Brooke and Jeffrey: Second Date Update

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

We've got a special new episode you this weekend! One of our listeners caught his neighbor doing something that's making him very uncomfortable... it's happened MULTIPLE times and he feels like he's gotta say something... but he can't do it in person so we had him on for some Textual Healing!See omnystudio.com/listener for privacy information.

Transcribed - Published: 18 May 2025

One of our listeners managed to make a genuine connection with a woman, all because of one trick he’s been using for YEARS! Hear what it is in your Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 17 May 2025

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 privacy information.

Transcribed - Published: 16 May 2025

Today is proof that just because we think a relationship is doomed doesn't mean anything... because one of the most unexpected couples we've had on our show are BACK for a Second Date Update UPDATE! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 May 2025

When you're out to dinner and you notice something on your date's face, do you tell them or keep it to yourself? One of our listeners is worried the choice he made is why he's not getting a call back. We'll find out 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: 14 May 2025

One of our listeners met a guy at a house party and says he literally RISKED HIS LIFE to not get caught with her! Now she wants answers! We're going to help her in a brand new Awkward Tuesday phone call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 13 May 2025

One of our listeners says she experienced an intimate moment with a guy she’d never met, when they were in a crowded coffee shop at the same time… and It was definitely more than just flirty eye contact. We're going to hear how that transpired into a whole afternoon together in your brand new Second Date Update! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 May 2025

We've got a special new episode you this weekend! One of our listeners got dumped a few months ago during an argument about TOENAILS... But now, he swears he's changed and can PROVE IT. We've got his ex- girlfriend on the phone in hopes to get him another chance in a brand new Say Yes to the Ex!See omnystudio.com/listener for privacy information.

Transcribed - Published: 11 May 2025

If only finding a date was as easy as ordering your favorite drink. One of our listeners had the perfect girl right in front of him all thanks to a new dating event that even YOU might want to try! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 10 May 2025

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 Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 9 May 2025

One of our female listeners used an innocent little excuse…. To go from awkward end of the night hug… to Instant sleepover at his place… Your gonna hear it in your brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 7 May 2025

One of our listeners is facing a huge moral dilemma, does she mind her own business, or possibly ruin her friends relationship?See omnystudio.com/listener for privacy information.

Transcribed - Published: 6 May 2025

One of our listeners turned a super awkward moment into an actual MEET CUTE that almost seemed TOO perfect. You’ll hear it in a brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 5 May 2025

We've got a special new episode you this weekend! Two single listeners will meet for the very first time on our show SIGHT UNSEEN… to see if chemistry bubbles up like the jets of a jacuzzi. It's a brand new “Blind Love Is!”See omnystudio.com/listener for privacy information.

Transcribed - Published: 4 May 2025

Someone’s phone alarm going off in the middle of the date set off the WILDEST part of their entire evening. Hear what it was for in your Second Date podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 3 May 2025

One of our listeners says HIS DATE asked him to do something UNUSUAL shortly after they sat down, and he thinks its part of why he’s not getting a call back. Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 2 May 2025

Something happened to our listener on his way to the first meetup with his date, and it changed the trajectory of their entire night! Hear what happened in a new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 30 April 2025

Our listeners love dysfunctional relationships so much, we didn't wanna deprive you. Here's a segment from our Full Show feed, 'Brooke and Jeffrey',  that may have even more drama than a Second Date Update. Let us know what you think!  What do you say to your best friend if you know they’re about to make the biggest mistake of their life? Find out what we suggest coming up in a new Awkward Tuesday Phone Call podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 29 April 2025

We were shocked when we heard about our listeners tense situation that went down on a first date with an UNEXPECTED VISITOR… You’ll hear how we help him in a brand new Second Date Update podcast! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 28 April 2025

We've got a special new episode you this weekend! One of our listeners is having communication issues with her relationship, but it’s not as simple as you’d think. We’ll help her get her man to say EXACTLY what she needs to hear coming up in a “SAY YES TO THE EX”See omnystudio.com/listener for privacy information.

Transcribed - Published: 27 April 2025

We had to try our best to get the woman on the phone to tell us the TRUTH about what happened on her date… and it might be the most embarrassing story of the year! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 26 April 2025