Brooke and Jeffrey: Second Date Update

When we offered to send this couple on another date that WE PAY for, we never expected to get the answer back that we received. Hear one of the most bizarre endings to a Second Date Update ever! See omnystudio.com/listener for privacy information.

One woman has kept a secret from her bridal party for the last 6 years, and it probably explains why she cut contact with all of them the day after the wedding! See omnystudio.com/listener for privacy information.

Brian had so much fun on his date with Ariel, that at one point they were feeding each other food like animals! So, why isn’t she calling him back for more animal-style love? We’ll find out in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners needs our help desperately before his apartment is completely EMPTY of all his belongings. He thinks his girlfriend has something to do with it, but he won’t know how to talk to her until we do an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Mike and Chrissy’s first date sounded like the start of a horror movie… Why was a mysterious stranger watching them silently the whole time?? We needed more details in the Second Date Update podcast! See omnystudio.com/listener for privacy information.

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: Thursday, October 1st, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Part 1 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. Part 2 For one of our listeners, the hottest thing that happened on her date was a game of CHARADES! See omnystudio.com/listener for privacy information.

Hannah says that she and her date got into TWO arguments before they even got out of her driveway! Why would she even want to see him again? She’ll explain in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Out of all the Second Date Updates we’ve done in 2026, this one might have been the most viral! And we’ve got the couple back for a long awaited Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

Vince is on the phone for a Second Date Update and he says the intimate parts of his relationship with Jamie are great but he want’s our help getting MORE SERIOUS than he’s ever been before! See omnystudio.com/listener for privacy information.

Last week we promised a guy that we’d help him come clean about losing his job and lying about it to his fiancé… but he snuck in another bombshell we didn’t see coming! Hear what it was during your Awkward Tuesday Phone Call podcast! See omnystudio.com/listener for privacy information.

The guy on the phone for today’s Second Date Update isn’t getting a call back, and it’s probably because the woman he’s interested in was on a DATE with ANOTHER MAN! He swears he can explain in the podcast! See omnystudio.com/listener for privacy information.

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: Tuesday, September 22nd, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Part 1 The guy on the phone today decided he would surprise his date with an unexpected guest during their dinner… Hear who it was in the podcast! Part 2 The guy in today’s Second Date clearly got his idea for a date from listening to our show, and we might owe him an apology, or at least some help trying to get another one! See omnystudio.com/listener for privacy information.

Jack managed to secure a night over at Sarah’s place, but she CAUGHT HIM on the couch doing something he shouldn’t in the MIDDLE of the night! Find out what happened in your Second Date Update! See omnystudio.com/listener for privacy information.

One of our listeners thinks he has the chance to take the TRIP of a LIFETIME with one of his co-workers… if we can give him the right advice in your Awkward THURSDAY Phone Call! See omnystudio.com/listener for privacy information.

Cody admits “MISTAKES WERE MADE” on his date with Tiz. But, despite his failings he’s ready to reach out and try to make a better love connection in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

How do you tell a close friend to get out of your house forever without ruining the friendship? We’ll try to figure it out the hard way during your Awkward Tuesday Phone Call podcast! See omnystudio.com/listener for privacy information.

Tracy gave Rob a VERY specific place he had to go in order to score a date with her. Was it worth his effort? Let’s find out in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

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: Thursday, September 17th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Part 1 One of our listeners did something THREE different times during their date… and while once might be strange, at the end it all made sense. Part 2 One of our listeners admits SHE did something stupid, just to MEET a guy. Was it her idea? No. Was it effective? Let's find out! See omnystudio.com/listener for privacy information.

Beth is regretting rejecting Eddie, who happened to be wearing a certain “fashion accessory” and now she wants a do-over! We’ll see what magic we can work in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

We've seen the texts and comments and we couldn't let Summer end without the "You Wouldn't Dare Summertime Challenge" happening! It's all going down at one time, in studio and there's some mystery meals ready for each and every host! See omnystudio.com/listener for privacy information.

The guy in today’s Second Date Update secretly planned a very informative and special date night for the woman he’s interested in. It’s one of the MOST ORIGINAL date ideas we’ve ever heard. See omnystudio.com/listener for privacy information.

