Brooke and Jeffrey: Second Date Update

Part 1 After we totally botched a Second Date for a guy a few months ago, he’s back and at this point we’re not sure if he’s trolling us or just likes the punishment. We can't let him down this time! Part 2 Imagine if you went on a date with a coworker and after the hang out, MULTIPLE PEOPLE are now avoiding you. It happened to one of our listeners and you can hear why in a Secon...

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

It’s one of the most controversial segments in the history of our show, but today it comes with a twist. It's the Holiday Edition of Brooke Breaks You Up! See omnystudio.com/listener for privacy information.

The most annoying part of dating apps is all the wasted energy you put in, only to never actually meet up in person… But our listener on the phone says he has a method to eliminate that headache! See omnystudio.com/listener for privacy information.

What if a family member overhears something they weren't supposed to, and now the holidays are going to be EXTRA WEIRD unless you make a phone call with our help? It's happening right here in your Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners made her date laugh so hard that something embarrassing slipped out and she’s worried it’s the reason he’s not calling back! See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd 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, December 10th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok Brookea...

Part 1 The guy on the phone today told us he’s fed up with being friend-zoned, and he wants to get ahead of things with a bizarre new plan we’ve never tried before!  Part 2 The guy on the phone says a random child walked up to their table during a romantic dinner and said something that threw off their ENTIRE EVENING. Is a kid really to blame for him not getting a Second Date? See...

One of our listeners made a BIG ASK, a request we never heard before… telling a guy if he wanted any shot at dating her, he had to do THIS first. Find out what it is in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

One of our listeners is having a problem dealing with her next door neighbor and it’s slowly ruining her life. We’ll try to help her with some Textual Healing! See omnystudio.com/listener for privacy information.

One of our listeners says there's a sneaky spot where you can meet cute guys, and it ONLY happens during the holidays. You’ll find out where that is coming up in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

The woman on the phone today is ready to CONFRONT the person who has been scamming her for the past 3 years. It also happens to be her boyfriend… See omnystudio.com/listener for privacy information.

It can be so difficult to find a guy who does the bare minimum, but the woman on the phone today found a guy who is OUT OF THIS WORLD! We’ll let her explain why she wants to see her date again, in your Second Date Update podcast! See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd 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, December 3rd, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok Brookean...

Part 1  One of our listeners met a guy in a peculiar way… by SAVING HIS LIFE! But why doesn’t he ever want to see her again? We’ll use a Second Date Update to find out. Part 2 The woman on the phone today was SHOCKED when she got a look inside her date's home and saw what he collects...Even though he swears it's for a good reason. Find out what it is in the podcast! See omn...

The guy on the phone today has HUGE regrets about asking his date about Ex...Yet he still wants our help getting in touch with her for a Second Date Update! See omnystudio.com/listener for privacy information.

The couple on the phone today got the most AWKWARD comment a server could say to a table when they first appeared on our show a few months ago. Now, they’re BACK to give us a special Second Date Update UPDATE! See omnystudio.com/listener for privacy information.

The woman on the phone today is CERTAIN that there is a logical explanation for why her date suddenly dropped off the face of the earth after ten days… We’re gonna help her KEEP HOPE ALIVE in your Second Date Update podcast!  See omnystudio.com/listener for privacy information.

Our listener says her boyfriend is TOO PERFECT, and it might be all her fault! It’s causing a problem that she wants to fix in a brand new Awkward Tuesday Phone Call! See omnystudio.com/listener for privacy information.

One of our listeners wanted to sweep his date off her feet….. but based on the reactions we got in this room to his grand romantic gestures there’s a chance he MAY have overdone it… See for yourself in the Second Date Update podcast! See omnystudio.com/listener for privacy information.

We're trying out a new idea for our fans of the 2nd 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: Monday, November 24th, 2025 Curious if we look as bad as we sound? Follow us @BrookeandJeffrey: Youtube Instagram TikTok BrookeandJ...

Part 1 One of our listeners said he changed ONE THING on his dating profile that instantly changed the game for him. He wishes he’d done this years ago and you can hear what it is in the Second Date podcast. Part 2  Out of every Second Date we’ve done this year, today's might be the most MEMORABLE of the bunch. See omnystudio.com/listener for privacy information.

One of our listeners says he got his inspiration for his dating “MOVE” by watching on video online and gathering the courage to try it himself. Hear what it was in a Second Date podcast! See omnystudio.com/listener for privacy information.

The holidays nearly broke up the couple on the phone today when they first dated a year ago. But now with the yuletide season coming up were going to reconnect with them for a special update! See omnystudio.com/listener for privacy information.

The guy in today’s Second Date Update has been on the show before, but today he gets the special opportunity for a First Date REDATE! See omnystudio.com/listener for privacy information.