Brooke and Jeffrey: Second Date Update

Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Wednesday, June 24th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 28 June 2026

Part 1 One of our listeners claims they’ve discovered the GOLDEN pick-up line, hear what it is in your Second Date Update! Part 2 If someone messed up your coffee order, would you politely let them know or go scorched-earth instead? It happened to one of our listeners and their response got the attention of the entire room!See omnystudio.com/listener for privacy information.

Transcribed - Published: 27 June 2026

One of our listeners botched her date after trying to give him an honest compliment…. Hear how we tried to help her out her problem in a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 26 June 2026

One of our listeners is soon to be married and she’s already made half her friends and family angry. Is she at fault or are they overreacting?See omnystudio.com/listener for privacy information.

Transcribed - Published: 25 June 2026

Sometimes in the dating world, you have to decide if the pursuit is WORTH the prize at the end of the journey. In today’s Second Date Update we’re figuring out just HOW FAR one man will go for just one, single date. See omnystudio.com/listener for privacy information.

Transcribed - Published: 24 June 2026

One of our listeners trusted his “idiot” friend to help cover for him, and now he could be out of an apartment AND a girlfriend. We’ll try to save him in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 23 June 2026

One of our listeners told us he was STRUGGLING to get his date back on track after a few early fumbles, until a COMPLETE STRANGER swooped in and changed everything with one simple sentence! See omnystudio.com/listener for privacy information.

Transcribed - Published: 22 June 2026

Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Thursday, June 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 21 June 2026

Part 1 Can a guys job be a red flag? The woman in today’s Second Date met her guy at his red flag job, and she decided against her better judgment to go after him anyway! Part 2 Samantha 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.See omnystudio.com/listener for privacy information.

Transcribed - Published: 20 June 2026

One of our listeners got maybe the worst possible response to an unsolicited text message… EVER!See omnystudio.com/listener for privacy information.

Transcribed - Published: 19 June 2026

It’s a favorite of the listeners and the bane of Brooke’s existence… We’re doing another edition of “BROOKE BREAKS YOU UP!”See omnystudio.com/listener for privacy information.

Transcribed - Published: 18 June 2026

Josh tried to be funny to impress Lisa on their date and that plan BACKFIRED so badly, he found himself apologizing to a random 9 year old and his family. Hear how his humor got him in trouble in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 17 June 2026

We got BLINDSIDED by one of the BIGGEST LIES in the history of this show. It’s a complicated relationship problem and we’re doing our best to navigate it in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 16 June 2026

One of our listeners took his date to a ball game and INSTANTLY she was set off on a bad mood. He doesn’t know what sparked it but we’re on his side and we’re gonna dig in, when we do a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 June 2026

Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, June 12th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 14 June 2026

Part 1 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! Part 2 What do you do when someone suddenly STOPS replying to your texts? One of our listeners did something a little UNUSUAL to get his crush’s attention.See omnystudio.com/listener for privacy information.

Transcribed - Published: 13 June 2026

One of our listeners has a SYSTEM to get a date with ANY woman you want. But some of his tactics were so controversial, it nearly BROKE Brooke! See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 June 2026

We’ve had “Momma’s boys” and women with “Daddy Issues” on our show before but today we’re reconnecting with a DIFFERENT type of Red Flag that involves a third type of family member… It’s a special Second Date Update UPDATE where if you listen until the end we check in with the couple and how things have gone since they first appeared on our show!See omnystudio.com/listener for privacy information.

Transcribed - Published: 11 June 2026

Andrew overheard two woman saying something so SHOCKING & RUDE that he had to step in. He thinks he was heroic, but was it actually creepy? See omnystudio.com/listener for privacy information.

Transcribed - Published: 10 June 2026

A HUGE surprise is in total JEOPARDY and Olivia has turned to us for help! We’ll do our best to keep things on track in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 9 June 2026

One of our listeners says the woman he went out with wanted something VERY SPECIFIC whispered into her ears and it had him thinking “This woman is THE ONE!” Find out what that was coming up in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 8 June 2026

Every Sunday, we host one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, June 5th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 7 June 2026

Part 1 Rez DEFINITELY regrets a story he told Katrina on their date, and you’re gonna want to hear how he tells it in the Second Date Update! Part 2 One of our listeners is looking for all the help he can get locking down another hang out with a VERY classy woman.See omnystudio.com/listener for privacy information.