One of our listeners is CERTAIN that the universe was talking to her when she met her DREAM MAN. The only problem? They kind met during a disaster and now she wants our help cleaning up after it! It's your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

The woman in today’s Second Date Update knows she didn’t give strong signals to the guy she’s interested. In fact, she stayed FAR AWAY from him the whole night! We’ll dig into why in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

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: Thursday, September 10th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Part 1 One of our listeners came up with one of the CLEANEST & MOST FUN ice breaker questions we’ve ever heard… Part 2 The woman on the phone today described her date like a very famous film, but the comparison immediately had us all very concerned. See omnystudio.com/listener for privacy information.

SOMEONE drops the “L-word” on today’s upcoming Second Date Update and the only thing weirder than them saying it, is what happened the next day! See omnystudio.com/listener for privacy information.

SPEED was definitely a factor in Roman and Hailey’s blossoming relationship when they were first on our show months ago. But, today they’re back to fill us in and what’s happened since then in a Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

One of our listeners tried a new way to meet single guys in real life, and she found herself in a dark room FULL of eligible bachelors! Hear about the surprising guy that she connected with in your Second Date Update! See omnystudio.com/listener for privacy information.

One overbearing mother got her son’s teacher to send an email to every parent in the class, and the drama its caused has shaken the school to its core and sucked us in for an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

What one of our listeners did in a public park during her first date was definitely FREAKY. So much so, that it had us in studio wilding out! See omnystudio.com/listener for privacy information.

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: Thursday, September 3rd, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: YouTube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Part 1 Abbey had dates with TWO different guys, but could only pick one to pursue. Did she choose correctly? Part 2 Miles’s closing move with Zoey was not only fun and flirtatious, it also comes with pizza. We guarantee guys are gonna try and steal this… See omnystudio.com/listener for privacy information.

One of our listeners felt INSTANT REGRET during his date and even tried to BAIL as soon as it started… But he stuck it out and now he wants our help with a Second Date Update! See omnystudio.com/listener for privacy information.

After 7 years apart we’re going to TRY to help one listener overcome the biggest romantic mistake he’s ever made, starting with getting his ex on the phone with us! See omnystudio.com/listener for privacy information.

Not all surprises are good surprises, and one of our listeners found that out the hard way! Hear what kind of trouble Ava and Dean found themselves in, in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners was alone and had the urge to open his significant other’s computer, and what happened next lead to possible the most shocking Awkward Tuesday Phone Call of the year! See omnystudio.com/listener for privacy information.

Bobby didn’t come across in the best way the FIRST time he was on our show, but this time he SWEARS he’s changed and is now deserving of our help with a Second Date Update! See omnystudio.com/listener for privacy information.

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: Tuesday, August 25th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

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 gone to before! See omnystudio.com/listener for privacy information.

The guy in today’s Second Date was willing to do something that took A LOT of patience, selflessness, and understanding… hear if his sacrifice was worth it in the podcast! See omnystudio.com/listener for privacy information.

Two of our listeners will test the waters and see if they connect romantically when they speak to each other for the first time on our show! See omnystudio.com/listener for privacy information.

In today’s Second Date we learned about a dating app that NONE of us had even heard of before, and even though we were skeptical.. it helped one of our listener's secure his match! See omnystudio.com/listener for privacy information.

Imagine getting a text from your ex you haven’t seen in a year and she’s ECSTATIC about the WORST NEWS POSSIBLE… It happened to one of our listeners and he needs our advice in an Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners says he got a singular one-word text that let him know he BADLY screwed up his first date. See omnystudio.com/listener for privacy information.

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: Tuesday, August 18th, 2026 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJeffrey.com See omnystudio.com/listener for privacy information.

Part 1 Cory took a PLANE FLIGHT to hang out with Alison… but their date left a lot to be desired… We’ll try to fix their future in your Second Date Update podcast! Part 2 One of our listeners took a BOLD step when she made a move on a guy while he was working… and seconds later they were inside her place getting familiar. See omnystudio.com/listener for privacy information.

Sasha is on the phone for today’s Second Date Update and she thinks the guy who left her his number is either her soulmate or a COMPLETE Scum Bag! Lucky for her, we've got a very special way to unveil the truth… See omnystudio.com/listener for privacy information.