Brooke and Jeffrey: Second Date Update

Daniel was DESPERATELY trying to avoid answering one specific question on his date with Lilly. It got asked, it DIDN’T go well, and now he wants our help figuring out how to put the pieces back together in your Second Date Update! See omnystudio.com/listener for privacy information.

The guy on the phone for today’s Awkward Thursday Phone Call DESPERATELY needs our help because his HOA is threatening to FINE him hundreds of dollars if he goes through with his favorite Halloween tradition! See omnystudio.com/listener for privacy information.

One of our listeners has a crush on his co-worker and he came up with a plan to show her! It involves a microwave and a wilted bowl of salad… See omnystudio.com/listener for privacy information.

Two weeks after tying the knot, Katherine wants an apology from one of her unruly family members for the way he acted at her wedding. Its your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

Susan said her date asked her a STRANGE question at the end of the night and was VERY disappointed by her response… You’ll hear the question and her answer in your 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: Friday, October 16th, 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 Nick is willing to tell us the MOST EMBARRASSING date night of his life… in hopes it will get him another shot with the woman he loves. Will it be worth the humiliation? Part 2 We have NO IDEA who we’re dialing in today’s Second Date Update, we have a number, and a sneaking suspicion it might be a trap but only one way to find out! See omnystudio.com/listener for privacy information.

Kyle made ONE SLIGHT adjustment to his dating profile and he ended up matching with a woman he calls “The real deal.” So why does he need our help? We’ll figure it out in your Second Date Update! See omnystudio.com/listener for privacy information.

You may remember Brian and Olivia as a “Disney DO & Disney DON’T” couple where he was super into all things Disney and she was open to learning more…. But where are they now MONTHS after they first appeared on the show? Find out in your Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

What’s the most embarrassing thing your date could catch you doing? David got caught at a bad time RIGHT as his date was meeting up with him and it happened AGAIN later on. We’ll help him try to recover in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

Meeting your girlfriend’s parents can be stressful! It happened to Simon over a month ago, so why NOW does he need our help “fixing” what he says went wrong? Find out in a new Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

In today’s Second Date Update we found ourselves in the middle of a problem that is WAY out of our price range, even Brooke’s! 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 8th, 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 5 minutes into his date with Delilah, Jack realized he forgot something MAJORLY important. Hear what slipped his mind and how we’re helping him gain back ground! Part 2 The listener in today’s Second Date Update says that if we can’t help him, it’ll be the first time EVER that he’s been rejected by a woman! See omnystudio.com/listener for privacy information.

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.