Transcribed - Published: 6 June 2026

Is a gift ever okay on the first date? Does it say too much or go too far? We go to the bottom of that question and got way more than we bargained for in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 5 June 2026

Maria is caught in a complicated entanglement of the modern dating scene and she wants our help to UNCOMPLICATE it in the weirdest way possible. It's your Textual Healing Podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 4 June 2026

We’ve heard some strange dealbreakers before on this show, but NOTHING has us as confused as the dealbreaker Kai had for Amy in today’s Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 3 June 2026

Our listener, Juliana, let something slip at the WRONG moment and now she wants our help getting her situationship back on track! We’ll do our best in the Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 2 June 2026

Blake didn’t spend ANY money on his date with Ashley, in fact, he actually MADE money in a way that’s 100% legal. You’ll hear how in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 1 June 2026

Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, May 29th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 31 May 2026

Part 1  One of our listeners realized she’s been approaching dating apps the wrong way… and one piece of advice completed shifted her romantic life. Part 2 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 Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 30 May 2026

One of our listeners showed up to his co-workers “DIVORCE PARTY” and while the theme was a bit strange, the romance levels were surprisingly high and now we’re gonna help him get ahold of the woman he met there in your Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 29 May 2026

Two of our listeners told us about “European Dating” and it led to one of the most popular Second Date Updates of the year! Now, they’re back on again for a special UPDATE UPDATE!See omnystudio.com/listener for privacy information.

Transcribed - Published: 28 May 2026

Jay let Allie know IMMEDIATELY what ONE THING has been a deal breaker, about his past… He thought she would appreciate it, but now he’s asking us for a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 27 May 2026

One of our listeners told us her grandma is getting KICKED OUT of her senior home. It’s a unique circumstance and now she wants our help with an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 26 May 2026

One of our listeners admits she broke more than FIVE unwritten rules of dating, but she says she had a good reason too! See omnystudio.com/listener for privacy information.

Transcribed - Published: 25 May 2026

Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Monday, May 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 24 May 2026

Part 1 One of our listeners went down a weird internet rabbit hole and what she found changed her whole approach to dating… Hear what she learned in your Second Date Update! Part 2 The guy on the phone today tried a UNIQUE STRATEGY to extend his date.… and even he admits, it was WAY more cringe than he thought it would be…See omnystudio.com/listener for privacy information.

Transcribed - Published: 23 May 2026

There’s no EASY way to approach an attractive person on public transportation, and that was exactly the case for our listener! She’ll tell us her story and how she wants to get in touch with a guy she met on the train coming up in a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 22 May 2026

Normally, we help people get second dates after a first one, but today we’re helping a guy who hasn’t even had ONE date with the woman he’s interested, and he wants to jump straight into a relationship!See omnystudio.com/listener for privacy information.

Transcribed - Published: 21 May 2026

One of our listeners says he DEFINITELY has someone to thank for his unforgettable date night. But the weird part is… that person isn’t exactly ALIVE… See omnystudio.com/listener for privacy information.

Transcribed - Published: 20 May 2026

We’re dealing with an INTERNATIONAL ROMANCE EMERGENCY in today’s Awkward Tuesday Phone Call! We’re putting all our efforts behind getting one woman to FINALLY pick up the phone for her boyfriend…See omnystudio.com/listener for privacy information.

Transcribed - Published: 19 May 2026

Our listener on the phone today went out of his way to do the KIND, HONEST, and RESPECTFUL thing for his date… but it ended him up here with us and out of luck and love! Luckily, we can help him with a Second Date Update!See omnystudio.com/listener for privacy information.

Transcribed - Published: 18 May 2026

 Every Sunday, we will be hosting one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Wednesday, May 13th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 17 May 2026

Part 1 One of our listeners had the SHOCK OF A LIFETIME after being set up on a blind date by her friend. As soon as she showed up she knew something was very wrong… Part 2 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.See omnystudio.com/listener for privacy information.

Transcribed - Published: 16 May 2026

The woman on the phone today shared a SHOCKING secret in today’s Second Date Update. We were cool with it at first but by the end of the call our jaws were on the floor! See omnystudio.com/listener for privacy information.

Transcribed - Published: 15 May 2026

Ashwin and Sierra came on our show a while back and we got SO many comments asking for more info, we HAD to bring them back for a Second Date Update UPDATE! Stay tuned to the end to hear from both of them and how their romance has gone since last time they spoke with us!See omnystudio.com/listener for privacy information.

Transcribed - Published: 14 May 2026

One of our listeners refused to do things the easy way, and after he complicated drinks with his date, he thinks he knows the reason she’s not calling him back! We’ll see if he’s right in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 13 May 2026

One of our listeners found out what his girlfriend has been SECRETLY planning to give him for his birthday and he says he needs to STOP her IMMEDIATELY. Hear why in your Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Transcribed - Published: 12 May 2026

Our listener on the phone thinks that the reason he's not getting a call back is because of an argument he got into with a cashier during their date. He says it’s totally justified but he wants our assistance explaining! We'll do just that in the Second Date Update Podcast!See omnystudio.com/listener for privacy information.

Transcribed - Published: 11 May 2026

Every Sunday, we host one of our FULL HOUR episodes from our main show feed, Brooke & Jeffrey! We'd love to hear your feedback...but please send all negative reviews to Jeffrey. FULL SHOW: Friday, May 8th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.comSee omnystudio.com/listener for privacy information.

Transcribed - Published: 10 May 2026