bottom of it in a brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 21 May 2025

One of our listeners came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the most awkward roommate convo of her life!See omnystudio.com/listener for privacy information.

Transcribed - Published: 20 May 2025

When a listener describes his date as an "unconventional beauty", we're going to try to uncover if that's the reason she isn't calling him back!See omnystudio.com/listener for privacy information.

Transcribed - Published: 19 May 2025